2-[(dimethylamino)methylene]-N¹,N³-diphenylmalonamide

• 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-[(dimethylamino)methylene]-N¹,N³-diphenylmalonamide
• 英文别名: 2-[(dimethylamino)methylene]-N~1~,N~3~-diphenylmalonamide；2-(dimethylaminomethylidene)-N,N'-diphenylpropanediamide
• 化学式: C₁₈H₁₉N₃O₂
• 分子量: 309.368
• InChiKey: UYIZNXAWOLXLJU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  23
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.11
• 拓扑面积：
  61.4
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2-[(dimethylamino)methylene]-N¹,N³-diphenylmalonamide 在 ammonium hydroxide 作用下， 以 乙醇 为溶剂， 以60%的产率得到2-(aminomethylene)-N¹,N³-diphenylmalonamide
  参考文献：
  名称：

  Oxidative Cyclization of β-Aminoacrylamides Mediated by PhIO: Chemoselective Synthesis of Isoxazoles and 2H-Azirines

  摘要：

  Cyclization of a variety of beta-aminoacrylamides in the presence of iodosobenzene (PhIO) is described. This process features mild reaction conditions, simple execution, and high chemoselectivity and thereby provides an efficient protocol for the divergent synthesis of substituted isoxazoles and 2H-azirines via switchable N-O and N-C bond formation controlled by simply varying the beta-substituent R-3 of the readily available substrates.

  DOI：

  10.1021/acs.joc.8b02132

文献信息

• Formal [4+2] annulation of enaminones and cyanomethyl sulfur ylide: one-pot access to polysubstituted pyridin-2(1H)-ones
  作者：Qian Zhang、Xu Liu、Xiaoqing Xin、Rui Zhang、Yongjiu Liang、Dewen Dong

  DOI：10.1039/c4cc06665k

  日期：——

  A facile and efficient one-pot synthesis of polysubstituted pyridin-2(1H)-ones from readily available enaminones and the cyanomethyl sulfonium bromide salt in the presence of cesium carbonate is developed, and a mechanism involving sequential nucleophilic vinylic substitution (S(N)V), intramolecular nucleophilic cyclization and dealkylation reactions is proposed.

  研究了在碳酸铯存在下，由现成的烯胺酮和氰基甲基溴化salt盐容易，高效地一锅合成多取代的吡啶-2（1H）-酮的方法，并且涉及到一种连续亲核乙烯基取代（S（N） V），提出了分子内亲核环化和脱烷基反应。
• Oxidative Cyclization of β-Aminoacrylamides Mediated by PhIO: Chemoselective Synthesis of Isoxazoles and 2<i>H</i>-Azirines
  作者：Chaoran Li、Jingwen Yuan、Qian Zhang、Chitturi Bhujanga Rao、Rui Zhang、Yanning Zhao、Bicheng Deng、Dewen Dong

  DOI：10.1021/acs.joc.8b02132

  日期：2018.12.21

  Cyclization of a variety of beta-aminoacrylamides in the presence of iodosobenzene (PhIO) is described. This process features mild reaction conditions, simple execution, and high chemoselectivity and thereby provides an efficient protocol for the divergent synthesis of substituted isoxazoles and 2H-azirines via switchable N-O and N-C bond formation controlled by simply varying the beta-substituent R-3 of the readily available substrates.