1,2,3,4-tetrahydro-6-methoxycyclopent[b]indole | 327021-89-6

• 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: 1,2,3,4-tetrahydro-6-methoxycyclopent[b]indole
• 英文别名: 1,2,3,4-tetrahydro-6-methoxy-cyclopent[b]indole；6-Methoxy-1,2,3,4-tetrahydrocyclopenta[b]indole
• CAS: 327021-89-6
• 化学式: C₁₂H₁₃NO
• 分子量: 187.241
• InChiKey: VSAFAJXSNSESEN-UHFFFAOYSA-N

物化性质

• 沸点：
  341.5±37.0 °C(Predicted)
• 密度：
  1.208±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  14
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  25
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为产物：
  描述：

  1,2-环戊二醇 、 间氨基苯甲醚 在 四氟硼酸-二乙醚络合物 、 {[(PCy₃)(CO)RuH]₄(μ-O)(μ-OH)₂} 、 环戊烯 作用下， 以 1,4-二氧六环 为溶剂， 反应 14.0h， 以62%的产率得到1,2,3,4-tetrahydro-6-methoxycyclopent[b]indole
  参考文献：
  名称：

  芳胺与1,2-和1,3-二元醇脱水CH偶联反应催化合成取代的吲哚和喹啉

  摘要：

  The cationic ruthenium-hydride complex catalyzes the dehydrative C-H coupling reaction of arylamines with 1,2-diols to form the indole products. The analogous coupling of arylamines with 1,3-diols afforded the substituted, quinolines. The catalytic method directly forms these coupling products in a highly regioselective manner without generating any toxic byprodficts.

  DOI：

  10.1021/acs.organomet.6b00273

文献信息

• Indole derivatives process for their preparation, pharmaceutical compositions containing them and their medicinal application
  申请人：Vernalis Research Limited

  公开号：US06706750B1

  公开（公告）日：2004-03-16

  A chemical compound of formula (I) wherein: R1 and R2 are independently selected from hydrogen and alkyl; R3 is alkyl; R4, R6 and R7 are independently selected from hydrogen, halogen, hydroxy, alkyl, aryl, amino, alkylamino, dialkylamino, alkoxy, aryloxy, alkylthio, alkylsufoxyl, alkylsulfonyl, nitro, carbonitrile, carbo-alkoxy, carbo-aryloxy and carboxyl; R5 is selected from hydrogen, halogen, hydroxy, alkyl, aryl, amino, alkylamino, dialkylamino, alkoxy, aryloxy, alkylthio, alkylsulfoxyl, alkylsulfonyl, nitro, carbonitrile, carbo-alkoxy, carbo-aryloxy and carboxyl; A is a 5- or 6-membered partially unsaturated or aromatic heterocyclic ring or a 5- or 6-membered partially unsaturated carbocyclic ring, wherein if A is a 6-membered partially unsaturated carbocyclic ring then at least one of R4 to R7 is other than hydrogen, and pharmaceutically acceptable salts, addition compounds and prodrugs thereof, and the use thereof in therapy, particularly as an agonist or antagonist of a 5HT receptor, particularly a 5HT2C receptor, for instance in the treatment of disorders of the central nervous system; damage to the central nervous system; cardiovascular disorders; gastrointestinial disorders; diabetes insipidus, and sleep apnea, and particularly for the treatment of obesity.

  一种化学化合物的化学式（I），其中：R1和R2独立选择自氢和烷基；R3是烷基；R4、R6和R7独立选择自氢、卤素、羟基、烷基、芳基、氨基、烷基氨基、二烷基氨基、烷氧基、芳氧基、烷基硫基、烷基亚砜基、烷基磺基、硝基、碳氰基、羰基烷氧基、羰基芳氧基和羧基；R5选择自氢、卤素、羟基、烷基、芳基、氨基、烷基氨基、二烷基氨基、烷氧基、芳氧基、烷基硫基、烷基亚砜基、烷基磺基、硝基、碳氰基、羰基烷氧基、羰基芳氧基和羧基；A是一个5-或6-成员部分不饱和或芳香杂环环或一个5-或6-成员部分不饱和脂环环，如果A是一个6-成员部分不饱和脂环环，则R4至R7中至少一个不是氢，以及其在治疗中的使用，特别是作为5HT受体的激动剂或拮抗剂，特别是5HT2C受体，例如在治疗中枢神经系统疾病；中枢神经系统损伤；心血管疾病；胃肠疾病；尿崩症和睡眠呼吸暂停症，特别是用于肥胖症的治疗。
• Indoline derivatives and method of treating obesity
  申请人：——

  公开号：US06479534B1

  公开（公告）日：2002-11-12

  The present invention relates to indoline derivatives. These compounds are especially useful for the prevention and treatment of disorders of the central nervous system; damage to the central nervous system; cardiovascular disorders; gastrointestinal disorders; diabetes, sleep apnea, and especially for the treatment and prevention of obesity.

  本发明涉及吲哚啉衍生物。这些化合物特别适用于预防和治疗中枢神经系统紊乱；中枢神经系统损伤；心血管疾病；胃肠道疾病；糖尿病，睡眠呼吸暂停症，尤其是用于肥胖症的治疗和预防。
• INDOLINE DERIVATIVES AND METHOD OF TREATING OBESITY
  申请人：——

  公开号：US20020183349A1

  公开（公告）日：2002-12-05

  The present invention relates to indoline derivatives. These compounds are especially useful for the prevention and treatment of disorders of the central nervous system; damage to the central nervous system; cardiovascular disorders; gastrointestinal disorders; diabetes, sleep apnea, and especially for the treatment and prevention of obesity.

  本发明涉及吲哚啉衍生物。这些化合物特别适用于预防和治疗中枢神经系统疾病；中枢神经系统损伤；心血管疾病；胃肠道疾病；糖尿病、睡眠呼吸暂停症，特别是用于肥胖症的治疗和预防。
• Efficient synthesis of indoles using [3,3]-sigmatropic rearrangement of N-trifluoroacetyl enehydrazines
  作者：Okiko Miyata、Norihiko Takeda、Yasuo Kimura、Yoshiji Takemoto、Norimitsu Tohnai、Mikiji Miyata、Takeaki Naito

  DOI：10.1016/j.tet.2006.01.087

  日期：2006.4

  [3,3]-Sigmatropic rearrangement of N-triflluoroacetyl enehydrazines provides a novel method for the construction of indoles. N-Trifluoroacetyl enehydrazine having a cyclopentene ring smoothly underwent [3,3]-sign-tatropic rearrangement followed by cyclization to give indolines in excellent yield. On the other hand, both cyclohexenyl N-trifluoroacetyl enchydrazine and acyclic N-trifluoroacetyl enehydrazine gave indoles in good yield. Additionally, the substituent effect on the benzene ring was also studied. The rearrangement of N-trifluoroacetyl enchydrazines proceeded smoothly even Linder either aqueous or solvent-free conditions. (c) 2006 Elsevier Ltd. All rights reserved.
• INDOLE DERIVATIVES, PROCESSES FOR THEIR PREPARATION, PHARMACEUTICAL COMPOSITIONS CONTAINING THEM AND THEIR MEDICINAL APPLICATION
  申请人：VERNALIS RESEARCH LIMITED

  公开号：EP1202965B1

  公开（公告）日：2004-10-13