3-methyl-r-2,t-3,c-5-triphenylpyrrolidine

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 二苯乙烯类
• 英文名称: 3-methyl-r-2,t-3,c-5-triphenylpyrrolidine
• 英文别名: (2R,3R,5R)-3-methyl-2,3,5-triphenylpyrrolidine
• 化学式: C₂₃H₂₃N
• 分子量: 313.442
• InChiKey: ROORESMCJJRGAW-DNVJHFABSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.3
• 重原子数：
  24
• 可旋转键数：
  3
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  12
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为产物：
  描述：

  二苄胺 在 六甲基磷酰三胺 、 N-氯代丁二酰亚胺 、 potassium tert-butylate 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 3.25h， 生成 3-methyl-r-2,t-3,c-5-triphenylpyrrolidine 、 3-methyl-r-2,c-3,c-5-triphenylpyrrolidine
  参考文献：
  名称：

  Preparation of 2-azaallyl anions and imines from N-chloroamines and their cycloaddition and allylation

  摘要：

  Exposure of N-chloroamines to (KOBu)-Bu-t or LDA, in the presence of PMDETA or HMPA, provides 2-azaallyl anions capable of pi 4s + pi 2s cycloaddition reactions with a range of olefins. Good yields were achieved with stabilised systems, however, they were more modest when accessing semi-stabilised 2-azaallyl anions. By modifying the reaction conditions, one-pot dehydrochlorination/allylation can also be achieved with a range of N-chloroamines. (C) 2010 Published by Elsevier Ltd.

  DOI：

  10.1016/j.tetlet.2010.11.142

文献信息

• Racemic 3-Methyl-<i>r</i>-2,<i>c</i>-3,<i>c</i>-5-triphenylpyrrolidine and 3-Methyl-<i>r</i>-2,<i>t</i>-3,<i>c</i>-5-triphenylpyrrolidine
  作者：L. B. Jerzykiewicz、T. Lis、J. Baran、D. Dziewońska-Baran

  DOI：10.1107/s0108270197018155

  日期：1998.6.15

  The 1,3-diphenyl-2-azaallyl anion adds almost quantitatively to 2-phenylpropene with retention of the conformation of the anion. Two racemic diastereoisomeric [3+2] cycloadducts, i.e. the corresponding pyrrolidines, are formed, in which both phenyl substituents derived from the anion are cis oriented. The structures of racemic 3-methyl-r-2,c-3,c-5-triphenylpyrrolidine, C23H23N, (I), and 3-methyl-r-2,t-3,c-5-triphenylpyrrolidine, C23H23N, (II), were determined by X-ray analysis. There is no intermolecular hydrogen bonding in either crystal.
• Preparation of 2-azaallyl anions and imines from N-chloroamines and their cycloaddition and allylation
  作者：Shveta Pandiancherri、David W. Lupton

  DOI：10.1016/j.tetlet.2010.11.142

  日期：2011.2

  Exposure of N-chloroamines to (KOBu)-Bu-t or LDA, in the presence of PMDETA or HMPA, provides 2-azaallyl anions capable of pi 4s + pi 2s cycloaddition reactions with a range of olefins. Good yields were achieved with stabilised systems, however, they were more modest when accessing semi-stabilised 2-azaallyl anions. By modifying the reaction conditions, one-pot dehydrochlorination/allylation can also be achieved with a range of N-chloroamines. (C) 2010 Published by Elsevier Ltd.