3-噁-6-氮杂双环[3.1.0]己烷 | 5834-36-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 恶嗪烷类
• 中文名称: 3-噁-6-氮杂双环[3.1.0]己烷
• 英文名称: 3-oxa-6-azabicyclo[3.1.0]hexane
• 英文别名: 3-Oxa-6-aza-bicyclo<3.1.0>hexan
• CAS: 5834-36-6
• 化学式: C₄H₇NO
• mdl: MFCD19219235
• 分子量: 85.1057
• InChiKey: NGXORXSKEIVRPY-UHFFFAOYSA-N

物化性质

• 沸点：
  130.7±15.0 °C(Predicted)
• 密度：
  1.141±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -0.7
• 重原子数：
  6
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  31.2
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  2-吡啶甲酸 、 3-噁-6-氮杂双环[3.1.0]己烷 在 4-二甲氨基吡啶 、 N,N'-二异丙基碳二亚胺 作用下， 以 二氯甲烷 为溶剂， 反应 16.0h， 生成 3-oxa-6-azabicyclo[3.1.0]hexan-6-yl(pyridin-2-yl)methanone
  参考文献：
  名称：

  Enantioselective fluoride ring opening of aziridines enabled by cooperative Lewis acid catalysis

  摘要：

  The enantioselective ring opening of aziridines using a latent source of HF is described. A combination of two Lewis acids, (salen)Co and an achiral Ti(IV) cocatalyst, provided optimal reactivity and enantioselectivity for the trans beta-fluoroamine product. The use of a chelating aziridine protecting group was crucial. Acyclic and cyclic meso N-picolinamide aziridines underwent fluoride ring opening in up to 84% ee, and the kinetic resolution of a piperidine-derived aziridine was performed with k(rel)=6.6. The picolinamide group may be readily removed without epimerization of the fluoroamine. Preliminary studies revealed a bimetallic mechanism wherein the chiral (salen)Co catalyst delivers the nucleophile and the Ti(IV) cocatalyst activates the aziridine. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2013.01.062
• 作为产物：
  描述：

  反式-4-氨基-3-羟基四氢呋喃 在 硫酸 、 sodium hydroxide 作用下， 以 水 为溶剂， 反应 11.0h， 生成 3-噁-6-氮杂双环[3.1.0]己烷
  参考文献：
  名称：

  Enantioselective ring-opening of aziridines

  摘要：

  一种制备环氧丙烷和亲核试剂的亲核加成产物的方法，该方法包括在双芳基磷酸催化剂存在下处理环氧丙烷和亲核试剂。

  公开号：

  US20090030212A1

文献信息

• Aziridines. XIV. 3-Oxa-6-azabicyclo[3.1.0]hexane¹
  作者：Paul E. Fanta、Edward N. Walsh

  DOI：10.1021/jo01339a011

  日期：1966.1
• Enantioselective fluoride ring opening of aziridines enabled by cooperative Lewis acid catalysis
  作者：Julia A. Kalow、Abigail G. Doyle

  DOI：10.1016/j.tet.2013.01.062

  日期：2013.7

  The enantioselective ring opening of aziridines using a latent source of HF is described. A combination of two Lewis acids, (salen)Co and an achiral Ti(IV) cocatalyst, provided optimal reactivity and enantioselectivity for the trans beta-fluoroamine product. The use of a chelating aziridine protecting group was crucial. Acyclic and cyclic meso N-picolinamide aziridines underwent fluoride ring opening in up to 84% ee, and the kinetic resolution of a piperidine-derived aziridine was performed with k(rel)=6.6. The picolinamide group may be readily removed without epimerization of the fluoroamine. Preliminary studies revealed a bimetallic mechanism wherein the chiral (salen)Co catalyst delivers the nucleophile and the Ti(IV) cocatalyst activates the aziridine. (C) 2013 Elsevier Ltd. All rights reserved.
• Enantioselective ring-opening of aziridines
  申请人：Antilla Jon C.

  公开号：US20090030212A1

  公开（公告）日：2009-01-29

  A process for the preparation of a nucleophilic addition product of an aziridine and a nucleophile, the process comprising treating the arizidine with the nucleophile in the presence of a biaryl phosphoric acid catalyst

  一种制备环氧丙烷和亲核试剂的亲核加成产物的方法，该方法包括在双芳基磷酸催化剂存在下处理环氧丙烷和亲核试剂。