1,1-dimethylethyl (1aRS,2RS,7SR,7aSR)-1a,2,7,7a-tetrahydronaphth[2,3-b]oxiren-2,7-imine-8-carboxylate | 512203-75-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 四氢化萘
• 英文名称: 1,1-dimethylethyl (1aRS,2RS,7SR,7aSR)-1a,2,7,7a-tetrahydronaphth[2,3-b]oxiren-2,7-imine-8-carboxylate
• 英文别名: tert-butyl (1S,8R,9R,11S)-10-oxa-12-azatetracyclo[6.3.1.02,7.09,11]dodeca-2,4,6-triene-12-carboxylate
• CAS: 512203-75-7
• 化学式: C₁₅H₁₇NO₃
• 分子量: 259.305
• InChiKey: RXVPTUXJYIQEED-MPZDIEGVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  19
• 可旋转键数：
  2
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.53
• 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 (1aRS,2RS,7SR,7aSR)-1a,2,7,7a-tetrahydronaphth[2,3-b]oxiren-2,7-imine-8-carboxylate 在 四甲基乙二胺 作用下， 以 乙醚 、 Petroleum ether 为溶剂， 反应 6.0h， 以65%的产率得到1,1-dimethylethyl [3-(1-methylethyl)nathphalen-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：

  1,4-二氢-1,4-表亚氨基萘-9-羧酸叔丁酯 在 丙酮 、 四丁基铵亚硫酸酯 Oxone 、 edetate disodium 、 碳酸氢钠 作用下， 以 二氯甲烷 、 水 为溶剂， 反应 72.0h， 以80%的产率得到1,1-dimethylethyl (1aRS,2RS,7SR,7aSR)-1a,2,7,7a-tetrahydronaphth[2,3-b]oxiren-2,7-imine-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

• Enantioselective Alkylative Double Ring Opening of Epoxides: Synthesis of Enantioenriched Unsaturated Diols and Amino Alcohols
  作者：David M. Hodgson、Christopher R. Maxwell、Timothy J. Miles、Edyta Paruch、Matthew A. H. Stent、Ian R. Matthews、Francis X. Wilson、Jason Witherington

  DOI：10.1002/1521-3773(20021115)41:22<4313::aid-anie4313>3.0.co;2-b

  日期：2002.11.15
• 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.