(S)-N-benzyl-1-[(S)-2,2-dimethyl-1,3-dioxolan-4-yl]-2-phenylethanamine | 1202649-46-4

• 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: (S)-N-benzyl-1-[(S)-2,2-dimethyl-1,3-dioxolan-4-yl]-2-phenylethanamine
• 英文别名: (1S)-N-benzyl-1-[(4S)-2,2-dimethyl-1,3-dioxolan-4-yl]-2-phenylethanamine
• CAS: 1202649-46-4
• 化学式: C₂₀H₂₅NO₂
• 分子量: 311.424
• InChiKey: OFMNWQVBUUOIJE-RBUKOAKNSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  23
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  30.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  二碳酸二叔丁酯 、 (S)-N-benzyl-1-[(S)-2,2-dimethyl-1,3-dioxolan-4-yl]-2-phenylethanamine 在 三乙胺 作用下， 以 甲醇 为溶剂， 反应 3.0h， 以96%的产率得到(S)-N-benzyl-N-tert-butoxycarbonyl-1-[(S)-2,2-dimethyl-1,3-dioxolan-4-yl]-2-phenylethanamine
  参考文献：
  名称：

  Expedient asymmetric synthesis of (2S,3S)-Boc-phenylalanine epoxide, a key intermediate for the synthesis of biologically active compounds

  摘要：

  The asymmetric synthesis of (2S,3S)-3-(tert-butoxycarbonyl)amino-1,2-epoxy-4-plienylbutane [(2S,3S)-Boc-phenylalanine epoxide] has been achieved in six steps and in 55% overall yield from the N-benzylimine derived from (R)-2,3-O-isopropylidene-glyceraldehyde. The required vic-aminodiol intermediate was obtained through a highly diastereoselective addition of benzylmagnesium chloride to the N-benzylimine in the presence of BF3 center dot OEt2 as an imine precomplexing agent. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2009.08.001
• 作为产物：
  描述：

  (2S)-2,3-O-isopropylideneglyceraldehyde N-benzylimine 、 苄基氯化镁 在 三氟化硼乙醚 、 碳酸氢钠 作用下， 以 乙醚 、 水 为溶剂， 反应 5.0h， 以72%的产率得到(S)-N-benzyl-1-[(S)-2,2-dimethyl-1,3-dioxolan-4-yl]-2-phenylethanamine
  参考文献：
  名称：

  Expedient asymmetric synthesis of (2S,3S)-Boc-phenylalanine epoxide, a key intermediate for the synthesis of biologically active compounds

  摘要：

  The asymmetric synthesis of (2S,3S)-3-(tert-butoxycarbonyl)amino-1,2-epoxy-4-plienylbutane [(2S,3S)-Boc-phenylalanine epoxide] has been achieved in six steps and in 55% overall yield from the N-benzylimine derived from (R)-2,3-O-isopropylidene-glyceraldehyde. The required vic-aminodiol intermediate was obtained through a highly diastereoselective addition of benzylmagnesium chloride to the N-benzylimine in the presence of BF3 center dot OEt2 as an imine precomplexing agent. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2009.08.001

文献信息

• Expedient asymmetric synthesis of (2S,3S)-Boc-phenylalanine epoxide, a key intermediate for the synthesis of biologically active compounds
  作者：Ramón Badorrey、María D. Díaz-de-Villegas、José A. Gálvez

  DOI：10.1016/j.tetasy.2009.08.001

  日期：2009.10

  The asymmetric synthesis of (2S,3S)-3-(tert-butoxycarbonyl)amino-1,2-epoxy-4-plienylbutane [(2S,3S)-Boc-phenylalanine epoxide] has been achieved in six steps and in 55% overall yield from the N-benzylimine derived from (R)-2,3-O-isopropylidene-glyceraldehyde. The required vic-aminodiol intermediate was obtained through a highly diastereoselective addition of benzylmagnesium chloride to the N-benzylimine in the presence of BF3 center dot OEt2 as an imine precomplexing agent. (C) 2009 Elsevier Ltd. All rights reserved.