(1S)-N-[(1R)-phenylethyl]-1-phenyl-2-(piperidin-1-yl)ethanamine

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: (1S)-N-[(1R)-phenylethyl]-1-phenyl-2-(piperidin-1-yl)ethanamine
• 英文别名: (1S)-1-phenyl-N-[(1R)-1-phenylethyl]-2-piperidin-1-ylethanamine
• 化学式: C₂₁H₂₈N₂
• 分子量: 308.467
• InChiKey: PBLZSAGWKATFIV-WIYYLYMNSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.1
• 重原子数：
  23
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  15.3
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  (S)-(+)-扁桃酸 在 lithium aluminium tetrahydride 、 1-羟基苯并三唑 、 三乙胺 、 N,N'-二环己基碳二亚胺 、 copper dichloride 作用下， 以 四氢呋喃 、 乙醚 、 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 57.0h， 生成 (1S)-N-[(1R)-phenylethyl]-1-phenyl-2-(piperidin-1-yl)ethanamine
  参考文献：
  名称：

  Synthesis of chiral non-racemic 1,2-diamines from O-acetyl mandelic acid: application in enantioselective deprotonation of epoxides and diethylzinc addition to aldehydes

  摘要：

  A variety of 1,2-diamines were synthesized from readily available O-acetyl mandelic acid. These diamines were used in the synthesis of key intermediates for the preparation of (-)-utenone A and carbovir involving enantioselective deprotonation of epoxides, The addition of Et2Zn catalysed by some of these diamines was also studied and although ees were not high, some interesting observations were made in the outcome of the stereochemistry of the product. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(02)00376-9
• 作为试剂：
  描述：

  diethylzinc 、 甲氧基-三氟甲基苯 、 4-氯苯甲醛 在 (1S)-N-[(1R)-phenylethyl]-1-phenyl-2-(piperidin-1-yl)ethanamine 、 4-二甲氨基吡啶 、 三乙胺 作用下， 以 正己烷 、 环己烷 、 二氯甲烷 为溶剂， 反应 20.0h， 生成 (R)-3,3,3-Trifluoro-2-methoxy-2-phenyl-propionic acid (R)-1-(4-chloro-phenyl)-propyl ester 、 (R)-3,3,3-Trifluoro-2-methoxy-2-phenyl-propionic acid (S)-1-(4-chloro-phenyl)-propyl ester
  参考文献：
  名称：

  Synthesis of chiral non-racemic 1,2-diamines from O-acetyl mandelic acid: application in enantioselective deprotonation of epoxides and diethylzinc addition to aldehydes

  摘要：

  A variety of 1,2-diamines were synthesized from readily available O-acetyl mandelic acid. These diamines were used in the synthesis of key intermediates for the preparation of (-)-utenone A and carbovir involving enantioselective deprotonation of epoxides, The addition of Et2Zn catalysed by some of these diamines was also studied and although ees were not high, some interesting observations were made in the outcome of the stereochemistry of the product. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(02)00376-9

文献信息

• An Efficient Synthesis of Chiral Nonracemic Diamines: Application in Asymmetric Synthesis
  作者：Parthasarathy Saravanan、Vinod K Singh

  DOI：10.1016/s0040-4039(97)10578-0

  日期：1998.1

  A variety of chiral diamines have been synthesized from optically active mandelic acid in an efficient manner. The chiral nonracemic lithium amide base derived from one of the diamines has been used in formal asymmetric synthesis of natural products such as (−)-utenone A and (−)-carbovir. © 1997 Elsevier Science Ltd. All rights reserved.

  已经从旋光的扁桃酸中有效地合成了各种手性二胺。衍生自一种二胺的手性非外消旋锂酰胺碱已用于天然产物如（-）-泛酮A和（-）-carbovir的形式不对称合成。©1997 Elsevier ScienceLtd。保留所有权利。
• Synthesis of chiral non-racemic 1,2-diamines from O-acetyl mandelic acid: application in enantioselective deprotonation of epoxides and diethylzinc addition to aldehydes
  作者：P Saravanan、Alakesh Bisai、S Baktharaman、M Chandrasekhar、Vinod K Singh

  DOI：10.1016/s0040-4020(02)00376-9

  日期：2002.6

  A variety of 1,2-diamines were synthesized from readily available O-acetyl mandelic acid. These diamines were used in the synthesis of key intermediates for the preparation of (-)-utenone A and carbovir involving enantioselective deprotonation of epoxides, The addition of Et2Zn catalysed by some of these diamines was also studied and although ees were not high, some interesting observations were made in the outcome of the stereochemistry of the product. (C) 2002 Elsevier Science Ltd. All rights reserved.