(1R,2S)-2-(methyl(prop-2-ynyl)amino)-1-phenylpropan-1-ol | 710307-09-8

• 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: (1R,2S)-2-(methyl(prop-2-ynyl)amino)-1-phenylpropan-1-ol
• 英文别名: (1R,2S)-2-[methyl(prop-2-ynyl)amino]-1-phenylpropan-1-ol
• CAS: 710307-09-8
• 化学式: C₁₃H₁₇NO
• 分子量: 203.284
• InChiKey: ALYVCRJVPZAKEO-AAEUAGOBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 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：
  23.5
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (1R,2S)-2-(methyl(prop-2-ynyl)amino)-1-phenylpropan-1-ol 在 氯化亚砜 、 sodium azide 作用下， 以 二氯甲烷 、 二甲基亚砜 为溶剂， 反应 2.0h， 生成 (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 、 3-溴丙炔 在 potassium carbonate 作用下， 以 乙腈 为溶剂， 以97%的产率得到(1R,2S)-2-(methyl(prop-2-ynyl)amino)-1-phenylpropan-1-ol
  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

• Mild Reaction Conditions for the Terminal Deuteration of Alkynes
  作者：Sean P. Bew、Glyn D. Hiatt-Gipson、Jenny. A. Lovell、Christophe Poullain

  DOI：10.1021/ol2029178

  日期：2012.1.20

  Routinely employed syntheses of terminally deuterated alkynes often utilize strong bases (i.e., LDA, n-BuLi, or Grignard reagents) or low (i.e., -78 degrees C) or elevated (i.e., 56 degrees C) reaction temperatures; furthermore many of these procedures afford average yields and in some cases less than optimum deuterium incorporation. Herein we report the application of alternative extremely mild reaction conditions that readily afford quantitative yields of terminally deuterated alkynes in a matter of minutes with exceptional isotope incorporation at ambient temperature.
• 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.