5-bromo-1,2,3,4-tetrahydrocyclopenta[b]indole | 420802-56-8

• 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: 5-bromo-1,2,3,4-tetrahydrocyclopenta[b]indole
• CAS: 420802-56-8
• 化学式: C₁₁H₁₀BrN
• 分子量: 236.111
• InChiKey: OBZLZOLGKNHTNA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  13
• 可旋转键数：
  0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  15.8
• 氢给体数：
  1
• 氢受体数：
  0

反应信息

• 作为产物：
  描述：

  苯肼,盐酸盐 在 吡啶 、 溴 作用下， 以 二氯甲烷 为溶剂， 反应 31.5h， 生成 5-bromo-1,2,3,4-tetrahydrocyclopenta[b]indole
  参考文献：
  名称：

  通过溴化-还原序列高效合成溴环戊酮[ b ]吲哚。

  摘要：

  在一锅反应中，用过量的吡啶-Br 2电荷转移络合物（PyBr 2）以高收率选择性地取代取代的环戊[ b ]吲哚，以提供5和/或7-溴吲哚。该机理涉及形成加合物（在中心双键上加成溴），其随后被Zn和AcOH原位还原。环戊基和苯环中的各种官能团是可容忍的。

  DOI：

  10.1002/jhet.5570400214

文献信息

• Process for the preparation of 1,2,3,4,8,9,10,10a-octahydro-7bH-cyclopenta [b] [1,4] diazepino- [6,7,1-hi] indole derivatives
  申请人：——

  公开号：US20020055504A1

  公开（公告）日：2002-05-09

  This invention provides a process for the preparation of 1, 2, 3, 4, 8, 9, 10, 10a-octahydro-7bH-cyclopenta[b][1,4]diazepino[6, 7, 1-hi]indole derivatives of the general formula: 1 wherein: R is H, alkyl, cycloalkyl, —CH 2 -cycloalkyl, acyl, aryl or aroyl; R 1 , R 2 , R 4 and R 5 are H, hydroxy, alkyl, cycloalkyl, alkoxy, halogen, fluorinated alkyl, —CN, —NH—SO 2 -alkyl, —SO 2 —NH-alkyl, alkyl amide, amino, alkylamino, dialkylmino, fluorinated alkoxy, acyl, aryl or aroyl; R 3 is H, alkyl, cycloalkyl, alkoxy, fluorinated alkyl, alkyl sulfonamide, alkyl amide, amino, alkylamino, dialkylmino, fluorinated alkoxy, acyl, aryl or aroyl; or a pharmaceutically acceptable salt thereof, as well as intermediates for their synthesis.

  该发明提供了一种制备1、2、3、4、8、9、10、10a-八氢-7bH-环戊[b][1,4]二氮杂环[6,7,1-嗪]吲哚衍生物的方法，其通式为：1其中：R为H、烷基、环烷基、—CH2-环烷基、酰基、芳基或芳酰基；R1、R2、R4和R5为H、羟基、烷基、环烷基、烷氧基、卤素、氟代烷基、—CN、—NH—SO2-烷基、—SO2—NH-烷基、烷基酰胺、氨基、烷基氨基、二烷基氨基、氟代烷氧基、酰基、芳基或芳酰基；R3为H、烷基、环烷基、烷氧基、氟代烷基、烷基磺酰胺、烷基酰胺、氨基、烷基氨基、二烷基氨基、氟代烷氧基、酰基、芳基或芳酰基；或其药学上可接受的盐，以及其合成的中间体。
• CYCLOPENTA[b][1,4]DIAZEPINO[6,7,1-hi]INDOLES AND DERIVATIVES
  申请人：Sabb Louise Annmarie

  公开号：US20080009480A1

  公开（公告）日：2008-01-10

  This invention provides compounds of the formulae: wherein: R 1 is hydrogen, —C(O)CH 3 or alkyl of 1-6 carbon atoms; R 2 and R 3 are each, independently, hydrogen, alkyl of 1-6 carbon atoms, cycloalkyl, alkoxy of 1-6 carbon atoms, —CH 2 OH, fluoroalkyl, alkyl sulfonamide of 1-6 carbon atoms, alkyl amide of 1-6 carbon atoms, amino, alkylamino of 1-6 carbon atoms, dialkylamino of 1-6 carbon atoms per alkyl moiety, fluoroalkoxy of 1-6 carbon atoms, acyl of 2-7 carbon atoms, aryl, or aroyl; R 4 and R 5 are each, independently, hydrogen, alkyl of 1-6 carbon atoms, alkoxy of 1-6 carbon atoms, halogen, fluoroalkyl, —CN, alkyl sulfonamide of 1-6 carbon atoms, alkyl amide of 1-6 carbon atoms, amino, alkylamino of 1-6 carbon atoms, dialkylamino of 1-6 carbon atoms per alkyl moiety, fluoroalkoxy of 1-6 carbon atoms, acyl of 2-7 carbon atoms, or aroyl; R 6 and R 7 are each independently hydrogen, C 1 -C 6 alkyl or cycloalkyl; or a pharmaceutically acceptable salt thereof, as well as pharmaceutical compositions containing these compounds and methods for their use, including treatment of obsessive-compulsive disorder, panic disorder, depression, anxiety, generalized anxiety disorder, schizophrenia, migraine, sleep disorders, eating disorders, obesity, epilepsy, and spinal cord injury.

  这项发明提供了以下式子的化合物：其中：R1为氢、—C（O）CH3或1-6个碳原子的烷基；R2和R3各自独立地为氢、1-6个碳原子的烷基、环烷基、1-6个碳原子的烷氧基、—CH2OH、氟代烷基、1-6个碳原子的烷基磺酰胺、1-6个碳原子的烷基酰胺、氨基、1-6个碳原子的烷基氨基、每个烷基成分的1-6个碳原子的双烷基氨基、1-6个碳原子的氟代烷氧基、2-7个碳原子的酰基、芳基或芳酰基；R4和R5各自独立地为氢、1-6个碳原子的烷基、1-6个碳原子的烷氧基、卤素、氟代烷基、—CN、1-6个碳原子的烷基磺酰胺、1-6个碳原子的烷基酰胺、氨基、1-6个碳原子的烷基氨基、每个烷基成分的1-6个碳原子的双烷基氨基、1-6个碳原子的氟代烷氧基、2-7个碳原子的酰基或芳酰基；R6和R7各自独立地为氢、C1-C6烷基或环烷基；或其药学上可接受的盐，以及包含这些化合物的制药组合物和它们的使用方法，包括治疗强迫症、恐慌症、抑郁症、焦虑症、广泛性焦虑症、精神分裂症、偏头痛、睡眠障碍、进食障碍、肥胖症、癫痫和脊髓损伤。
• A facile approach to the synthesis of 5,7-disubstituted indoles via a highly selective lithium–bromine exchange of 5,7-dibromoindoles
  作者：Lianhai Li、Andrew Martins

  DOI：10.1016/s0040-4039(02)02658-8

  日期：2003.1

  A general approach to the synthesis of 5,7-disubstituted indoles has been developed based upon a highly selective lithium-bromine exchange reaction at the 7-position when 1-alkyl-5,7-dibromoindoles were treated with t-BuLi in ether. The resulting 5-bromo-7-lithiated indoles could react with various electrophiles to afford 5-bromo-7-substituted indoles (6) upon work-up. Without isolation of 6, the intermediates thus obtained could be exposed to a second lithium-bromine exchange reaction in a one-pot procedure and further reacted with various electrophiles to afford 5,7-disubstituted indoles (1). (C) 2003 Published by Elsevier Science Ltd.
• Synthesis of substituted indoles via a highly selective 7-lithiation of 4,7-dibromoindoles and the effect of indole-nitrogen on regioselectivity
  作者：Lianhai Li、Andrew Martins

  DOI：10.1016/s0040-4039(03)01482-5

  日期：2003.8

  We have developed an efficient synthetic pathway to rapidly access 4-bromoindoles, 4-substituted indoles, 4-bromo-7-substituted indoles, and 4,7-disubstituted indoles using a highly selective lithiation at the 7-position of 1-alkyl-4,7-dibromoindoles when treated with t-BuLi in ether. Based upon the selectivity obtained with 5,7-dibromoindoles in our previous study and with 4,7-dibromoindoles in the current study, we conclude that the alkylated indole nitrogen plays an important role in controlling selectivity. (C) 2003 Elsevier Ltd. All rights reserved.
• CYCLOPENTA[B][1,4] DIAZEPINO[6,7,1-HI]INDOLES AS 5HT2C ANTAGONISTS
  申请人：Wyeth

  公开号：EP1330457A2

  公开（公告）日：2003-07-30