2,3-dibenzyl-3-azabicyclo[3.1.0]hexan-1-ol | 192655-87-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 哌啶类
• 英文名称: 2,3-dibenzyl-3-azabicyclo[3.1.0]hexan-1-ol
• 英文别名: (2S)-2,3-dibenzyl-3-azabicyclo[3.1.0]hexan-1-ol
• CAS: 192655-87-1
• 化学式: C₁₉H₂₁NO
• 分子量: 279.382
• InChiKey: PNLCSYVRNOGHQY-XBMUEBEBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  21
• 可旋转键数：
  4
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.37
• 拓扑面积：
  23.5
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  2,3-dibenzyl-3-azabicyclo[3.1.0]hexan-1-ol 在 氧气 、 silica gel 作用下， 生成
  参考文献：
  名称：

  Substituted azabicyclo[3.1.0]hexan-1-ols from aspartic and glutamic acid derivatives via titanium-mediated cyclopropanation

  摘要：

  The Kulinkovich cyclopropanation reaction has been used to synthesize azabicyclo[3.1.0]hexanols from amino acid derivatives containing two ester moieties. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2008.08.114
• 作为产物：
  描述：

  N-烯丙基-N-苄基苯丙氨酸甲酯 在 titanium(IV) isopropylate 、 异丙基氯化镁 、 碳酸氢钠 作用下， 生成 2,3-dibenzyl-3-azabicyclo[3.1.0]hexan-1-ol
  参考文献：
  名称：

  Efficient and Practical Method for Synthesizing N-Heterocyclic Compounds Using Intramolecular Nucleophilic Acyl Substitution Reactions Mediated by Ti(O-i-Pr)₄/2i-PrMgX Reagent. Synthesis of Quinolones, Pyrroles, Indoles, and Optically Active N-Heterocycles Including Allopumiliotoxin Alkaloid 267A

  摘要：

  Treatment of N-(2- or 3-alkynyl)amino esters with a low-valent titanium reagent diisopropoxy(eta(2)-propene)titanium (1), generated in situ by the reaction of Ti(O-i-Pr)(4) and 2i-PrMgCl, resulted in an intramolecular nucleophilic acyl substitution (INAS) reaction to afford alpha-alkylidene-pyrrolidinones or -piperidinones. Thus, treatment of N-propargyl-anthranilates 5, -indole-2-carboxylates 10, or -pyrrole-2-carboxylates 13 with 1 gave 4-quinolones 7, [1,2-a]indoles, or [1,2-a]pyrroles, respectively. Similarly, N-alkynylated alpha- or beta-amino esters 14 or 15 with 1 afforded N-heterocycles 18 or 19. In the reaction of N-(2- or 3-alkenyl)amino esters with 1, the resulting INAS product underwent intramolecular carbonyl addition (ICA) reaction to afford the N-heterocyclic compounds having a cyclopropanol moiety in good to excellent yields. Thus, the treatment of N-alkenyl-anthranilate 4a, -indole-2-carboxylates 8 and 9, or -pyrrole-2-carboxylates 11 and 12 with 1 gave the corresponding quinoline derivative 6a, [1,2-a]indoles, or [1,2-a]pyrroles, respectively. The optically active N-heterocyclic compounds 20 and 21 were obtained from N-alkenylated alpha- or beta-amino esters 16 or 17. A highly efficient total synthesis of allopumiliotoxin alkaloid 267A has also been accomplished. Thus, the N-propargyl-2[(1-hydroxy-1-methoxycarbonyl)ethyl]pyrrolidine 24 (from L-proline in six steps) reacted with 1 to afford the corresponding indolidinone 25 in 67% yield, which has previously been converted to allopumiliotoxin 267A.

  DOI：

  10.1021/ja970810j