5-氯-3-(1-甲基哌啶-4-基)-1H-吲哚 | 301856-30-4

• 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
• 中文名称: 5-氯-3-(1-甲基哌啶-4-基)-1H-吲哚
• 中文别名: 5-氯-3-(1-甲基-4-哌啶基)吲哚
• 英文名称: 5-chloro-3-(1-methylpiperidin-4-yl)-1H-indole
• 英文别名: 5-Chloro-3-(1-methyl-4-piperidinyl)indole
• CAS: 301856-30-4
• 化学式: C₁₄H₁₇ClN₂
• 分子量: 248.755
• InChiKey: UVGVFOXMUYGAIA-UHFFFAOYSA-N

物化性质

• 沸点：
  403.4±45.0 °C(Predicted)
• 密度：
  1?+-.0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  17
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  19
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  5-氯-3-(1-甲基哌啶-4-基)-1H-吲哚 、 对氟苯甲酰氯 生成 5-Chloro-1-(4-fluorobenzoyl)-3-(1-methyl-4-piperidinyl)indole
  参考文献：
  名称：

  Piperidine-indole compounds having 5-HT.sub.6 affinity

  摘要：

  本文描述了对5-HT.sub.6受体具有亲和力的化合物，其具有以下通式：其中：R.sup.1选自H和C.sub.1-4烷基的群组；R.sup.2选自H、C.sub.1-4烷基和苄基的群组；——表示单键或双键；R.sup.3选自COR.sup.5和SO.sub.2R.sup.5的群组；R.sup.4a选自H、OH、卤素、C.sub.1-4烷基和C.sub.1-4烷氧基的群组；R.sup.4b选自H、羟基、卤素、C.sub.3-7环烷氧基、C.sub.1-4烷氧基、C.sub.1-4烷基、苄氧基、苯氧基、三氟甲基、三氟甲氧基和乙烯基的群组；R.sup.4c选自H、OH、卤素、C.sub.1-4烷基和C.sub.1-4烷氧基的群组；R.sub.4d选自H、OH、卤素、C.sub.1-4烷基和C.sub.1-4烷氧基的群组；R.sup.5选自苯基、吡啶基、噻吩基、喹啉基和萘基，其中可以选用1-4个从C.sub.1-4烷氧基、C.sub.1-4烷基、卤素、硝基、三氟甲基、三氟甲氧基、1,2-亚甲二氧基、C.sub.1-4烷基羰基、C.sub.1-4烷氧基羰基和C.sub.1-4烷基S--中选择的取代基。还描述了这些化合物作为药物治疗5-HT.sub.6受体受到抑制的疾病，如精神分裂症的用途。

  公开号：

  US06133287A1
• 作为产物：
  描述：

  N-甲基-4-哌啶酮 在 Rh(acac)2(CO)2 硫酸 、 氢气 、 sodium hydride 作用下， 以 二甲基亚砜 为溶剂， 20.0~100.0 ℃ 、6.0 MPa 条件下， 反应 72.5h， 生成 5-氯-3-(1-甲基哌啶-4-基)-1H-吲哚
  参考文献：
  名称：

  Synthesis of Pharmacologically Relevant Indoles with Amine Side Chains via Tandem Hydroformylation/Fischer Indole Synthesis

  摘要：

  The sequence of hydroformylation and Fischer indole synthesis starting from amino olefins and aryl hydrazines is described. In a convergent manner, the two units bearing pharmacologically relevant substituents are assembled in the final indolization step. This modular and diversity-oriented approach to tryptamines and homotryptamines can be conducted in water and allows synthesis of branched and nonbranched tryptamines as well as tryptamine-based pharmaceuticals such as the 5-HT1D agonist L 775 606.

  DOI：

  10.1021/jo050464l

文献信息

• PIPERIDINE-INDOLE COMPOUNDS HAVING 5-HT6 AFFINITY
  申请人：NPS Allelix Corp.

  公开号：EP1173432B9

  公开（公告）日：2008-10-15
• US6133287A
  申请人：——

  公开号：US6133287A

  公开（公告）日：2000-10-17
• [EN] PIPERIDINE-INDOLE COMPOUNDS HAVING 5-HT6 AFFINITY<br/>[FR] COMPOSES PIPERIDINE-INDOL AYANT UNE AFFINITE AVEC 5-HT6
  申请人：ALLELIX BIOPHARMA

  公开号：WO2000063203A1

  公开（公告）日：2000-10-26

  Described herein are indole compounds with affinity for the 5-HT6 receptor, which have general formula (I) wherein, R1 is selected from the group consisting of H and C¿1-4?alkyl; R?2¿ is selected from the group consisting of H, C¿1-4?alkyl and benzyl; ----- represents a single or double bond; R?3¿ is selected from the group consisting of COR5 and SO¿2?R?5; R4a¿ is selected from the group consisting of H, OH, halo, C¿1-4?alkyl and C1-4alkoxy; R?4b¿ is selected from the group consisting of H, hydroxy, halo, C¿3-7?cycloalkyloxy, C1-4alkoxy, C1-4alkyl, benzyloxy, phenoxy, trifluoromethyl, trifluoromethoxy and vinyl; R?4c¿ is selected from the group consisting of H, OH, halo, C¿1-4?alkyl and C1-4alkoxy; R?4d¿ is selected from the group consisting of H, OH, halo, C¿1-4?alkyl and C1-4alkoxy; and R?5¿ is selected from the group consisting of phenyl, pyridyl, thienyl, quinolinyl and naphthyl which are optionally substituted with 1-4 substituents selected from C¿1-4?alkoxy, C1-4alkyl, halo, nitro, trifluoromethyl, trifluoromethoxy, 1,2-methylenedioxy, C1-4alkylcarbonyl, C1-4alkoxycarbonyl and C1-4alkylS-. Also described is the use of the compounds as pharmaceuticals to treat indications where inhibition of the 5-HT6 receptor is implicated, such as schizophrenia.
• Piperidine-indole compounds having 5-HT.sub.6 affinity
  申请人：Allelix Biopharmaceuticals Inc.

  公开号：US06133287A1

  公开（公告）日：2000-10-17

  Described herein are compounds with affinity for the 5-HT.sub.6 receptor, which have the general formula: wherein: R.sup.1 is selected from the group consisting of H and C.sub.1-4 alkyl; R.sup.2 is selected from the group consisting of H, C.sub.1-4 alkyl and benzyl; -- -- -- represents a single or double bond; R.sup.3 is selected from the group consisting of COR.sup.5 and SO.sub.2 R.sup.5 ; R.sup.4a is selected from the group consisting of H, OH, halo, C.sub.1-4 alkyl and C.sub.1-4 alkoxy; R.sup.4b is selected from the group consisting of H, hydroxy, halo, C.sub.3-7 cycloalkyloxy, C.sub.1-4 alkoxy, C.sub.1-4 alkyl, benzyloxy, phenoxy, trifluoromethyl, trifluoromethoxy and vinyl; R.sup.4c is selected from the group consisting of H, OH, halo, C.sub.1-4 alkyl and C.sub.1-4 alkoxy; R.sub.4d is selected from the group consisting of H, OH, halo, C.sub.1-4 alkyl and C.sub.1-4 alkoxy; and R.sup.5 is selected from the group consisting of phenyl, pyridyl, thienyl, quinolinyl and naphthyl which are optionally substituted with 1-4 substituents selected from C.sub.1-4 alkoxy, C.sub.1-4 alkyl, halo, nitro, trifluoromethyl, trifluoromethoxy, 1,2-methylenedioxy, C.sub.1-4 alkylcarbonyl, C.sub.1-4 alkoxycarbonyl and C.sub.1-4 alkylS--. Also described is the use of these compounds as pharmaceuticals to treat indications where inhibition of the 5-HT.sub.6 receptor is implicated, such as schizophrenia.

  本文描述了与5-HT.sub.6受体亲和力的化合物，其具有以下一般公式：其中：R.sup.1选自H和C.sub.1-4烷基组; R.sup.2选自H、C.sub.1-4烷基和苄基组; -- -- --代表单键或双键; R.sup.3选自COR.sup.5和SO.sub.2R.sup.5组; R.sup.4a选自H、OH、卤素、C.sub.1-4烷基和C.sub.1-4烷氧基组; R.sup.4b选自H、羟基、卤素、C.sub.3-7环烷氧基、C.sub.1-4烷氧基、C.sub.1-4烷基、苄氧基、苯氧基、三氟甲基、三氟甲氧基和乙烯基组; R.sup.4c选自H、OH、卤素、C.sub.1-4烷基和C.sub.1-4烷氧基组; R.sub.4d选自H、OH、卤素、C.sub.1-4烷基和C.sub.1-4烷氧基组; R.sup.5选自苯基、吡啶基、噻吩基、喹啉基和萘基，可选择地用1-4个来自C.sub.1-4烷氧基、C.sub.1-4烷基、卤素、硝基、三氟甲基、三氟甲氧基、1,2-亚甲二氧基、C.sub.1-4烷基羰基、C.sub.1-4烷氧羰基和C.sub.1-4烷基硫代基的取代基取代。还描述了将这些化合物用作药物治疗5-HT.sub.6受体受抑制相关的适应症，如精神分裂症。
• Synthesis of Pharmacologically Relevant Indoles with Amine Side Chains via Tandem Hydroformylation/Fischer Indole Synthesis
  作者：Axel M. Schmidt、Peter Eilbracht

  DOI：10.1021/jo050464l

  日期：2005.7.1

  The sequence of hydroformylation and Fischer indole synthesis starting from amino olefins and aryl hydrazines is described. In a convergent manner, the two units bearing pharmacologically relevant substituents are assembled in the final indolization step. This modular and diversity-oriented approach to tryptamines and homotryptamines can be conducted in water and allows synthesis of branched and nonbranched tryptamines as well as tryptamine-based pharmaceuticals such as the 5-HT1D agonist L 775 606.