N,1-dimethylpyrrole-3-carboxamide | 1235479-01-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯
• 英文名称: N,1-dimethylpyrrole-3-carboxamide
• CAS: 1235479-01-2
• 化学式: C₇H₁₀N₂O
• mdl: MFCD19227748
• 分子量: 138.169
• InChiKey: YZJDHOMVQYEAPY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.1
• 重原子数：
  10
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.285
• 拓扑面积：
  34
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  N,1-dimethylpyrrole-3-carboxamide 、 二苯基乙炔 在 dichloro(pentamethylcyclopentadienyl)rhodium (III) dimer 、 copper diacetate 作用下， 以 2-甲基-2-丁醇 为溶剂， 反应 16.0h， 以63%的产率得到1,5-dimethyl-6,7-diphenyl-1H-pyrrolo[3,2-c]pyridin-4(5H)-one
  参考文献：
  名称：

  Rhodium-Catalyzed Oxidative Cycloaddition of Benzamides and Alkynes via C−H/N−H Activation

  摘要：

  The oxidative cycloaddition of benzamides and alkynes has been developed. The reaction utilizes Rh(III) catalysts in the presence of Cu(II) oxidants, and is proposed to proceed by N-H metalation of the amide followed by ortho C-H activation. The resultant rhodacycle undergoes alkyne insertion to form isoquinolones in good yield. The reaction is tolerant of extensive substitution on the amide, alkyne, and arene, including halides, silyl ethers, and unprotected aldehydes as substituents. Unsymmetrical alkynes proceed with excellent regioselectivity, and heteroaryl carboxamides are tolerated leading to intriguing scaffolds for medicinal chemistry. A series of competition experiments shed further light on the mechanism of the transformation and reasons for selectivity.

  DOI：

  10.1021/ja103776u
• 作为产物：
  描述：

  盐酸甲胺 、 1-甲基-1H-吡咯-3-羧酸 在 1-羟基苯并三唑 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 、 三乙胺 作用下， 以 乙腈 为溶剂， 反应 1.58h， 生成 N,1-dimethylpyrrole-3-carboxamide
  参考文献：
  名称：

  Rhodium-Catalyzed Oxidative Cycloaddition of Benzamides and Alkynes via C−H/N−H Activation

  摘要：

  The oxidative cycloaddition of benzamides and alkynes has been developed. The reaction utilizes Rh(III) catalysts in the presence of Cu(II) oxidants, and is proposed to proceed by N-H metalation of the amide followed by ortho C-H activation. The resultant rhodacycle undergoes alkyne insertion to form isoquinolones in good yield. The reaction is tolerant of extensive substitution on the amide, alkyne, and arene, including halides, silyl ethers, and unprotected aldehydes as substituents. Unsymmetrical alkynes proceed with excellent regioselectivity, and heteroaryl carboxamides are tolerated leading to intriguing scaffolds for medicinal chemistry. A series of competition experiments shed further light on the mechanism of the transformation and reasons for selectivity.

  DOI：

  10.1021/ja103776u