(+)-N-甲基石榴碱; (alphaS,2R)-alpha,1-二甲基-2-哌啶乙醇 | 41447-16-9

• 物质功能分类: 天然产物 - 生物碱
• 分子结构分类: 有机化合物 - 有机杂环化合物 - 哌啶类
• 中文名称: (+)-N-甲基石榴碱; (alphaS,2R)-alpha,1-二甲基-2-哌啶乙醇
• 中文别名: (ALPHAS,2R)-ALPHA,1-二甲基-2-哌啶乙醇
• 英文名称: (+)-1-(1-methyl-piperidin-2-yl)-propan-2-ol
• 英文别名: (+)-N-methylallosedridine；(+)-N-methyallosedridine；N-methylallosedridine；(S)-1-((R)-1-methyl-[2]piperidyl)-propan-2-ol；(2S)-1-[(2R)-1-Methylpiperidin-2-YL]propan-2-OL
• CAS: 41447-16-9
• 化学式: C₉H₁₉NO
• 分子量: 157.256
• InChiKey: JOHKCJPJMSCFBX-DTWKUNHWSA-N

物化性质

• 沸点：
  223.3±13.0 °C(Predicted)
• 密度：
  0.927±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.3
• 重原子数：
  11
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  23.5
• 氢给体数：
  1
• 氢受体数：
  2

安全信息

• 储存条件：
  存储条件：2-8℃，干燥，密闭。

反应信息

• 作为产物：
  描述：

  (R)-1-benzyloxycarbonyl-2-(2-propenyl)piperidine 在 lithium aluminium tetrahydride 、 hydroquinindine-2,5-diphenyl-4,6-pyrimidinediyl diether 作用下， 生成 (+)-N-甲基石榴碱; (alphaS,2R)-alpha,1-二甲基-2-哌啶乙醇
  参考文献：
  名称：

  A general entry to 2-(2-hydroxyalkyl)piperidines via iterative asymmetric dihydroxylation to cause enantiomeric enhancement

  摘要：

  Both enantiomers of 2-(2-propenyl)piperidine (1) (76-88% ee), prepared via the first AD of 5-hexenyl azide, underwent the second AD to provide all of the four stereoisomeric 2-(2-hydroxypropyl)-piperidines (2) with enantiomeric enhancement (>98% ee). An asymmetric synthesis, starting from 2,of several 2-(2-hydroxyalkyl)piperidine alkaloids are demonstrated. (C) 1997 Elsevier Science Ltd.

  DOI：

  10.1016/s0040-4039(97)00643-6

文献信息

• A New Synthesis of All Four Stereoisomers of 2-(2,3-Dihydroxypropyl)piperidine via Iterative Asymmetric Dihydroxylation To Cause Enantiomeric Enhancement. Application to Asymmetric Synthesis of Naturally Occurring Piperidine-Related Alkaloids
  作者：Hiroki Takahata、Minoru Kubota、Nobuo Ikota

  DOI：10.1021/jo991034w

  日期：1999.11.1

  Both enantiomers of 2-(2-propenyl)piperidine 1 (76-88% ee), prepared via the first asymmetric dihydroxylation (AD) of 5-hexenyl azide, underwent the second AD to provide all four of the stereoisomeric 2-(2,3-dihydroxypropyl)piperidines 2 with enantiomeric enhancement (>98% ee). An asymmetric synthesis, starting from 2, of several 2-(2-hydroxyalkyl)piperidine alkaloids [(-)-halosaline, (+)-N-methylallosedridine, (+)-8-ethylnorlobelol, (+)-sedridine, (+)-allosedridine, (-)-allosedridine, and (+)-N-methylsedridine] and the ant defense alkaloids [(+)-tetraponerine-3 (T-3), T-4, T-7, and T-8] is demonstrated.
• Short enantioselective synthesis of sedridines, ethylnorlobelols and coniine via reagent-based differentiation
  作者：Daniele Passarella、Alessio Barilli、Francesca Belinghieri、Paola Fassi、Sergio Riva、Alessandro Sacchetti、Alessandra Silvani、Bruno Danieli

  DOI：10.1016/j.tetasy.2005.05.032

  日期：2005.7

  The preparation of collections of structurally diverse small molecules is a useful tool for studying biology and medicine with chemistry. Herein, we demonstrate the versatility of the pure enantiomers of 2-(2-oxo-ethyl)-piperidine-1-carboxylic acid tertbutyl ester to prepare the biological active alkaloids sedridine, allosedridine, methylsedridine, methylallosedridine, ethylnorlobelol, and coniine in two steps and in a stereoselective way via a reagent-based differentiation. The described syntheses are a demonstration of the versatility of 2-(2-oxo-ethyl)-piperidine-1-carboxylic acid tert-butyl esters as chiral building blocks. (c) 2005 Elsevier Ltd. All rights reserved.
• Beyerman et al., Recueil des Travaux Chimiques des Pays-Bas, 1972, vol. 91, p. 1441,1445
  作者：Beyerman et al.

  DOI：——

  日期：——
• A general entry to 2-(2-hydroxyalkyl)piperidines via iterative asymmetric dihydroxylation to cause enantiomeric enhancement
  作者：Hiroki Takahata、Minoru Kubota、Takefumi Momose

  DOI：10.1016/s0040-4039(97)00643-6

  日期：1997.5

  Both enantiomers of 2-(2-propenyl)piperidine (1) (76-88% ee), prepared via the first AD of 5-hexenyl azide, underwent the second AD to provide all of the four stereoisomeric 2-(2-hydroxypropyl)-piperidines (2) with enantiomeric enhancement (>98% ee). An asymmetric synthesis, starting from 2,of several 2-(2-hydroxyalkyl)piperidine alkaloids are demonstrated. (C) 1997 Elsevier Science Ltd.