2,2'-dibromo-5-methyl-1,1'-biphenyl-3-ol | 863301-16-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 2,2'-dibromo-5-methyl-1,1'-biphenyl-3-ol
• 英文别名: 2-Bromo-3-(2-bromophenyl)-5-methylphenol；2-bromo-3-(2-bromophenyl)-5-methylphenol
• CAS: 863301-16-0
• 化学式: C₁₃H₁₀Br₂O
• 分子量: 342.03
• InChiKey: CGKYAVKVXNGOBG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.9
• 重原子数：
  16
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.08
• 拓扑面积：
  20.2
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  2,2'-dibromo-5-methyl-1,1'-biphenyl-3-ol 在 盐酸 、 tris(dibenzylideneacetone)dipalladium (0) 、 sodium hydride 、 sodium t-butanolate 、 2-(二环己基膦基)联苯 作用下， 以 四氢呋喃 、 乙醇 、 N,N-二甲基甲酰胺 、 甲苯 为溶剂， 反应 26.25h， 生成 1',8-dimethoxy-3',6-dimethyl-3,9'-bi-9H-carbazole
  参考文献：
  名称：

  One-step construction of carbazoles by way of the palladium-catalyzed double N-arylation reaction and its application to the total synthesis of murrastifoline-A

  摘要：

  The one-step construction of N-substituted carbazoles by way of the Pd-catalyzed double N-arylation reaction of primary amines with 2,2'-dibromobiphenyl is described. Aryl and aliphatic amines including tert-butylamine and a protected glucopyranosylamine were effectively transformed into the corresponding N-substituted carbazoles. The first total synthesis of murrastifoline-A, a biscarbazole alkaloid, based on this methodology is also presented. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2006.04.087
• 作为产物：
  描述：

  toluene-4-sulfonic acid 2-amino-5-methyl-phenyl ester 在 氢氧化钾 、 N-碘代丁二酰亚胺 、 四(三苯基膦)钯 、 硫酸 、 水 、 sodium carbonate 、 溶剂黄146 、 sodium nitrite 作用下， 以 乙醇 、 N,N-二甲基甲酰胺 、 苯 为溶剂， 反应 4.5h， 生成 2,2'-dibromo-5-methyl-1,1'-biphenyl-3-ol
  参考文献：
  名称：

  One-step construction of carbazoles by way of the palladium-catalyzed double N-arylation reaction and its application to the total synthesis of murrastifoline-A

  摘要：

  The one-step construction of N-substituted carbazoles by way of the Pd-catalyzed double N-arylation reaction of primary amines with 2,2'-dibromobiphenyl is described. Aryl and aliphatic amines including tert-butylamine and a protected glucopyranosylamine were effectively transformed into the corresponding N-substituted carbazoles. The first total synthesis of murrastifoline-A, a biscarbazole alkaloid, based on this methodology is also presented. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2006.04.087

文献信息

• Total Synthesis of Murrastifoline-A by Way of the Pd-catalyzed Double N-Arylation of a Carbazolamine with a 2,2’-Dibromobiphenyl Derivative
  作者：Noritaka Chida、Takafumi Kitawaki、Yoko Hayashi

  DOI：10.3987/com-05-10418

  日期：——
• One-step construction of carbazoles by way of the palladium-catalyzed double N-arylation reaction and its application to the total synthesis of murrastifoline-A
  作者：Takafumi Kitawaki、Yoko Hayashi、Akiko Ueno、Noritaka Chida

  DOI：10.1016/j.tet.2006.04.087

  日期：2006.7

  The one-step construction of N-substituted carbazoles by way of the Pd-catalyzed double N-arylation reaction of primary amines with 2,2'-dibromobiphenyl is described. Aryl and aliphatic amines including tert-butylamine and a protected glucopyranosylamine were effectively transformed into the corresponding N-substituted carbazoles. The first total synthesis of murrastifoline-A, a biscarbazole alkaloid, based on this methodology is also presented. (c) 2006 Elsevier Ltd. All rights reserved.