5-chloro-2-(2,2-dibromovinyl)-N-(3-thienylmethyl)aniline | 1067249-41-5

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: 5-chloro-2-(2,2-dibromovinyl)-N-(3-thienylmethyl)aniline
• 英文别名: 5-chloro-2-(2,2-dibromoethenyl)-N-(thiophen-3-ylmethyl)aniline
• CAS: 1067249-41-5
• 化学式: C₁₃H₁₀Br₂ClNS
• 分子量: 407.556
• InChiKey: WDUAKIUNIHIRQB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.7
• 重原子数：
  18
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.08
• 拓扑面积：
  40.3
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  5-chloro-2-(2,2-dibromovinyl)-N-(3-thienylmethyl)aniline 在 tris-(dibenzylideneacetone)dipalladium(0) 、 三(2-甲氧基苯基)膦 、 caesium carbonate 、 silver carbonate 作用下， 以 甲苯 为溶剂， 以92%的产率得到7-chloro-4H-thieno[2',3':3,4]pyrrolo[1,2-a]indole
  参考文献：
  名称：

  Silver-Promoted Domino Pd-Catalyzed Amination/Direct Arylation: Access to Polycyclic Heteroaromatics

  摘要：

  Novel tetracyclic and pentacyclic indole derivatives can be prepared from readily available gem-dibromovinyl substrates in a single step by means of an efficient Pd-catalyzed domino Buchwald-Hartwig amination/direct arylation reaction. Enhanced reactivity and selectivity are obtained by the addition of silver salts.

  DOI：

  10.1021/ol801932z
• 作为产物：
  描述：

  3-噻吩甲醛 、 5-chloro-2-(2,2-dibromo-vinyl)-phenylamine 在 三乙酰氧基硼氢化钠 、 溶剂黄146 作用下， 以 1,2-二氯乙烷 为溶剂， 以84%的产率得到5-chloro-2-(2,2-dibromovinyl)-N-(3-thienylmethyl)aniline
  参考文献：
  名称：

  Silver-Promoted Domino Pd-Catalyzed Amination/Direct Arylation: Access to Polycyclic Heteroaromatics

  摘要：

  Novel tetracyclic and pentacyclic indole derivatives can be prepared from readily available gem-dibromovinyl substrates in a single step by means of an efficient Pd-catalyzed domino Buchwald-Hartwig amination/direct arylation reaction. Enhanced reactivity and selectivity are obtained by the addition of silver salts.

  DOI：

  10.1021/ol801932z

文献信息

• Silver-Promoted Domino Pd-Catalyzed Amination/Direct Arylation: Access to Polycyclic Heteroaromatics
  作者：Christopher S. Bryan、Mark Lautens

  DOI：10.1021/ol801932z

  日期：2008.10.16

  Novel tetracyclic and pentacyclic indole derivatives can be prepared from readily available gem-dibromovinyl substrates in a single step by means of an efficient Pd-catalyzed domino Buchwald-Hartwig amination/direct arylation reaction. Enhanced reactivity and selectivity are obtained by the addition of silver salts.