5-bromo-1,2-dimethyl-1H-indole

• 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-dimethyl-1H-indole
• 英文别名: 1,2-Dimethyl-5-bromoindole；5-bromo-1,2-dimethylindole
• 化学式: C₁₀H₁₀BrN
• 分子量: 224.1
• InChiKey: CTLFMCACJRWVLM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  12
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  4.9
• 氢给体数：
  0
• 氢受体数：
  0

反应信息

• 作为反应物：
  描述：

  5-bromo-1,2-dimethyl-1H-indole 在 copper(l) iodide 、 caesium carbonate 、 N,N-二异丙基乙胺 作用下， 以 异丙醇 为溶剂， 反应 2.0h， 生成 5-bromo-1,2,2'-trimethyl-1'-tosyl-1H,1'H-3,3'-biindole
  参考文献：
  名称：

  通过铜催化的Friedel-Crafts炔丙基化/氢化/芳香化序列合成3,3'-联吲哚

  摘要：

  描述了铜催化的Friedel-Crafts炔丙基化/加氢胺化/芳构化顺序。在催化量的CuI的存在下，该顺序反应可以高效高效地将乙炔基苯并恶嗪酮和吲哚转化为各种3,3'-联吲哚。此外，还证明了其他吲哚-杂芳基分子的合成和轴向手性3,3'-双吲哚的催化不对称形成。

  DOI：

  10.1021/acs.orglett.8b01100
• 作为产物：
  描述：

  5,7-Dibromo-1,2-dimethyl-1H-indole 在 叔丁基锂 作用下， 以 乙醚 为溶剂， 反应 0.17h， 生成 1,2-二甲基吲哚 、 5-bromo-1,2-dimethyl-1H-indole
  参考文献：
  名称：

  A facile approach to the synthesis of 5,7-disubstituted indoles via a highly selective lithium–bromine exchange of 5,7-dibromoindoles

  摘要：

  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.

  DOI：

  10.1016/s0040-4039(02)02658-8

文献信息

• NOVEL CYCLIC BENZIMIDAZOLE DERIVATIVES USEFUL AS ANTI-DIABETIC AGENTS
  申请人：BOOKSER BRETT C.

  公开号：US20100081643A1

  公开（公告）日：2010-04-01

  Novel compounds of the structural formula (I) are activators of AMP-protein kinase and are useful in the treatment, prevention and suppression of diseases mediated by the AMPK-activated protein kinase. The compounds of the present invention are useful in the treatment of Type 2 diabetes, hyperglycemia, metabolic syndrome, obesity, hypercholesterolemia, and hypertension.

  结构式（I）的新化合物是AMP-蛋白激酶的激活剂，并且在治疗、预防和抑制由AMPK激活的蛋白激酶介导的疾病方面非常有用。本发明的化合物在治疗2型糖尿病、高血糖、代谢综合征、肥胖、高胆固醇血症和高血压方面非常有用。
• [EN] NOVEL CYCLIC BENZIMIDAZOLE DERIVATIVES USEFUL ANTI-DIABETIC AGENTS<br/>[FR] NOUVEAUX DÉRIVÉS DE BENZIMIDAZOLE CYCLIQUES UTILES COMME AGENTS ANTI-DIABÉTIQUES
  申请人：MERCK SHARP & DOHME

  公开号：WO2010047982A1

  公开（公告）日：2010-04-29

  Novel compounds of the structural formula (I) are activators of AMP-protein kinase and are useful in the treatment, prevention and suppression of diseases mediated by the AMPK-activated protein kinase. The compounds of the present invention are useful in the treatment of Type 2 diabetes, hyperglycemia, Metabolic Syndrome, obesity, hypercholesterolemia, and hypertension.

  结构式（I）的新化合物是AMP-蛋白激酶的激活剂，并且在治疗、预防和抑制由AMPK激活的蛋白激酶介导的疾病方面非常有用。本发明的化合物在治疗2型糖尿病、高血糖、代谢综合征、肥胖、高胆固醇血症和高血压方面非常有用。
• [EN] NOVEL CYCLIC BENZIMIDAZOLE DERIVATIVES USEFUL ANTI-DIABETIC AGENTS<br/>[FR] NOUVEAUX AGENTS ANTIDIABÉTIQUES UTILES AVEC DES DÉRIVÉS DE BENZIMIDAZOLE CYCLIQUES
  申请人：MERCK SHARP & DOHME

  公开号：WO2010051206A1

  公开（公告）日：2010-05-06

  Novel compounds of the structural formula (I) are activators of AMP-protein kinase and are useful in the treatment, prevention and suppression of diseases mediated by the AMPK- activated protein kinase. The compounds of the present invention are useful in the treatment of Type 2 diabetes, hyperglycemia, metabolic syndrome, obesity, hypercholesterolemia, and hypertension.

  结构式（I）的新化合物是AMP-蛋白激酶的激活剂，并且在治疗、预防和抑制由AMPK激活的蛋白激酶介导的疾病方面非常有用。本发明的化合物在治疗2型糖尿病、高血糖、代谢综合征、肥胖、高胆固醇血症和高血压方面非常有用。
• Cu-Catalyzed Oxidation of C2 and C3 Alkyl-Substituted Indole via Acyl Nitroso Reagents
  作者：Jun Zhang、Saeedeh Torabi Kohlbouni、Babak Borhan

  DOI：10.1021/acs.orglett.8b03185

  日期：2019.1.4

  The selective oxidation of C2-alkyl-substituted indoles to 3-oxindole and the selective C–H oxygenation or amination of C2,C3-dialkyl-substituted indoles at C2 are reported under mild conditions. The position of the alkyl substitution on the indole directs the reaction to different pathways under similar conditions.

  据报道，在温和的条件下，C2-烷基取代的吲哚被选择性氧化为3-羟吲哚，以及在C2处对C2，C3-二烷基取代的吲哚进行选择性的CH氧化或胺化。吲哚上烷基的取代位置将反应引导至相似条件下的不同途径。
• Mild Aminoacylation of Indoles and Pyrroles through a Three-Component Reaction with Ynol Ethers and Sulfonyl Azides
  作者：Joshua S. Alford、Huw M. L. Davies

  DOI：10.1021/ja5058967

  日期：2014.7.23

  An effective method for aminoacylation of indoles and pyrroles has been achieved. The transformation involves a multicomponent one-pot cascade reaction between indoles or pyrroles, ynol ethers, and sulfonyl azides, creating four different bonds regioselectively through N-sulfonyltriazole intermediates. The oxo-tryptamines and oxo-pyrroloethanamines are generated in moderate to high yields under mild

  已经实现了吲哚和吡咯氨酰化的有效方法。该转化涉及吲哚或吡咯、炔醇醚和磺酰叠氮化物之间的多组分一锅级联反应，通过 N-磺酰基三唑中间体区域选择性地产生四种不同的键。在温和的反应条件下，以中等至高产率生成氧代色胺和氧代吡咯烷胺。