2-((S)-indolin-2-yl)propan-2-ol | 200644-42-4

• 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: 2-((S)-indolin-2-yl)propan-2-ol
• 英文别名: 2-[(2S)-2,3-dihydro-1H-indol-2-yl]propan-2-ol
• CAS: 200644-42-4
• 化学式: C₁₁H₁₅NO
• 分子量: 177.246
• InChiKey: WVZRABNYOXMCOE-JTQLQIEISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  13
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.45
• 拓扑面积：
  32.3
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  2-((S)-indolin-2-yl)propan-2-ol 在 sodium hydride 、 lithium diisopropyl amide 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 反应 6.0h， 生成
  参考文献：
  名称：

  Synthesis of two (S)-indoline-based chiral auxiliaries and their use in diastereoselective alkylation reactions

  摘要：

  Two chiral auxiliaries, 2-[(S)-indolin-2-yl]propan-2-ol 1a and (S)-2-(2-methoxypropan-2-yl)indoline 1b, were synthesised from enantiomerically pure (S)-indoline-2-carboxylic acid 3. High diastereoselectivities in alkylations of enolates of the propanoylamides derived from the two auxiliaries are presented. Surprisingly, both auxiliaries induced the same selectivity at the newly created stereogenic centre. The benzyl bromide and n-butyl iodide alkylation reactions showed diastereomeric ratios that were moderate (81:19) to very good (96:4) and with very good yields (86-98%). When LiCl was used as an enolate coordinating agent, in the benzylation of the enolate from propanoylated auxiliary la, a very high crude diastereomeric ratio was obtained (99.7:0.3). (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2006.07.002
• 作为产物：
  描述：

  methyl (S)-N-(tert-butoxycarbonyl)indoline-2-carboxylate 在 异丙基氯化镁 、 三氟乙酸 作用下， 以 四氢呋喃 、 乙醚 、 二氯甲烷 为溶剂， 反应 5.25h， 生成 2-((S)-indolin-2-yl)propan-2-ol
  参考文献：
  名称：

  2,2,3-三取代的四氢喹啉的立体定向合成：在苯扎他汀E和天然维霉素的总合成中的应用

  摘要：

  已经开发出一种有效的合成2,2,3-三取代的四氢喹啉的方法，该方法涉及三苯基膦-CCl 4介导的α，α-二取代的二氢吲哚-2-甲醇15至2,2,3-三取代的立体定向重排。四氢喹啉26。通过将非对映选择性的格利雅（Grignard）加到2-acylindoline 13上可以很容易地制备重排前体15。利用该方法完成了（+）-苯扎他汀E（1）和天然维他霉素（2a）的总合成。这种重排反应可能为苯扎他汀家族的生物遗传途径提供一些化学先例。

  DOI：

  10.1016/j.tet.2004.12.041

文献信息

• On the origins of enantioselectivity in oxazaborolidine mediated carbonyl reductions
  作者：Graham B Jones、Steven B Heaton、Brant J Chapman、Mustafa Guzel

  DOI：10.1016/s0957-4166(97)00497-7

  日期：1997.11

  A series of tricyclic oxazaborolidine catalysts have been prepared from readily available (S)-indoline-2-carboxylic acid. In each case, an arene chromium(O) carbonyl group was introduced on one face of the catalyst. Results obtained in the borane mediated reduction of ketones highlight the stereodirective importance of the alpha, alpha-appendages in the catalyst architecture. (C) 1997 Published by Elsevier Science Ltd.
• Stereospecific Construction of Contiguous Quaternary and Tertiary Stereocenters by Rearrangement from Indoline-2-methanol to 2,2,3-Trisubstituted Tetrahydroquinoline: Application to an Efficient Total Synthesis of Natural Virantmycin
  作者：Mayuko Ori、Narihiro Toda、Kazuko Takami、Keiko Tago、Hiroshi Kogen

  DOI：10.1002/anie.200351069

  日期：2003.6.6
• Stereospecific synthesis of 2,2,3-trisubstituted tetrahydroquinolines: application to the total syntheses of benzastatin E and natural virantmycin
  作者：Mayuko Ori、Narihiro Toda、Kazuko Takami、Keiko Tago、Hiroshi Kogen

  DOI：10.1016/j.tet.2004.12.041

  日期：2005.2

  for the synthesis of 2,2,3-trisubstituted tetrahydroquinolines has been developed, which involves the triphenylphosphine–CCl4-mediated stereospecific rearrangement of α,α-disubstituted indoline-2-methanols 15 to 2,2,3-trisubstituted tetrahydroquinolines 26. The rearrangement precursors 15 are readily prepared by the diastereoselective Grignard addition to 2-acylindolines 13. The total syntheses of (+)-benzastatin

  已经开发出一种有效的合成2,2,3-三取代的四氢喹啉的方法，该方法涉及三苯基膦-CCl 4介导的α，α-二取代的二氢吲哚-2-甲醇15至2,2,3-三取代的立体定向重排。四氢喹啉26。通过将非对映选择性的格利雅（Grignard）加到2-acylindoline 13上可以很容易地制备重排前体15。利用该方法完成了（+）-苯扎他汀E（1）和天然维他霉素（2a）的总合成。这种重排反应可能为苯扎他汀家族的生物遗传途径提供一些化学先例。
• Synthesis of two (S)-indoline-based chiral auxiliaries and their use in diastereoselective alkylation reactions
  作者：Fredrik Andersson、Erik Hedenström

  DOI：10.1016/j.tetasy.2006.07.002

  日期：2006.8

  Two chiral auxiliaries, 2-[(S)-indolin-2-yl]propan-2-ol 1a and (S)-2-(2-methoxypropan-2-yl)indoline 1b, were synthesised from enantiomerically pure (S)-indoline-2-carboxylic acid 3. High diastereoselectivities in alkylations of enolates of the propanoylamides derived from the two auxiliaries are presented. Surprisingly, both auxiliaries induced the same selectivity at the newly created stereogenic centre. The benzyl bromide and n-butyl iodide alkylation reactions showed diastereomeric ratios that were moderate (81:19) to very good (96:4) and with very good yields (86-98%). When LiCl was used as an enolate coordinating agent, in the benzylation of the enolate from propanoylated auxiliary la, a very high crude diastereomeric ratio was obtained (99.7:0.3). (c) 2006 Elsevier Ltd. All rights reserved.