(S)-2-(anilinomethyl)indoline | 305827-31-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吲哚及其衍生物
• 英文名称: (S)-2-(anilinomethyl)indoline
• 英文别名: N-[[(2S)-2,3-dihydro-1H-indol-2-yl]methyl]aniline
• CAS: 305827-31-0
• 化学式: C₁₅H₁₆N₂
• 分子量: 224.305
• InChiKey: SRKQVLAOEOLLDZ-AWEZNQCLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  17
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  24.1
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (S)-2-(anilinomethyl)indoline 、 三(二甲胺基)膦 以 甲苯 为溶剂， 反应 120.0h， 以90%的产率得到(2Sp,5Sc)-2-dimethylamino-3-phenyl-1,3-diaza-2-phosphabenzo[7,8]bicyclo[3.3.0]octane
  参考文献：
  名称：

  New P-stereogenic triaminophosphines and their derivatives: synthesis, structure, conformational study, and application as chiral ligands

  摘要：

  The synthesis, structural, and conformational studies of new P-chiral triaminophosphines, which feature an indolidine and a 1,2,3,4-tetrahydroquinolidine pattern, respectively, are reported. These compounds can feature very different 3D-structures, although they both could be seen a priori as close derivatives of the previously reported 3-phenyl-1,3-diaza-2-phosphabicyclo[3.3.0]octane. The consequences for the use of such compounds and their derivatives in asymmetric metal-catalysis are discussed on the basis of preliminary results in asymmetric cobalt-catalyzed [6+2] cycloaddition. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2010.03.013
• 作为产物：
  描述：

  N-叔丁氧羰基-L-吲哚啉-2-甲酸 在 N-甲基吗啉 、 lithium aluminium tetrahydride 、 三氟乙酸 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 68.25h， 生成 (S)-2-(anilinomethyl)indoline
  参考文献：
  名称：

  Catalytic asymmetric borane reduction of prochiral ketones by the use of diazaborolidine catalysts prepared from chiral β-diamines

  摘要：

  The catalytic asymmetric borane reduction of prochiral ketones was examined in the presence of chiral diazaborolidine catalysts prepared in situ from chiral P-diamines and borane. Chiral secondary alcohols were obtained with modest to high enantiomeric excesses (up to 92% ee) using (S)-2-[(4-trifluoromethyl)anilinomethyl]indoline 2f. (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(00)00414-6

文献信息

• Catalytic Asymmetric Borane Reduction of Prochiral Ketones by the Use of Chiral<i>β</i>-Diamines
  作者：Masatoshi Asami、Shinsuke Sato、Hiroyasu Watanabe

  DOI：10.1246/cl.2000.990

  日期：2000.9

  The catalytic asymmetric borane reduction of prochiral ketones was examined in the presence of chiral β-diamines. Chiral secondary alcohols were obtained with modest to high enantiomeric excesses (up to 92% ee) using (S)-2-[(p-trifluoromethyl)anilinomethyl]indoline.

  在手性 β-二胺存在下检查了前手性酮的催化不对称硼烷还原。使用 (S)-2-[(p-三氟甲基) 苯胺甲基] 二氢吲哚获得了适度到高对映体过量（高达 92% ee）的手性仲醇。
• Catalytic asymmetric borane reduction of prochiral ketones by the use of diazaborolidine catalysts prepared from chiral β-diamines
  作者：Shinsuke Sato、Hiroyasu Watanabe、Masatoshi Asami

  DOI：10.1016/s0957-4166(00)00414-6

  日期：2000.11

  The catalytic asymmetric borane reduction of prochiral ketones was examined in the presence of chiral diazaborolidine catalysts prepared in situ from chiral P-diamines and borane. Chiral secondary alcohols were obtained with modest to high enantiomeric excesses (up to 92% ee) using (S)-2-[(4-trifluoromethyl)anilinomethyl]indoline 2f. (C) 2000 Elsevier Science Ltd. All rights reserved.
• New P-stereogenic triaminophosphines and their derivatives: synthesis, structure, conformational study, and application as chiral ligands
  作者：Nicolas Toselli、Remy Fortrie、David Martin、Gérard Buono

  DOI：10.1016/j.tetasy.2010.03.013

  日期：2010.5

  The synthesis, structural, and conformational studies of new P-chiral triaminophosphines, which feature an indolidine and a 1,2,3,4-tetrahydroquinolidine pattern, respectively, are reported. These compounds can feature very different 3D-structures, although they both could be seen a priori as close derivatives of the previously reported 3-phenyl-1,3-diaza-2-phosphabicyclo[3.3.0]octane. The consequences for the use of such compounds and their derivatives in asymmetric metal-catalysis are discussed on the basis of preliminary results in asymmetric cobalt-catalyzed [6+2] cycloaddition. (C) 2010 Elsevier Ltd. All rights reserved.