N-pivaloyl-(R)-2-phenyl-(R)-3-phenylindoline | 1352451-34-3

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 二苯乙烯类
• 英文名称: N-pivaloyl-(R)-2-phenyl-(R)-3-phenylindoline
• 英文别名: 1-[(2R,3R)-2,3-diphenyl-2,3-dihydroindol-1-yl]-2,2-dimethylpropan-1-one
• CAS: 1352451-34-3
• 化学式: C₂₅H₂₅NO
• 分子量: 355.48
• InChiKey: KHAIPZOEPFGOJV-PKTZIBPZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.7
• 重原子数：
  27
• 可旋转键数：
  3
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.24
• 拓扑面积：
  20.3
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为产物：
  描述：

  1,2-diphenyl-2-(pivaloylamidophenyl)ethanol 在 盐酸 作用下， 以 1,4-二氧六环 、 水 为溶剂， 反应 1.0h， 以103 mg的产率得到N-pivaloyl-(R)-2-phenyl-(R)-3-phenylindoline
  参考文献：
  名称：

  Asymmetric Synthesis of trans-2,3-Disubstituted Indoline Derivatives

  摘要：

  A novel method for asymmetric synthesis of trans-2,3-disubstituted indolines has been developed. The strategy involves the (-)-sparteine-mediated electrophilic substitution of 2-benzyl N-pivaloylaniline with aromatic or alpha,beta-unsaturated aldehydes and subsequent intramolecular nucleophilic substitution. The simple protocol for two-step process can produce highly enantioenriched indolines 3a-o up to 98:2 er.

  DOI：

  10.1021/jo2023526

文献信息

• Mitsunobu cyclodehydration of N-pivaloyl-2-aminophenethyl alcohol for asymmetric synthesis of trans-2,3-disubstituted indolines
  作者：Kyoung Hee Kang、Yelim Kim、Chan Im、Yong Sun Park

  DOI：10.1016/j.tet.2013.01.063

  日期：2013.3

  Highly enantioenriched trans-2,3-disubstituted indolines have been prepared by Mitsunobu cyclodehydration of the amino alcohols obtained from (-)- or (+)-sparteine-mediated lithiation-substitution of ortho-alkyl substituted N-pivaloylanilines. Optimized cyclodehydration conditions are described, from which the combination of DEAD and PBu3 in CH3CN provides the best results. (C) 2013 Elsevier Ltd. All rights reserved.
• Asymmetric Synthesis of <i>trans</i>-2,3-Disubstituted Indoline Derivatives
  作者：Kyoung Hee Kang、Junghwan Do、Yong Sun Park

  DOI：10.1021/jo2023526

  日期：2012.1.6

  A novel method for asymmetric synthesis of trans-2,3-disubstituted indolines has been developed. The strategy involves the (-)-sparteine-mediated electrophilic substitution of 2-benzyl N-pivaloylaniline with aromatic or alpha,beta-unsaturated aldehydes and subsequent intramolecular nucleophilic substitution. The simple protocol for two-step process can produce highly enantioenriched indolines 3a-o up to 98:2 er.