(1S,2S)-N-methyl-1-phenyl-2-(1-pyrrolidinyl)-1-propanamine

• 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,2S)-N-methyl-1-phenyl-2-(1-pyrrolidinyl)-1-propanamine
• 英文别名: (1S,2S)-N-methyl-1-phenyl-2-pyrrolidin-1-ylpropan-1-amine
• 化学式: C₁₄H₂₂N₂
• 分子量: 218.342
• InChiKey: WQRPPOVTJXJKLU-GXTWGEPZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  16
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.57
• 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：

  去甲麻黄碱 在 盐酸 、 偶氮二甲酸二异丙酯 、 四丁基碘化铵 、 sodium carbonate 、 三乙胺 、 三苯基膦 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 129.5h， 生成 (1S,2S)-N-methyl-1-phenyl-2-(1-pyrrolidinyl)-1-propanamine
  参考文献：
  名称：

  Enantioselective rearrangement of a meso-cyclohexene oxide using norephedrine-derived chiral bases

  摘要：

  Using a chiral base from a norephedrine-derived diamine, the enantioselective rearrangement of a mesocyclohexene oxide can be performed in 94% yield and with 94% enantioselectivity. The enantioselectivity is lower (86% ee) with the diastereoisomeric chiral base. In order to prepare the diastereoisomeric chiral base, a potentially useful way of converting norephedrine into norpseudophedrine was developed. (C) 1999 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(99)00432-2
• 作为试剂：
  描述：

  (1SR,2RS,4RS,5SR)-4,5-bis(tert-butyldimethylsilyloxy)cyclohexene oxide 在 正丁基锂 、 (1S,2S)-N-methyl-1-phenyl-2-(1-pyrrolidinyl)-1-propanamine 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 反应 16.0h， 生成 (1R,4S,5R)-4,5-bis(tert-butyldimethylsilyloxy)cyclohex-2-en-1-ol 、 (1S,4R,5S)-4,5-bis(tert-butyldimethylsilyloxy)cyclohex-2-enol
  参考文献：
  名称：

  Enantioselective rearrangement of a meso-cyclohexene oxide using norephedrine-derived chiral bases

  摘要：

  Using a chiral base from a norephedrine-derived diamine, the enantioselective rearrangement of a mesocyclohexene oxide can be performed in 94% yield and with 94% enantioselectivity. The enantioselectivity is lower (86% ee) with the diastereoisomeric chiral base. In order to prepare the diastereoisomeric chiral base, a potentially useful way of converting norephedrine into norpseudophedrine was developed. (C) 1999 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(99)00432-2

文献信息

• Enantioselective rearrangement of a meso-cyclohexene oxide using norephedrine-derived chiral bases
  作者：Bob Colman、Simon E de Sousa、Peter O'Brien、Timothy D Towers、Will Watson

  DOI：10.1016/s0957-4166(99)00432-2

  日期：1999.10

  Using a chiral base from a norephedrine-derived diamine, the enantioselective rearrangement of a mesocyclohexene oxide can be performed in 94% yield and with 94% enantioselectivity. The enantioselectivity is lower (86% ee) with the diastereoisomeric chiral base. In order to prepare the diastereoisomeric chiral base, a potentially useful way of converting norephedrine into norpseudophedrine was developed. (C) 1999 Elsevier Science Ltd. All rights reserved.