1,1-dimethylethyl (1RS,2RS,4SR,5SR)-8-aza-3-oxatricyclo[3.2.1.0^2,4]-6-octene-8-carboxylate | 702666-53-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 恶嗪烷类
• 英文名称: 1,1-dimethylethyl (1RS,2RS,4SR,5SR)-8-aza-3-oxatricyclo[3.2.1.0^2,4]-6-octene-8-carboxylate
• 英文别名: tert-butyl (1R,2R,4S,5S)-3-oxa-8-azatricyclo[3.2.1.02,4]oct-6-ene-8-carboxylate
• CAS: 702666-53-3
• 化学式: C₁₁H₁₅NO₃
• 分子量: 209.245
• InChiKey: AEXOQAIFBOPVCW-SPJNRGJMSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.9
• 重原子数：
  15
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.73
• 拓扑面积：
  42.1
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  异丙基锂 、 1,1-dimethylethyl (1RS,2RS,4SR,5SR)-8-aza-3-oxatricyclo[3.2.1.0^2,4]-6-octene-8-carboxylate 以 乙醚 、 Petroleum ether 为溶剂， 反应 1.0h， 以22%的产率得到1,1-dimethylethyl [(1S,2R)-2-hydroxy-3-(1-methylethyl)-3,5-cyclohexadien-1-yl]carbamate
  参考文献：
  名称：

  Organolithium-induced enantioselective alkylative double ring-opening of epoxides: synthesis of enantioenriched unsaturated amino alcohols

  摘要：

  The use of (-)-sparteine as an external chiral ligand in enantioselective organolithium-induced alkylative double ring-opening of dihydropyrrole epoxides and 7-azanorbornene-type epoxides gives unsaturated acyclic amino alcohols, and amino cyclohexenols in up to 87% ee. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2004.02.055
• 作为产物：
  描述：

  7-(tert-butoxycarbonyl)-7-azabicyclo[2.2.1]hepta-2,5-diene 在 溶剂黄146 过氧乙酸 、 sodium acetate 、 sodium carbonate 作用下， 反应 36.0h， 以77%的产率得到1,1-dimethylethyl (1RS,2RS,4SR,5SR)-8-aza-3-oxatricyclo[3.2.1.0^2,4]-6-octene-8-carboxylate
  参考文献：
  名称：

  Organolithium-induced enantioselective alkylative double ring-opening of epoxides: synthesis of enantioenriched unsaturated amino alcohols

  摘要：

  The use of (-)-sparteine as an external chiral ligand in enantioselective organolithium-induced alkylative double ring-opening of dihydropyrrole epoxides and 7-azanorbornene-type epoxides gives unsaturated acyclic amino alcohols, and amino cyclohexenols in up to 87% ee. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2004.02.055

文献信息

• Organolithium-induced enantioselective alkylative double ring-opening of epoxides: synthesis of enantioenriched unsaturated amino alcohols
  作者：David M. Hodgson、Christopher R. Maxwell、Timothy J. Miles、Edyta Paruch、Ian R. Matthews、Jason Witherington

  DOI：10.1016/j.tet.2004.02.055

  日期：2004.4

  The use of (-)-sparteine as an external chiral ligand in enantioselective organolithium-induced alkylative double ring-opening of dihydropyrrole epoxides and 7-azanorbornene-type epoxides gives unsaturated acyclic amino alcohols, and amino cyclohexenols in up to 87% ee. (C) 2004 Elsevier Ltd. All rights reserved.