2-((S)-1-benzylindolin-2-yl)propan-2-ol | 912807-49-9

• 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)-1-benzylindolin-2-yl)propan-2-ol
• 英文别名: 2-[(2S)-1-benzyl-2,3-dihydroindol-2-yl]propan-2-ol
• CAS: 912807-49-9
• 化学式: C₁₈H₂₁NO
• 分子量: 267.371
• InChiKey: SFQPUMFBHJQNMW-KRWDZBQOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  20
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.33
• 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-((S)-1-benzylindolin-2-yl)propan-2-ol 在 palladium on activated charcoal 氢气 、 lithium diisopropyl amide 作用下， 以 四氢呋喃 、 乙醇 、 正己烷 为溶剂， 75.0 ℃ 、101.33 kPa 条件下， 反应 34.5h， 生成 (2R)-1-[(2S)-2-(2-hydroxypropan-2-yl)-2,3-dihydroindol-1-yl]-2-methylhexan-1-one
  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：

  (S)-吲哚啉-2-羧酸 在 氯化亚砜 、 potassium carbonate 、 三乙胺 作用下， 以 乙醚 、 甲苯 为溶剂， 反应 11.0h， 生成 2-((S)-1-benzylindolin-2-yl)propan-2-ol
  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

文献信息

• 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.