6-fluoro-3-(1,2,3,6-tetrahydropyridin-4-yl)-1H-indole;hydrochloride | 501032-29-7

• 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: 6-fluoro-3-(1,2,3,6-tetrahydropyridin-4-yl)-1H-indole;hydrochloride
• CAS: 501032-29-7
• 化学式: C₁₃H₁₃FN₂*ClH
• 分子量: 252.719
• InChiKey: ZASHDDLFHIIADL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.11
• 重原子数：
  17
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.23
• 拓扑面积：
  27.8
• 氢给体数：
  3
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  6-fluoro-3-(1,2,3,6-tetrahydropyridin-4-yl)-1H-indole;hydrochloride 在 盐酸 、 sodium tetrahydroborate 作用下， 以 四氢呋喃 为溶剂， 反应 1.5h， 生成 6-氟-3-(哌啶-4-基)-1H-吲哚
  参考文献：
  名称：

  Novel chemoselective reduction of the tetrahydro-4-pyridyl versus indole moiety governed by electron donation: first X-ray evidence for indolopiperidyl–borane complexation

  摘要：

  A series of amino-borane complexes of structure type 2 are the key intermediates in the preparation of 3-(piperidyl) indole derivatives. The selective reduction of the tetrahydro-4-pyridyl double bond via 2 under strongly acidic conditions is feasible only when the pyridyl double bond is conjugated with electron rich substituents, such as indoles. This reduction methodology allows the presence of reducible and hydrogenolizable functional groups. An improved process to prepare 2 by treatment of the 3-(tetrahydro-4-pyridyl) indole derivatives with NaBH4 in THF under acidic conditions (AcOH or CF3COOH) is also described. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(02)01927-5

文献信息

• Novel chemoselective reduction of the tetrahydro-4-pyridyl versus indole moiety governed by electron donation: first X-ray evidence for indolopiperidyl–borane complexation
  作者：Alfio Borghese、Luc Antoine、Gregory Stephenson

  DOI：10.1016/s0040-4039(02)01927-5

  日期：2002.11

  A series of amino-borane complexes of structure type 2 are the key intermediates in the preparation of 3-(piperidyl) indole derivatives. The selective reduction of the tetrahydro-4-pyridyl double bond via 2 under strongly acidic conditions is feasible only when the pyridyl double bond is conjugated with electron rich substituents, such as indoles. This reduction methodology allows the presence of reducible and hydrogenolizable functional groups. An improved process to prepare 2 by treatment of the 3-(tetrahydro-4-pyridyl) indole derivatives with NaBH4 in THF under acidic conditions (AcOH or CF3COOH) is also described. (C) 2002 Elsevier Science Ltd. All rights reserved.