((1S,2R)-2-Chloro-1-methyl-2-phenyl-ethyl)-methyl-prop-2-ynyl-amine | 764647-99-6

• 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: ((1S,2R)-2-Chloro-1-methyl-2-phenyl-ethyl)-methyl-prop-2-ynyl-amine
• 英文别名: (1R,2S)-1-chloro-N-methyl-1-phenyl-N-prop-2-ynylpropan-2-amine
• CAS: 764647-99-6
• 化学式: C₁₃H₁₆ClN
• 分子量: 221.73
• InChiKey: NPIOAIGNRGQVBB-AAEUAGOBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  15
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  3.2
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  ((1S,2R)-2-Chloro-1-methyl-2-phenyl-ethyl)-methyl-prop-2-ynyl-amine 在 sodium azide 作用下， 以 二甲基亚砜 为溶剂， 反应 1.0h， 以71%的产率得到(6S,7R)-5,6-dimethyl-7-phenyl-4,5,6,7-tetrahydro-[1,2,3]triazolo[1,5,a]pyrazine
  参考文献：
  名称：

  Expeditive synthesis of homochiral fused tri- and tetrazoles–piperazines from β-amino alcohols

  摘要：

  N-Cyanomethyl and N-propargyl beta-amino alcohols are chlorinated with SOCl2 and treated with NaN3 in DMSO. A Substitution/cycloaddition process affords in good yields, with high diastereoselectivity and a regioselectivity depending on the substitution pattern of the starting amino alcohol, fused tri- and tetrazoles-pipci-azines. These heterocycles were further lithiated with n-BuLi at the benzylic position and reacted diastereoselectively with a range of electrophiles. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2004.03.092
• 作为产物：
  描述：

  麻黄碱 在 氯化亚砜 、 potassium carbonate 作用下， 以 二氯甲烷 、 乙腈 为溶剂， 反应 1.0h， 生成 ((1S,2R)-2-Chloro-1-methyl-2-phenyl-ethyl)-methyl-prop-2-ynyl-amine
  参考文献：
  名称：

  Expeditive synthesis of homochiral fused tri- and tetrazoles–piperazines from β-amino alcohols

  摘要：

  N-Cyanomethyl and N-propargyl beta-amino alcohols are chlorinated with SOCl2 and treated with NaN3 in DMSO. A Substitution/cycloaddition process affords in good yields, with high diastereoselectivity and a regioselectivity depending on the substitution pattern of the starting amino alcohol, fused tri- and tetrazoles-pipci-azines. These heterocycles were further lithiated with n-BuLi at the benzylic position and reacted diastereoselectively with a range of electrophiles. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2004.03.092

文献信息

• Expeditive synthesis of homochiral fused tri- and tetrazoles–piperazines from β-amino alcohols
  作者：François Couty、François Durrat、Damien Prim

  DOI：10.1016/j.tetlet.2004.03.092

  日期：2004.5

  N-Cyanomethyl and N-propargyl beta-amino alcohols are chlorinated with SOCl2 and treated with NaN3 in DMSO. A Substitution/cycloaddition process affords in good yields, with high diastereoselectivity and a regioselectivity depending on the substitution pattern of the starting amino alcohol, fused tri- and tetrazoles-pipci-azines. These heterocycles were further lithiated with n-BuLi at the benzylic position and reacted diastereoselectively with a range of electrophiles. (C) 2004 Elsevier Ltd. All rights reserved.