butyl 5-bromoindole-3-carboxylate | 1392408-44-4

• 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
• 英文名称: butyl 5-bromoindole-3-carboxylate
• 英文别名: butyl 5-bromo-1H-indole-3-carboxylate
• CAS: 1392408-44-4
• 化学式: C₁₃H₁₄BrNO₂
• 分子量: 296.164
• InChiKey: DYZSLSMLMKWMJI-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.6
• 重原子数：
  17
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  42.1
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  5-溴吲哚 、 一氧化碳 、 正丁醇 在 碘 、 palladium diacetate 、 potassium carbonate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 100.0 ℃ 、101.33 kPa 条件下， 反应 24.0h， 以68%的产率得到butyl 5-bromoindole-3-carboxylate
  参考文献：
  名称：

  A General Method for Palladium-Catalyzed Direct Carbonylation of Indole with Alcohol and Phenol

  摘要：

  A novel strategy involving a first oxidative iodination and subsequent Pd-0-catalyzed carbonylation to yield indole-3-carboxylate has been developed. It showed perfect generality to indole, alcohol, and phenol. The current methodology could also be conveniently applied to the synthesis of biologically active tropisetron from simple indole and tropine.

  DOI：

  10.1021/ol3017726

文献信息

• INDOLE AND AZAINDOLE DERIVATIVE HAVING AMPK-ACTIVATING ACTIVITY
  申请人：SHIONOGI & CO., LTD

  公开号：US20150203450A1

  公开（公告）日：2015-07-23

  Disclosed is a compound which is useful as an AMPK activator. A compound represented by formula: or its pharmaceutically acceptable salt, wherein Y is substituted or unsubstituted alkyl, substituted or unsubstituted alkenyl, substituted or unsubstituted alkynyl, substituted or unsubstituted aryl, substituted or unsubstituted heteroaryl, substituted or unsubstituted cycloalkyl, substituted or unsubstituted cycloalkenyl, or substituted or unsubstituted heterocyclyl; T is —CR 7 ═ or —N═; U is —CR 8 ═ or —N═; R 2 is hydrogen, halogen, cyano, nitro, carboxy, substituted or unsubstituted alkyl, substituted or unsubstituted alkenyl, substituted or unsubstituted acyl, substituted or unsubstituted carbamoyl, substituted or unsubstituted alkylthio, substituted or unsubstituted alkylsulfinyl, substituted or unsubstituted alkylsulfonyl, or substituted or unsubstituted alkyloxycarbonyl; R 3 is halogen, substituted or unsubstituted alkyl, substituted or unsubstituted alkenyl, substituted or unsubstituted alkynyl, substituted or unsubstituted aryl, substituted or unsubstituted heteroaryl, substituted or unsubstituted cycloalkyl, substituted or unsubstituted cycloalkenyl, substituted or unsubstituted heterocyclyl, or the like; and R 4 , R 7 and R 8 are each independently hydrogen, halogen, hydroxy, cyano, nitro, carboxy, substituted or unsubstituted alkyl, substituted or unsubstituted alkenyl, substituted or unsubstituted alkynyl, substituted or unsubstituted aryl, substituted or unsubstituted heteroaryl, substituted or unsubstituted cycloalkyl, substituted or unsubstituted cycloalkenyl, substituted or unsubstituted heterocyclyl, or the like.

  本申请公开了一种作为AMPK激活剂有用的化合物。一种由以下结构表示的化合物或其药学上可接受的盐，其中Y被取代或未取代的烷基，取代或未取代的烯基，取代或未取代的炔基，取代或未取代的芳基，取代或未取代的杂环芳基，取代或未取代的环烷基，取代或未取代的环烯基，或取代或未取代的杂环烷基；T为—CR7═或—N═；U为—CR8═或—N═；R2为氢，卤素，氰基，硝基，羧基，取代或未取代的烷基，取代或未取代的烯基，取代或未取代的酰基，取代或未取代的氨基甲酰基，取代或未取代的烷基硫基，取代或未取代的烷基亚砜基，取代或未取代的烷基砜基，或取代或未取代的烷氧羰基；R3为卤素，取代或未取代的烷基，取代或未取代的烯基，取代或未取代的炔基，取代或未取代的芳基，取代或未取代的杂环芳基，取代或未取代的环烷基，取代或未取代的环烯基，取代或未取代的杂环烷基，或类似物；且R4、R7和R8分别独立地为氢，卤素，羟基，氰基，硝基，羧基，取代或未取代的烷基，取代或未取代的烯基，取代或未取代的炔基，取代或未取代的芳基，取代或未取代的杂环芳基，取代或未取代的环烷基，取代或未取代的环烯基，取代或未取代的杂环烷基，或类似物。
• INDOLE AND AZAINDOLE DERIVATIVES EACH HAVING AMPK-ACTIVATING ACTIVITY
  申请人：Shionogi & Co., Ltd.

  公开号：EP2963013A1

  公开（公告）日：2016-01-06

  Disclosed is a compound which is useful as an AMPK activator. A compound represented by formula: or its pharmaceutically acceptable salt, wherein Y is substituted or unsubstituted alkyl, substituted or unsubstituted alkenyl, substituted or unsubstituted alkynyl, substituted or unsubstituted aryl, substituted or unsubstituted heteroaryl, substituted or unsubstituted cycloalkyl, substituted or unsubstituted cycloalkenyl, or substituted or unsubstituted heterocyclyl; T is -CR7= or -N=; U is -CR8= or -N=; R2 is hydrogen, halogen, cyano, nitro, carboxy, substituted or unsubstituted alkyl, substituted or unsubstituted alkenyl, substituted or unsubstituted acyl, substituted or unsubstituted carbamoyl, substituted or unsubstituted alkylthio, substituted or unsubstituted alkylsulfinyl, substituted or unsubstituted alkylsulfonyl, or substituted or unsubstituted alkyloxycarbonyl; R3 is halogen, substituted or unsubstituted alkyl, substituted or unsubstituted alkenyl, substituted or unsubstituted alkynyl, substituted or unsubstituted aryl, substituted or unsubstituted heteroaryl, substituted or unsubstituted cycloalkyl, substituted or unsubstituted cycloalkenyl, substituted or unsubstituted heterocyclyl, or the like; and R4, R7 and R8 are each independently hydrogen, halogen, hydroxy, cyano, nitro, carboxy, substituted or unsubstituted alkyl, substituted or unsubstituted alkenyl, substituted or unsubstituted alkynyl, substituted or unsubstituted aryl, substituted or unsubstituted heteroaryl, substituted or unsubstituted cycloalkyl, substituted or unsubstituted cycloalkenyl, substituted or unsubstituted heterocyclyl, or the like.

  本发明公开了一种可用作 AMPK 激活剂的化合物。一种由式表示的化合物： 或其药学上可接受的盐、 其中 Y 是取代或未取代的烷基、取代或未取代的烯基、取代或未取代的炔基、取代或未取代的芳基、取代或未取代的杂芳基、取代或未取代的环烷基、取代或未取代的环烯基、取代或未取代的杂环基； T 是-CR7= 或-N=； U 是-CR8= 或-N=； R2 是氢、卤素、氰基、硝基、羧基、取代或未取代的烷基、取代或未取代的烯基、取代或未取代的酰基、取代或未取代的氨基甲酰基、取代或未取代的烷硫基、取代或未取代的烷硫基、取代或未取代的烷磺酰基、取代或未取代的烷氧羰基； R3 是卤素、取代或未取代的烷基、取代或未取代的烯基、取代或未取代的炔基、取代或未取代的芳基、取代或未取代的杂芳基、取代或未取代的环烷基、取代或未取代的环烯基、取代或未取代的杂环基，或类似物；和 R4、R7 和 R8 各自独立地为氢、卤素、羟基、氰基、硝基、羧基、取代或未取代的烷基、取代或未取代的烯基、取代或未取代的炔基、取代或未取代的芳基、取代或未取代的杂芳基、取代或未取代的环烷基、取代或未取代的环烯基、取代或未取代的杂环基或类似物。
• A General Method for Palladium-Catalyzed Direct Carbonylation of Indole with Alcohol and Phenol
  作者：Rui Lang、Lijun Shi、Dengfeng Li、Chungu Xia、Fuwei Li

  DOI：10.1021/ol3017726

  日期：2012.8.17

  A novel strategy involving a first oxidative iodination and subsequent Pd-0-catalyzed carbonylation to yield indole-3-carboxylate has been developed. It showed perfect generality to indole, alcohol, and phenol. The current methodology could also be conveniently applied to the synthesis of biologically active tropisetron from simple indole and tropine.