Tag: 99.1741

Solanum alkaloids. L. Optical rotatory dispersion and circular dichroism. 1. Dithiourethans of cyclic amines was written by Ripperger, H.;Schreiber, K.. And the article was included in Tetrahedron in 1965.Synthetic Route of C6H13N This article mentions the following:

The dithiourethans of substituted piperidines with an asym. C atom were prepared and their optical rotatory dispersion as well as their circular dichroism were measured. The uv, O.R.D. and circular dichroism spectra were measured at 20° in dioxane. The amine (1 mole), 8 moles Et₃N and CS₂ in alc. kept 30 min. at 50° and 1 hr. at 50° after addition of 16 moles MeI and the mixture evaporated at 50° in vacuo gave the corresponding dithiourethans. The compounds were very unstable and could not be purified chromatographically on Al₂O₃. Resolution with L-tartaric acid gave 0.99 g. (R)-α-pipecoline, m. 118-21°, [α]¹⁹_D -31.8°, converted in 20 ml. alc. and extracted with Et₂O to yield 44% (R)-N-dithiocarbomethoxy-α-pipecoline, b_1.0 150-60°. Conhydrine (143 mg.), m. 119-20°, [α]²⁰_D 9.9° (95% alc.) treated as above using 2 ml. EtOH and the product decomposed with H₂O and extracted with Et₂O yielded 14% N-dithiocarbomethoxyconhydrine, m. 25°. Conversion of 104 mg. (22S, 25R)-22,26-imino-5α-cholestane-3β,16β-diol using 30 ml. alc. yielded 46% N-dithiocarbomethoxydihydro-5α-solasodan-3β-ol A, m. 203-5°. Dioxane (10 ml.) containing 104 mg. (22S, 25S)-22,26-imino-5α-cholestane-3β,16β-diol kept 15 hrs. at 20° with 10 mg. NaOH in 0.25 ml. H₂O and 21 mg. CS₂, the mixture treated 15 hrs. at 20° with 145 mg. MeI and evaporated at 50° in vacuo yielded 54% N-dithiocarbomethoxydihydro-5α-tomatidan-3β-ol A, m. 133-6°, (R)-Pipecolinic acid (1 millimole), m. 264°, [α]²⁰_D 28° (H₂O) in 3 ml. H₂O shaken 1 hr. at 20° with 2 ml. N NaOH and 114 mg. CS₂ and the mixture shaken 2 hrs. with 218 mg. MeI, the Et₂O-washed solution decomposed with 1 ml. N HCl and extracted with Et₂O yielded 52% (R)-N-dithiocarbomethoxypipecolinic acid, m. 88.0-90.5°. Dihydro-5α-tomatidan-3β-ol B (104 mg.) converted in the presence of 10 ml. alc. yielded 35% N-dithiocarbomethoxydihydro-5α-tomatidan-3β-ol B, m. 143-5°. The molar amplitude, a, of the O.R.D. curves and the maximum molar ellipsity, [θ]_maximum, of the dithiourethans were tabulated. The range of compounds investigated suggested that only the asym. at the α-C atom was important in determining the sign of the Cotton effect, and this correlation appeared to be generally useful in the assignment of the absolute α-configuration of cyclic amines. In the experiment, the researchers used many compounds, for example, (R)-2-Methylpiperidine (cas: 1722-95-8Synthetic Route of C6H13N).

(R)-2-Methylpiperidine (cas: 1722-95-8) belongs to piperidine derivatives. Piperidine is a metabolite of cadaverine, a polyamine found in the human intestine. Some chemotherapeutic agents have piperidine moiety within their structure, foremost among them, vinblastine and raloxifene.Synthetic Route of C6H13N

Referemce:
Piperidine – Wikipedia,
Piperidine | C5H11N – PubChem

Sensitive enantiomeric separation of aliphatic and aromatic amines using aromatic anhydrides as non-chiral derivatizing agents was written by Pawlowska, Maria;Zukowski, Janusz;Armstrong, Daniel W.. And the article was included in Journal of Chromatography A in 1994.SDS of cas: 1722-95-8 This article mentions the following:

New pre-column derivatizing reagents: phthalic anhydride, 3-nitrophthalic anhydride, diphenic anhydride, 1,8-naphthalic anhydride and diphenylmaleic anhydride have been developed for resolving chiral compounds having amine groups. Although all of these agents produce derivatives with high molar absorptivities, the later two also fluoresce. Upon derivatization, aromatic analytes containing free carboxylic groups are produced. Both of these moieties enhance chiral recognition on cyclodextrin-based columns. The derivatization reaction is carried out at room temperature by shaking a buffered aqueous solution of a sample with an acetonitrile solution of the reagent. The reaction is fast and proceeds without any detectable racemization. The labeled compounds have favorable chromatog. properties which are demonstrated by resolution of a number of chiral compounds on cyclodextrin-bonded phases operated with non-aqueous polar organic eluents. The selectivity and good efficiency of this system contributes to its high sensitivity and in its applicability for detecting low levels of enantiomeric impurities. The detection limit is in the picomole range and less than 0.1% enantiomeric impurities can be determined in some cases. In the experiment, the researchers used many compounds, for example, (R)-2-Methylpiperidine (cas: 1722-95-8SDS of cas: 1722-95-8).

(R)-2-Methylpiperidine (cas: 1722-95-8) belongs to piperidine derivatives. The piperidine structural motif is present in numerous natural alkaloids. These include piperine, which gives black pepper its spicy taste. Piperidine prefers a chair conformation, similar to cyclohexane. Unlike cyclohexane, piperidine has two distinguishable chair conformations: one with the N–H bond in an axial position, and the other in an equatorial position.SDS of cas: 1722-95-8

Referemce:
Piperidine – Wikipedia,
Piperidine | C5H11N – PubChem

¹H NMR Chiral Analysis of Charged Molecules via Ion Pairing with Aluminum Complexes was written by Seo, Min-Seob;Kim, Hyunwoo. And the article was included in Journal of the American Chemical Society in 2015.Electric Literature of C6H13N This article mentions the following:

Chiral anal., such as determination of identity, concentration, and relative ratio of optically active (chiral) mols., plays an indispensable role in contemporary synthetic, medicinal, and biol. chem. Here, we describe the selective control of metal-centered chirality in an octahedral geometry to prepare neg. charged Al^III complexes, which can be used as versatile ¹H NMR chiral solvating agents for both pos. and neg. charged chiral mols. in polar or nonpolar solvents. During the formation of ion pairs between the Al^III complexes and the chiral analytes such as amines and carboxylic acids, the metal-centered chirality in the Al complexes plays a crucial role in providing anisochronous chem. shifts to the ¹H NMR spectra. As a chiral solvating agent, Al^III complexes display an unprecedentedly broad substrate scope, good solvent compatibility, and operational simplicity. In the experiment, the researchers used many compounds, for example, (R)-2-Methylpiperidine (cas: 1722-95-8Electric Literature of C6H13N).

(R)-2-Methylpiperidine (cas: 1722-95-8) belongs to piperidine derivatives. The piperidine structural motif is present in numerous natural alkaloids. These include piperine, which gives black pepper its spicy taste. The piperidine and polyhydroxylated indolizidine derivatives have shown to be promising α-glucosidase inhibitors. The former are analogs of DNJ with an improved α-glucosidase inhibitory profile than that of DNJ. Boisson et al.Electric Literature of C6H13N

Referemce:
Piperidine – Wikipedia,
Piperidine | C5H11N – PubChem

In situ approach for testing the enantiopurity of chiral amines and amino alcohols by ¹H NMR was written by Mishra, Sandeep Kumar;Chaudhari, Sachin R.;Suryaprakash, N.. And the article was included in Organic & Biomolecular Chemistry in 2014.Formula: C6H13N This article mentions the following:

An in situ approach involving a simple mix and shake method for testing the enantiopurity of primary, secondary and tertiary chiral amines and their derivatives, chiral amino alcs., by ¹H-NMR spectroscopy is developed. The protocol involves the in situ formation of chiral ammonium borate salt from a mixture of C₂ sym. chiral BINOL, trialkoxyborane and chiral amines. The proposed concept was demonstrated convincingly on a large number of chiral and pro-chiral amines and amino alcs., and also aids the precise measurement of enantiomeric excess. The protocol can be completed in a couple of minutes directly in the NMR sample tube, without the need for any phys. separation In the experiment, the researchers used many compounds, for example, (R)-2-Methylpiperidine (cas: 1722-95-8Formula: C6H13N).

(R)-2-Methylpiperidine (cas: 1722-95-8) belongs to piperidine derivatives. Piperidine has a role as a reagent, a protic solvent, a base, a catalyst, a plant metabolite, a human metabolite and a non-polar solvent. Some chemotherapeutic agents have piperidine moiety within their structure, foremost among them, vinblastine and raloxifene.Formula: C6H13N

Referemce:
Piperidine – Wikipedia,
Piperidine | C5H11N – PubChem

Solanum alkaloids. L. Optical rotatory dispersion and circular dichroism. 1. Dithiourethans of cyclic amines was written by Ripperger, H.;Schreiber, K.. And the article was included in Tetrahedron in 1965.Synthetic Route of C6H13N This article mentions the following:

The dithiourethans of substituted piperidines with an asym. C atom were prepared and their optical rotatory dispersion as well as their circular dichroism were measured. The uv, O.R.D. and circular dichroism spectra were measured at 20° in dioxane. The amine (1 mole), 8 moles Et₃N and CS₂ in alc. kept 30 min. at 50° and 1 hr. at 50° after addition of 16 moles MeI and the mixture evaporated at 50° in vacuo gave the corresponding dithiourethans. The compounds were very unstable and could not be purified chromatographically on Al₂O₃. Resolution with L-tartaric acid gave 0.99 g. (R)-α-pipecoline, m. 118-21°, [α]¹⁹_D -31.8°, converted in 20 ml. alc. and extracted with Et₂O to yield 44% (R)-N-dithiocarbomethoxy-α-pipecoline, b_1.0 150-60°. Conhydrine (143 mg.), m. 119-20°, [α]²⁰_D 9.9° (95% alc.) treated as above using 2 ml. EtOH and the product decomposed with H₂O and extracted with Et₂O yielded 14% N-dithiocarbomethoxyconhydrine, m. 25°. Conversion of 104 mg. (22S, 25R)-22,26-imino-5α-cholestane-3β,16β-diol using 30 ml. alc. yielded 46% N-dithiocarbomethoxydihydro-5α-solasodan-3β-ol A, m. 203-5°. Dioxane (10 ml.) containing 104 mg. (22S, 25S)-22,26-imino-5α-cholestane-3β,16β-diol kept 15 hrs. at 20° with 10 mg. NaOH in 0.25 ml. H₂O and 21 mg. CS₂, the mixture treated 15 hrs. at 20° with 145 mg. MeI and evaporated at 50° in vacuo yielded 54% N-dithiocarbomethoxydihydro-5α-tomatidan-3β-ol A, m. 133-6°, (R)-Pipecolinic acid (1 millimole), m. 264°, [α]²⁰_D 28° (H₂O) in 3 ml. H₂O shaken 1 hr. at 20° with 2 ml. N NaOH and 114 mg. CS₂ and the mixture shaken 2 hrs. with 218 mg. MeI, the Et₂O-washed solution decomposed with 1 ml. N HCl and extracted with Et₂O yielded 52% (R)-N-dithiocarbomethoxypipecolinic acid, m. 88.0-90.5°. Dihydro-5α-tomatidan-3β-ol B (104 mg.) converted in the presence of 10 ml. alc. yielded 35% N-dithiocarbomethoxydihydro-5α-tomatidan-3β-ol B, m. 143-5°. The molar amplitude, a, of the O.R.D. curves and the maximum molar ellipsity, [θ]_maximum, of the dithiourethans were tabulated. The range of compounds investigated suggested that only the asym. at the α-C atom was important in determining the sign of the Cotton effect, and this correlation appeared to be generally useful in the assignment of the absolute α-configuration of cyclic amines. In the experiment, the researchers used many compounds, for example, (R)-2-Methylpiperidine (cas: 1722-95-8Synthetic Route of C6H13N).

(R)-2-Methylpiperidine (cas: 1722-95-8) belongs to piperidine derivatives. Piperidine is a metabolite of cadaverine, a polyamine found in the human intestine. Some chemotherapeutic agents have piperidine moiety within their structure, foremost among them, vinblastine and raloxifene.Synthetic Route of C6H13N

Referemce:
Piperidine – Wikipedia,
Piperidine | C5H11N – PubChem

Sensitive enantiomeric separation of aliphatic and aromatic amines using aromatic anhydrides as non-chiral derivatizing agents was written by Pawlowska, Maria;Zukowski, Janusz;Armstrong, Daniel W.. And the article was included in Journal of Chromatography A in 1994.SDS of cas: 1722-95-8 This article mentions the following:

New pre-column derivatizing reagents: phthalic anhydride, 3-nitrophthalic anhydride, diphenic anhydride, 1,8-naphthalic anhydride and diphenylmaleic anhydride have been developed for resolving chiral compounds having amine groups. Although all of these agents produce derivatives with high molar absorptivities, the later two also fluoresce. Upon derivatization, aromatic analytes containing free carboxylic groups are produced. Both of these moieties enhance chiral recognition on cyclodextrin-based columns. The derivatization reaction is carried out at room temperature by shaking a buffered aqueous solution of a sample with an acetonitrile solution of the reagent. The reaction is fast and proceeds without any detectable racemization. The labeled compounds have favorable chromatog. properties which are demonstrated by resolution of a number of chiral compounds on cyclodextrin-bonded phases operated with non-aqueous polar organic eluents. The selectivity and good efficiency of this system contributes to its high sensitivity and in its applicability for detecting low levels of enantiomeric impurities. The detection limit is in the picomole range and less than 0.1% enantiomeric impurities can be determined in some cases. In the experiment, the researchers used many compounds, for example, (R)-2-Methylpiperidine (cas: 1722-95-8SDS of cas: 1722-95-8).

(R)-2-Methylpiperidine (cas: 1722-95-8) belongs to piperidine derivatives. The piperidine structural motif is present in numerous natural alkaloids. These include piperine, which gives black pepper its spicy taste. Piperidine prefers a chair conformation, similar to cyclohexane. Unlike cyclohexane, piperidine has two distinguishable chair conformations: one with the N–H bond in an axial position, and the other in an equatorial position.SDS of cas: 1722-95-8

Referemce:
Piperidine – Wikipedia,
Piperidine | C5H11N – PubChem

¹H NMR Chiral Analysis of Charged Molecules via Ion Pairing with Aluminum Complexes was written by Seo, Min-Seob;Kim, Hyunwoo. And the article was included in Journal of the American Chemical Society in 2015.Electric Literature of C6H13N This article mentions the following:

Chiral anal., such as determination of identity, concentration, and relative ratio of optically active (chiral) mols., plays an indispensable role in contemporary synthetic, medicinal, and biol. chem. Here, we describe the selective control of metal-centered chirality in an octahedral geometry to prepare neg. charged Al^III complexes, which can be used as versatile ¹H NMR chiral solvating agents for both pos. and neg. charged chiral mols. in polar or nonpolar solvents. During the formation of ion pairs between the Al^III complexes and the chiral analytes such as amines and carboxylic acids, the metal-centered chirality in the Al complexes plays a crucial role in providing anisochronous chem. shifts to the ¹H NMR spectra. As a chiral solvating agent, Al^III complexes display an unprecedentedly broad substrate scope, good solvent compatibility, and operational simplicity. In the experiment, the researchers used many compounds, for example, (R)-2-Methylpiperidine (cas: 1722-95-8Electric Literature of C6H13N).

(R)-2-Methylpiperidine (cas: 1722-95-8) belongs to piperidine derivatives. The piperidine structural motif is present in numerous natural alkaloids. These include piperine, which gives black pepper its spicy taste. The piperidine and polyhydroxylated indolizidine derivatives have shown to be promising α-glucosidase inhibitors. The former are analogs of DNJ with an improved α-glucosidase inhibitory profile than that of DNJ. Boisson et al.Electric Literature of C6H13N

Referemce:
Piperidine – Wikipedia,
Piperidine | C5H11N – PubChem

¹H NMR Chiral Analysis of Charged Molecules via Ion Pairing with Aluminum Complexes was written by Seo, Min-Seob;Kim, Hyunwoo. And the article was included in Journal of the American Chemical Society in 2015.Electric Literature of C6H13N This article mentions the following:

Chiral anal., such as determination of identity, concentration, and relative ratio of optically active (chiral) mols., plays an indispensable role in contemporary synthetic, medicinal, and biol. chem. Here, we describe the selective control of metal-centered chirality in an octahedral geometry to prepare neg. charged Al^III complexes, which can be used as versatile ¹H NMR chiral solvating agents for both pos. and neg. charged chiral mols. in polar or nonpolar solvents. During the formation of ion pairs between the Al^III complexes and the chiral analytes such as amines and carboxylic acids, the metal-centered chirality in the Al complexes plays a crucial role in providing anisochronous chem. shifts to the ¹H NMR spectra. As a chiral solvating agent, Al^III complexes display an unprecedentedly broad substrate scope, good solvent compatibility, and operational simplicity. In the experiment, the researchers used many compounds, for example, (R)-2-Methylpiperidine (cas: 1722-95-8Electric Literature of C6H13N).

(R)-2-Methylpiperidine (cas: 1722-95-8) belongs to piperidine derivatives. The piperidine structural motif is present in numerous natural alkaloids. These include piperine, which gives black pepper its spicy taste. The piperidine and polyhydroxylated indolizidine derivatives have shown to be promising α-glucosidase inhibitors. The former are analogs of DNJ with an improved α-glucosidase inhibitory profile than that of DNJ. Boisson et al.Electric Literature of C6H13N

Referemce:
Piperidine – Wikipedia,
Piperidine | C5H11N – PubChem