(2S)-3-(5-fluoro-1H-indol-3-yl)-2-methylpropanoic acid | 1103518-32-6

• 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: (2S)-3-(5-fluoro-1H-indol-3-yl)-2-methylpropanoic acid
• 英文别名: (S)-3-(5-Fluoro-1H-indol-3-yl)-2-methylpropanoic acid
• CAS: 1103518-32-6
• 化学式: C₁₂H₁₂FNO₂
• 分子量: 221.231
• InChiKey: BLEQJARIPMGEMW-ZETCQYMHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  16
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  53.1
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (2S)-3-(5-fluoro-1H-indol-3-yl)-2-methylpropanoic acid 在 1-羟基苯并三唑 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 、 氨 作用下， 以 四氢呋喃 、 水 为溶剂， 反应 18.0h， 以87%的产率得到(2S)-3-(5-fluoro-1H-indol-3-yl)-2-methylpropanamide
  参考文献：
  名称：

  First Scale-Up Synthesis of WAY-262398, a Novel, Dual-Acting SSRI/5HT1a Antagonist

  摘要：

  An alternative synthesis of WAY-262398, 1, a novel, dual-acting SSRI/5-HT(1A) antagonist, has been developed. The target compound was initially synthesized as a part of diastereomeric mixture which was separated by chiral preparative HPLC. The new route was designed around intermediates suitable for chiral resolution and/or chiral reduction of a suitable intermediate. Both processes had to be employed to achieve the target optical purity.

  DOI：

  10.1021/op8002085
• 作为产物：
  描述：

  (2E)-3-(5-fluoro-1H-indol-3-yl)-2-methylacrylic acid 在 bis(norbornadiene)rhodium(l)tetrafluoroborate 、 (α,α)2,2'-bis(α-N,N-dimethylaminophenylmethyl)-(S,S)-1,1'-bis-[di(3,5-dimethyl-4-methoxyphenyl)-phosphino]ferrocene 、 氢气 作用下， 以 甲醇 为溶剂， 反应 15.0h， 以80%的产率得到(2S)-3-(5-fluoro-1H-indol-3-yl)-2-methylpropanoic acid
  参考文献：
  名称：

  First Scale-Up Synthesis of WAY-262398, a Novel, Dual-Acting SSRI/5HT1a Antagonist

  摘要：

  An alternative synthesis of WAY-262398, 1, a novel, dual-acting SSRI/5-HT(1A) antagonist, has been developed. The target compound was initially synthesized as a part of diastereomeric mixture which was separated by chiral preparative HPLC. The new route was designed around intermediates suitable for chiral resolution and/or chiral reduction of a suitable intermediate. Both processes had to be employed to achieve the target optical purity.

  DOI：

  10.1021/op8002085

文献信息

• FLUORINE CONTAINING COMPOUNDS AND METHODS OF USE THEREOF
  申请人：Ritter Tobias

  公开号：US20120095217A1

  公开（公告）日：2012-04-19

  Fluorinated compounds and methods of making fluorinated compounds are described herein.