(2,4-dibromo-6,7,8,9-tetrahydro-5H-carbazol-3-yl)-dimethyl-amine | 704909-96-6

• 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: (2,4-dibromo-6,7,8,9-tetrahydro-5H-carbazol-3-yl)-dimethyl-amine
• 英文别名: 2,4-dibromo-N,N-dimethyl-6,7,8,9-tetrahydro-5H-carbazol-3-amine
• CAS: 704909-96-6
• 化学式: C₁₄H₁₆Br₂N₂
• 分子量: 372.102
• InChiKey: MBXLTVCSBNRVRG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.8
• 重原子数：
  18
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  19
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  (2,4-dibromo-6,7,8,9-tetrahydro-5H-carbazol-3-yl)-dimethyl-amine 在 palladium diacetate sodium tetrahydroborate 、 四甲基乙二胺 、 R-(+)-1,1'-联萘-2,2'-双二苯膦 作用下， 以 四氢呋喃 为溶剂， 反应 24.0h， 以74%的产率得到(4-bromo-6,7,8,9-tetrahydro-5H-carbazol-3-yl)-dimethyl-amine
  参考文献：
  名称：

  Palladium-Catalyzed Regioselective Hydrodebromination of Dibromoindoles:  Application to the Enantioselective Synthesis of Indolodioxane U86192A

  摘要：

  A novel approach to the selective preparation of 4-bromoindoles was developed via Pd(OAc)(2)/rac-BINAP catalytic reactions. A variety of 4,6-dibromoindoles were transformed to 4-bromoindoles with high regioselectivity. This methodology, along with C-N and C-O bond-forming reactions developed in our laboratory, was applied to the enantioselective synthesis of indolodioxane U86192A, an antihypertensive agent.

  DOI：

  10.1021/jo035819k
• 作为产物：
  描述：

  (2,6-dibromo-4-iodophenyl)-dimethylamine 在 copper(l) iodide 、 caesium carbonate 、 对甲苯磺酸 作用下， 以 乙醇 、 N,N-二甲基甲酰胺 为溶剂， 生成 (2,4-dibromo-6,7,8,9-tetrahydro-5H-carbazol-3-yl)-dimethyl-amine
  参考文献：
  名称：

  Palladium-Catalyzed Regioselective Hydrodebromination of Dibromoindoles:  Application to the Enantioselective Synthesis of Indolodioxane U86192A

  摘要：

  A novel approach to the selective preparation of 4-bromoindoles was developed via Pd(OAc)(2)/rac-BINAP catalytic reactions. A variety of 4,6-dibromoindoles were transformed to 4-bromoindoles with high regioselectivity. This methodology, along with C-N and C-O bond-forming reactions developed in our laboratory, was applied to the enantioselective synthesis of indolodioxane U86192A, an antihypertensive agent.

  DOI：

  10.1021/jo035819k

文献信息

• Palladium-Catalyzed Regioselective Hydrodebromination of Dibromoindoles:  Application to the Enantioselective Synthesis of Indolodioxane U86192A
  作者：Junghyun Chae、Stephen L. Buchwald

  DOI：10.1021/jo035819k

  日期：2004.5.1

  A novel approach to the selective preparation of 4-bromoindoles was developed via Pd(OAc)(2)/rac-BINAP catalytic reactions. A variety of 4,6-dibromoindoles were transformed to 4-bromoindoles with high regioselectivity. This methodology, along with C-N and C-O bond-forming reactions developed in our laboratory, was applied to the enantioselective synthesis of indolodioxane U86192A, an antihypertensive agent.