3-溴-7-甲基吲哚 | 903131-21-5

• 物质功能分类: 医药中间体 - 杂环化合物 - 吲哚类化合物
• 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: 3-溴-7-甲基吲哚
• 英文名称: 3-bromo-7-methyl-1H-indole
• CAS: 903131-21-5
• 化学式: C₉H₈BrN
• 分子量: 210.073
• InChiKey: SRFCQQLQYIWNJX-UHFFFAOYSA-N

物化性质

• 沸点：
  322.0±22.0 °C(Predicted)
• 密度：
  1.563±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  11
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.11
• 拓扑面积：
  15.8
• 氢给体数：
  1
• 氢受体数：
  0

安全信息

• 海关编码：
  2933990090

反应信息

• 作为反应物：
  描述：

  3-己炔 、 3-溴-7-甲基吲哚 在 palladium diacetate 、 potassium carbonate 、 三苯基膦 作用下， 以 1,4-二氧六环 为溶剂， 以80 %的产率得到1,2,3,3-tetraethyl-6-methyl-3H-cyclopenta[c]quinoline
  参考文献：
  名称：

  钯催化 3-溴吲哚与内炔环化经螺环环戊二烯中间体合成环戊[c]喹啉

  摘要：

  描述了一种在钯存在下通过 3-溴吲哚与内部炔烃环化构建环戊[ c ]喹啉环的新方法。环戊烷的形成[ c]喹啉环是由螺环环戊二烯中间体的双[1,5]碳σ重排提出的，该中间体是通过3-溴吲哚与内部炔烃的环化原位生成的，涉及连续的双炔插入碳-钯键和吲哚的脱芳构化。目前的研究开发了一种通过在吲哚的C2-C3键上插入一个碳将吡咯环扩环为吡啶的新型反应，并为构建不易合成的三环稠合喹啉衍生物提供了一种简单而独特的路线。通过常规方法访问。

  DOI：

  10.1021/acs.joc.3c00716
• 作为产物：
  描述：

  7-甲基吲哚 在 1,3-二溴-5,5-二甲基海因 作用下， 以 1,4-二氧六环 为溶剂， 以86%的产率得到3-溴-7-甲基吲哚
  参考文献：
  名称：

  Simple and efficient procedures for selective preparation of 3-haloindoles and 2,3-dihaloindoles by using 1,3-dibromo-5,5-dimethylhydantoin and 1,3-dichloro-5,5-dimethylhydantoin

  摘要：

  Simple and efficient synthetic procedures for the selective preparation of 3-bromo/3-chloroindoles and 2,3-dibromo/2,3-dichloroindoles by using 1,3-dibromo-5,5-dimethylhydantoin (DBDMH) and 1,3-dichloro-5,5-dimethylhydantoin (DCDMH) were developed. Using 1,4-dioxane as the solvent, a variety of indoles, treated with 0.55 equiv DBDMH/DCDMH, afford the corresponding 3-bromo/3-chloroindoles selectively in 82-99% yield. In 1,2-dichloroethane (DCE), a series of 2,3-dichloro/2,3-dibromoindoles were selectively obtained in 84-95% yield by treating with DBDMH/DCDMH. All the processes do not need extra catalysts, dry solvents, or harsh reaction conditions. (C) 2015 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2015.01.080

文献信息

• AMIDE COMPOUNDS
  申请人：Nozawa Eisuke

  公开号：US20110028463A1

  公开（公告）日：2011-02-03

  [Problems] To provide a compound that is useful as an agent for treating chronic renal insufficiency or an agent for treating diabetic nephropathy. [Means for Solving Problems] The present inventors have conducted extensive studies on a compound having an EP4 receptor antagonistic action, and as a result, they have found that various amide derivatives having a carboxylic group or an equivalent thereof exhibit an excellent EP4 receptor antagonistic action, thereby completing the present invention. Since the compound of the present invention has an excellent EP4 receptor antagonistic action, it is useful as an agent for preventing and/or treating chronic renal insufficiency or diabetic nephropathy.

  【问题】提供一种可用作治疗慢性肾功能不全或糖尿病肾病的药物化合物。 【解决问题的方法】本发明者对具有EP4受体拮抗作用的化合物进行了广泛的研究，结果发现具有羧酸基或其等效物的各种酰胺衍生物表现出优异的EP4受体拮抗作用，从而完成了本发明。由于本发明的化合物具有优异的EP4受体拮抗作用，因此可用作预防和/或治疗慢性肾功能不全或糖尿病肾病的药物。
• Simple and efficient procedures for selective preparation of 3-haloindoles and 2,3-dihaloindoles by using 1,3-dibromo-5,5-dimethylhydantoin and 1,3-dichloro-5,5-dimethylhydantoin
  作者：Jianwei Yan、Tianjun Ni、Fulin Yan

  DOI：10.1016/j.tetlet.2015.01.080

  日期：2015.2

  Simple and efficient synthetic procedures for the selective preparation of 3-bromo/3-chloroindoles and 2,3-dibromo/2,3-dichloroindoles by using 1,3-dibromo-5,5-dimethylhydantoin (DBDMH) and 1,3-dichloro-5,5-dimethylhydantoin (DCDMH) were developed. Using 1,4-dioxane as the solvent, a variety of indoles, treated with 0.55 equiv DBDMH/DCDMH, afford the corresponding 3-bromo/3-chloroindoles selectively in 82-99% yield. In 1,2-dichloroethane (DCE), a series of 2,3-dichloro/2,3-dibromoindoles were selectively obtained in 84-95% yield by treating with DBDMH/DCDMH. All the processes do not need extra catalysts, dry solvents, or harsh reaction conditions. (C) 2015 Elsevier Ltd. All rights reserved.
• Synthesis of Cyclopenta[<i>c</i>]quinolines by Palladium-Catalyzed Cyclization of 3-Bromoindoles with Internal Alkynes via Spirocyclic Cyclopentadiene Intermediates
  作者：Biao Guo、Jiaying Lv、Le Lu、Ruimao Hua

  DOI：10.1021/acs.joc.3c00716

  日期：2023.7.7

  involving a sequential double alkyne insertion into the carbon–palladium bond and dearomatization of indole. The present studies have developed a novel ring-expansion reaction of the pyrrole ring to pyridine via one carbon insertion into the C2–C3 bond of indoles and provided a simple and distinct route for the construction of tricyclic fused-quinoline derivatives that are not easy to access with conventional

  描述了一种在钯存在下通过 3-溴吲哚与内部炔烃环化构建环戊[ c ]喹啉环的新方法。环戊烷的形成[ c]喹啉环是由螺环环戊二烯中间体的双[1,5]碳σ重排提出的，该中间体是通过3-溴吲哚与内部炔烃的环化原位生成的，涉及连续的双炔插入碳-钯键和吲哚的脱芳构化。目前的研究开发了一种通过在吲哚的C2-C3键上插入一个碳将吡咯环扩环为吡啶的新型反应，并为构建不易合成的三环稠合喹啉衍生物提供了一种简单而独特的路线。通过常规方法访问。