[2R-(2S)]-1-benzyloxycarbonyl-2-(2,3-dihydroxypropyl)piperidine | 190383-53-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: [2R-(2S)]-1-benzyloxycarbonyl-2-(2,3-dihydroxypropyl)piperidine
• 英文别名: benzyl (2R)-2-[(2S)-2,3-dihydroxypropyl]piperidine-1-carboxylate
• CAS: 190383-53-0
• 化学式: C₁₆H₂₃NO₄
• 分子量: 293.363
• InChiKey: OSWVPYDGCQQGTR-CABCVRRESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  21
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.56
• 拓扑面积：
  70
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  [2R-(2S)]-1-benzyloxycarbonyl-2-(2,3-dihydroxypropyl)piperidine 在 palladium dihydroxide copper(I) bromide dimethylsulfide complex 、 氢气 作用下， 以 甲醇 为溶剂， 生成 (-)-halosaline
  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
• 作为产物：
  描述：

  (R)-1-benzyloxycarbonyl-2-(2-propenyl)piperidine 在 (8a,9R,8′′′a,9′′′R)-9,9′-[(2,5-diphenylpyrimidine-4,6-diyl)bis(oxy)]bis(6′-methoxy-10,11-dihydrocinchonan) potassium osmate(VI) 、 potassium carbonate 、 potassium hexacyanoferrate(III) 作用下， 以 水 、 叔丁醇 为溶剂， 反应 24.0h， 以70%的产率得到[2R-(2S)]-1-benzyloxycarbonyl-2-(2,3-dihydroxypropyl)piperidine
  参考文献：
  名称：

  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

  摘要：

  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.

  DOI：

  10.1021/jo991034w

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.
• 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.