1-phenyl-2-tosyl-2,3,9,9a-tetrahydro-1H-imidazo[1,5-a]indole | 1385016-04-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 1-phenyl-2-tosyl-2,3,9,9a-tetrahydro-1H-imidazo[1,5-a]indole
• 英文别名: 2-(4-Methylphenyl)sulfonyl-3-phenyl-1,3,3a,4-tetrahydroimidazo[1,5-a]indole；2-(4-methylphenyl)sulfonyl-3-phenyl-1,3,3a,4-tetrahydroimidazo[1,5-a]indole
• CAS: 1385016-04-5
• 化学式: C₂₃H₂₂N₂O₂S
• 分子量: 390.506
• InChiKey: WJPHQAAFSYJWCY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.8
• 重原子数：
  28
• 可旋转键数：
  3
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  49
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  1-甲酸基吲哚啉 在 lithium aluminium tetrahydride 、 叔丁基锂 、 triethyloxonium fluoroborate 作用下， 以 四氢呋喃 、 1,2-二氯乙烷 、 正戊烷 为溶剂， 反应 40.75h， 生成 1-phenyl-2-tosyl-2,3,9,9a-tetrahydro-1H-imidazo[1,5-a]indole
  参考文献：
  名称：

  Nucleophilic addition of regioselectively lithiated indoline with aldimines for the syntheses of 2- and 7-indolinyl methanamine derivatives

  摘要：

  Indolines bearing different N-protecting groups (N-Tbf and N-Boc) were deprotonated regioselectively at C-2 (sp(3) hybridized ortho-H) and C-7 (sp(2) hybridized para-H) of the indoline ring, respectively. The generated organolithium intermediates reacted with aldimines to give the desired products in good yields with excellent anti-diastereoselectivities (>99:1). The produced N-Ts-(1-Tbf-indolin-2-yl)methanamine was facilely transformed to a fused heterocyclic compound. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2012.05.119

文献信息

• Nucleophilic addition of regioselectively lithiated indoline with aldimines for the syntheses of 2- and 7-indolinyl methanamine derivatives
  作者：Liang Cheng、Li Liu、Chuan Li、Han Jia、Dong Wang、Yong-Jun Chen

  DOI：10.1016/j.tetlet.2012.05.119

  日期：2012.8

  Indolines bearing different N-protecting groups (N-Tbf and N-Boc) were deprotonated regioselectively at C-2 (sp(3) hybridized ortho-H) and C-7 (sp(2) hybridized para-H) of the indoline ring, respectively. The generated organolithium intermediates reacted with aldimines to give the desired products in good yields with excellent anti-diastereoselectivities (>99:1). The produced N-Ts-(1-Tbf-indolin-2-yl)methanamine was facilely transformed to a fused heterocyclic compound. (C) 2012 Elsevier Ltd. All rights reserved.