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

  左旋去甲麻黄碱 在 四丁基碘化铵 、 sodium carbonate 、 甲基磺酰氯 、 三乙胺 作用下， 以 四氢呋喃 、 水 为溶剂， 反应 48.0h， 生成 (1S,2R)-N-methyl-1-phenyl-2-(1-pyrrolidinyl)-1-propanamine
  参考文献：
  名称：

  一种新的去氧麻黄碱衍生的手性碱，用于环氧化物重排反应

  摘要：

  报道了（1 R，2 S）-去氧麻黄碱向新型手性二胺的转化（83％收率，简单的两步合成）及其在两个环氧化物重排反应中作为手性碱的用途。4，5-二取代的环己烯氧化物和4-氨基取代的环戊烯氧化物的重排产生＞ 90％ee的烯丙基醇。这些结果代表了迄今为止报道的此类底物的最高对映选择性水平。

  DOI：

  10.1016/s0040-4039(99)01740-2
• 作为试剂：
  描述：

  cyclohexene oxide 在 正丁基锂 、 (1S,2R)-N-methyl-1-phenyl-2-(1-pyrrolidinyl)-1-propanamine 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 生成 (R)-2-cyclohexen-1-ol 、 (S)-cyclohex-2-en-1-ol
  参考文献：
  名称：

  Investigation of site selectivity of the stereoselective deprotonation of cyclohexene oxide using kinetic resolution of isotopic enantiomers in natural abundance

  摘要：

  Stereo selective deprotonation of epoxides with lithium arnides can occur by abstraction of protons from more than one site. The site selectivity of the deprotonation of cyclohexene oxide by several chiral and achiral lithium amides has been investigated. H-2 NMR has been used to measure the relative abundances of the isotopomers of the epoxide containing one deuterium. An isotopic stereoisomer, with deuterium in the site undergoing abstraction, reacts slower than its enantiomer and other isotopomers having protium in the same site due to a kinetic isotope effect. This results in a kinetic resolution yielding a relative excess of the less reactive isotopic stereoisomer. Thus, the relative abundance of such an enantiomer increases when compared with those having protium at the site in question as the reaction proceeds. It can be concluded that deprotonation of cyclohexene oxide using some chiral- and non-chiral lithium amides occurs by beta syn-deprotonation. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2005.06.029

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.
• A new norephedrine-derived chiral base for epoxide rearrangement reactions
  作者：Simon E de Sousa、Peter O'Brien、H.Christian Steffens

  DOI：10.1016/s0040-4039(99)01740-2

  日期：1999.11

  The conversion of (1R,2S)-norephedrine into a novel chiral diamine (83% yield, simple two step synthesis) and its use as a chiral base in two epoxide rearrangement reactions is reported. Rearrangement of a 4,5-disubstituted cyclohexene oxide and of a 4-aminosubstituted cyclopentene oxide generated allylic alcohols of >90% ee. These results represent the highest levels of enantioselectivity reported

  报道了（1 R，2 S）-去氧麻黄碱向新型手性二胺的转化（83％收率，简单的两步合成）及其在两个环氧化物重排反应中作为手性碱的用途。4，5-二取代的环己烯氧化物和4-氨基取代的环戊烯氧化物的重排产生＞ 90％ee的烯丙基醇。这些结果代表了迄今为止报道的此类底物的最高对映选择性水平。