N-(diphenylmethylene)-2-phenylethynamine | 110027-83-3

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 直链 1,3-二芳基丙烷
• 英文名称: N-(diphenylmethylene)-2-phenylethynamine
• 英文别名: 1,1-diphenyl-N-(phenylethynyl)methanimine；1,1-diphenyl-N-(2-phenylethynyl)methanimine
• CAS: 110027-83-3
• 化学式: C₂₁H₁₅N
• 分子量: 281.357
• InChiKey: BLHWGLSRSCCTDD-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.7
• 重原子数：
  22
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  12.4
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为产物：
  描述：

  benzophenone O-acetyl oxime 、 苯乙炔 在 2,2'-联喹啉 、 copper diacetate 、 potassium carbonate 作用下， 以 1,2-二氯乙烷 为溶剂， 反应 44.0h， 以45%的产率得到N-(diphenylmethylene)-2-phenylethynamine
  参考文献：
  名称：

  Copper‐Catalyzed Aza‐Sonogashira Cross‐Coupling To Form Ynimines: Development and Application to the Synthesis of Heterocycles

  摘要：

  AbstractNitrogen‐substituted alkynes, such as ynamines and ynamides, are versatile synthetic building blocks. Ynimines bearing additional nucleophilic and electrophilic centers relative to ynamines and ynamides are expected to have high synthetic potential. However, their chemical reactivity remains unexplored owing mainly to the lack of synthetic accessibility. We report herein a versatile copper‐catalyzed synthesis of ynimines from readily available O‐acetyl ketoximes and terminal alkynes. A wide range of O‐acetyl ketoximes derived from diaryl ketones, aryl alkyl ketones and dialkyl ketones underwent cross‐coupling with a diverse set of terminal alkynes to afford the ynimines in good to excellent yields. An unprecedented [5+1] heteroannulation reaction exploiting the reactivity of the ynimine generated in situ was subsequently developed for the synthesis of medicinally important heterocycles, including isoquinolines, azaindoles, azabenzofurans, azabenzothiophenes and carbolines.

  DOI：

  10.1002/anie.202110901

文献信息

• Copper-Catalyzed Oxidative Alkynylation of Diaryl Imines with Terminal Alkynes: A Facile Synthesis of Ynimines
  作者：Anouar Laouiti、Mohamed M. Rammah、Mohamed B. Rammah、Jérome Marrot、François Couty、Gwilherm Evano

  DOI：10.1021/ol2032152

  日期：2012.1.6

  An efficient copper-mediated method for the oxidative alkynylation of diaryl imines with terminal alkynes is reported. This reaction provides the first catalytic and general synthesis of ynimines and allows for an easy preparation of these useful building blocks. An improved copper-catalyzed oxidative dimerization of imines to azines and the synthesis of dienes and azadienes from ynimines are also

  报道了一种有效的铜介导的方法，用于将二芳基亚胺与末端炔烃进行氧化炔基反应。该反应提供了亚胺的第一催化和一般合成，并允许容易地制备这些有用的结构单元。还描述了改进的铜催化的亚胺向嗪的氧化二聚反应以及由二亚胺合成二烯和氮杂二烯的方法。
• Wuerthwein, Ernst-Ulrich; Weigmann, Reinhard, Angewandte Chemie, 1987, vol. 99, # 9, p. 918 - 919
  作者：Wuerthwein, Ernst-Ulrich、Weigmann, Reinhard

  DOI：——

  日期：——