1-cyclohexyl-2-vinylaziridine

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: 1-cyclohexyl-2-vinylaziridine
• 英文别名: 1-N-cyclohexyl-2-vinylaziridine；N-cyclohexyl-vinylaziridine；1-Cyclohexyl-2-ethenylaziridine
• 化学式: C₁₀H₁₇N
• 分子量: 151.252
• InChiKey: VQVNGNCMAPFFAC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  11
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.8
• 拓扑面积：
  3
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  对甲氧基苯异氰酸酯 、 1-cyclohexyl-2-vinylaziridine 在 palladium diacetate 、 三苯基膦 作用下， 以 四氢呋喃 为溶剂， 反应 2.0h， 以88%的产率得到1-cyclohexyl-3-(4-methoxyphenyl)-4-vinyl-2H-imidazolidin-2-one
  参考文献：
  名称：

  Room Temperature Ring-Opening Cyclization Reactions of 2-Vinylaziridines with Isocyanates, Carbodiimides, and Isothiocyanates Catalyzed by [Pd(OAc)₂]/PPh₃

  摘要：

  2-Vinylaziridines undergo cycloaddition reactions with various heterocumulenes, in the presence of [Pd(OAc)(2)] and PPh3, at room temperature and 1 atm pressure, regioselectively affording five-membered ring products in moderate to high yields. The mixture of stereoisomers obtained by reactions employing cis-1-butyl-2-vinyl-3-methylaziridine as the reactant provides evidence for a mechanism involving a eta(3)-eta(1)-eta(3) interconversion of a (pi-allyl)palladium intermediate.

  DOI：

  10.1021/jo000608q

文献信息

• CeCl3 promoted asymmetric cycloaddition of isocyanates with 2-vinylaziridines
  作者：Chune Dong、Howard Alper

  DOI：10.1016/j.tetasy.2004.03.039

  日期：2004.5

  The enantioselective ring-opening cyclization of 2-vinylaziridines with various isocyanates, using Pd-2(dba)(3)(CHCl3)-C-., (S)-BINAP and CeCl3 as the catalytic system, afforded chiral imidazolidinones in 58-89% yield and in up to 83% ee. (C) 2004 Elsevier Ltd. All rights reserved.
• Coupling of vinyl aziridines and phenyl isocyanate
  作者：Kainan Zhang、Pramod R. Chopade、Janis Louie

  DOI：10.1016/j.tetlet.2008.04.121

  日期：2008.6

  Thermal coupling of vinyl aziridines and phenyl isocyanate was evaluated. Although oxazolidinone products were predominant, some reactions afforded a seven-membered ring heterocycle. When Ni/IMes was employed as a catalyst, a wider array of vinyl aziridines underwent coupling reactions. The Ni catalyzed reactions generally afforded vinyl imidazolidinones as major products. Published by Elsevier Ltd.
• Room Temperature Ring-Opening Cyclization Reactions of 2-Vinylaziridines with Isocyanates, Carbodiimides, and Isothiocyanates Catalyzed by [Pd(OAc)₂]/PPh₃
  作者：David C. D. Butler、Gyro A. Inman、Howard Alper

  DOI：10.1021/jo000608q

  日期：2000.9.1

  2-Vinylaziridines undergo cycloaddition reactions with various heterocumulenes, in the presence of [Pd(OAc)(2)] and PPh3, at room temperature and 1 atm pressure, regioselectively affording five-membered ring products in moderate to high yields. The mixture of stereoisomers obtained by reactions employing cis-1-butyl-2-vinyl-3-methylaziridine as the reactant provides evidence for a mechanism involving a eta(3)-eta(1)-eta(3) interconversion of a (pi-allyl)palladium intermediate.