2-diphenylhydroxymethyl-1-methylaziridine

• 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: 2-diphenylhydroxymethyl-1-methylaziridine
• 英文别名: [(2S)-1-methylaziridin-2-yl]-diphenylmethanol
• 化学式: C₁₆H₁₇NO
• 分子量: 239.317
• InChiKey: AJOMLSCKRPIGFH-MYJWUSKBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  18
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  23.2
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  二苯甲酮 、 在 仲丁基锂 、 鹰爪豆碱 、 乙醇 作用下， 以 四氢呋喃 、 环己烷 、 甲苯 、 二氯甲烷 为溶剂， 反应 29.0h， 生成 2-diphenylhydroxymethyl-1-methylaziridine
  参考文献：
  名称：

  The stereochemistry of aziridine borane lithiation: diastereoselectivity and enantioselectivity

  摘要：

  Lithiation of 1-methylaziridine borane, 1-(tert-butyldimethylsiloxyethyl)aziridine borane, or 1-(tert-butyldimethylsiloxyethyl)-2-methylaziridine borane occurs syn to the boron substituent, while lithiation of 1-(tert-butyldimethylsiloxyethyl)-2-trimethylstannylaziridine borane occurs anti to boron as well as silicon due to the steric effect of trimethylsilyl group (s-butyllithium was used in all cases). Kinetically controlled lithiation in the first three cases results from a combination of steric and electrostatic effects. Enantioselective lithiation occurs in the presence of (-)-sparteine, with product enantioselectivities near 70% ee. (C) 2003 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2003.09.035

文献信息

• The stereochemistry of aziridine borane lithiation: diastereoselectivity and enantioselectivity
  作者：E Vedejs、A.S Bhanu Prasad、J.T Kendall、J.S Russel

  DOI：10.1016/j.tet.2003.09.035

  日期：2003.12

  Lithiation of 1-methylaziridine borane, 1-(tert-butyldimethylsiloxyethyl)aziridine borane, or 1-(tert-butyldimethylsiloxyethyl)-2-methylaziridine borane occurs syn to the boron substituent, while lithiation of 1-(tert-butyldimethylsiloxyethyl)-2-trimethylstannylaziridine borane occurs anti to boron as well as silicon due to the steric effect of trimethylsilyl group (s-butyllithium was used in all cases). Kinetically controlled lithiation in the first three cases results from a combination of steric and electrostatic effects. Enantioselective lithiation occurs in the presence of (-)-sparteine, with product enantioselectivities near 70% ee. (C) 2003 Elsevier Ltd. All rights reserved.