N,N-Dimethyl (Z)-3-iodopropenamide | 68596-67-8

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: N,N-Dimethyl (Z)-3-iodopropenamide
• 英文别名: cis-β-iodo-N,N-dimethylacrylamide；(Z)-3-iodo-N,N-dimethylprop-2-enamide
• CAS: 68596-67-8
• 化学式: C₅H₈INO
• 分子量: 225.029
• InChiKey: NHIBRNZJJDHQMY-ARJAWSKDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.8
• 重原子数：
  8
• 可旋转键数：
  1
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  20.3
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  N,N-Dimethyl (Z)-3-iodopropenamide 在 palladium diacetate 、 palladium dichloride 硼氘化钠 作用下， 以 乙腈 为溶剂， 反应 120.0h， 生成
  参考文献：
  名称：

  Palladium(II) mediated aziridination of olefins with bromamine-T as the nitrogen source: scope and mechanism

  摘要：

  The palladium(II)-promoted reaction of a variety of olefins and bromamine-T provided N-tosyl-2-substituted aziridines under mild conditions. Olefins bearing chiral appendages gave only a poor to modest diastereoselectivity. Appropriate deuterated olefins were selected to study the stereochemistry of the reaction. A Pd(IV) intermediate is proposed as the aziridinating species. (C) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2007.05.020
• 作为产物：
  描述：

  N,N-dimethylpropynamide 在 溶剂黄146 、 lithium iodide 作用下， 反应 24.0h， 以67%的产率得到N,N-Dimethyl (Z)-3-iodopropenamide
  参考文献：
  名称：

  A novel regio- and stereospecific hydrohalogenation reaction of 2-propynoic acid and its derivatives

  摘要：

  2-Propynoic acid and its derivatives are hydrohalogenated regio- and stereospecifically by reaction with lithium halides in acetic acid, or preferably with 1 equiv of acetic acid in refluxing CH3CN, to afford the thermodynamically unfavorable (Z)-3-halopropenoic acids and their derivatives as sole products. A rationale for the regio- and stereospecificity is briefly discussed.

  DOI：

  10.1021/jo00028a055