5-fluoro-2-(2-naphthyl)-indole | 1188178-22-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 5-fluoro-2-(2-naphthyl)-indole
• 英文别名: 5-fluoro-2-naphthalen-2-yl-1H-indole
• CAS: 1188178-22-4
• 化学式: C₁₈H₁₂FN
• 分子量: 261.298
• InChiKey: DJIROEFJMICZBW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.1
• 重原子数：
  20
• 可旋转键数：
  1
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  15.8
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为产物：
  描述：

  在 [Pd(IPr*)(cin)Cl] 、 sodium t-butanolate 作用下， 以 1,4-二氧六环 为溶剂， 反应 24.0h， 生成 5-fluoro-2-(2-naphthyl)-indole
  参考文献：
  名称：

  Catalytic α-Arylation of Imines Leading to N-Unprotected Indoles and Azaindoles

  摘要：

  A palladium N-heterocyclic carbene catalyzed methodology for the synthesis of substituted, N-unprotected indoles and azaindoles is reported. The protocol permits access to various, highly substituted members of these classes of compounds. Although two possible reaction pathways (deprotonative and Heck-like) can be proposed, control experiments, supported by computational studies, point toward a deprotonative mechanism being operative.

  DOI：

  10.1021/acscatal.6b00040

文献信息

• US4582848A
  申请人：——

  公开号：US4582848A

  公开（公告）日：1986-04-15
• Catalytic α-Arylation of Imines Leading to N-Unprotected Indoles and Azaindoles
  作者：Enrico Marelli、Martin Corpet、Yury Minenkov、Rifahath M. Neyyappadath、Alessandro Bismuto、Giulia Buccolini、Massimiliano Curcio、Luigi Cavallo、Steven P. Nolan

  DOI：10.1021/acscatal.6b00040

  日期：2016.5.6

  A palladium N-heterocyclic carbene catalyzed methodology for the synthesis of substituted, N-unprotected indoles and azaindoles is reported. The protocol permits access to various, highly substituted members of these classes of compounds. Although two possible reaction pathways (deprotonative and Heck-like) can be proposed, control experiments, supported by computational studies, point toward a deprotonative mechanism being operative.