N-[(Z)-1-Butylcarbamoyl-2-((S)-2,2-dimethyl-[1,3]dioxolan-4-yl)-vinyl]-benzamide | 145531-78-8

• 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: N-[(Z)-1-Butylcarbamoyl-2-((S)-2,2-dimethyl-[1,3]dioxolan-4-yl)-vinyl]-benzamide
• 英文别名: N-[(Z)-3-(butylamino)-1-[(4S)-2,2-dimethyl-1,3-dioxolan-4-yl]-3-oxoprop-1-en-2-yl]benzamide
• CAS: 145531-78-8
• 化学式: C₁₉H₂₆N₂O₄
• 分子量: 346.426
• InChiKey: BJZBDTIRYNOOPL-JORMNFRLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  25
• 可旋转键数：
  7
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.47
• 拓扑面积：
  76.7
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  N-[(Z)-1-Butylcarbamoyl-2-((S)-2,2-dimethyl-[1,3]dioxolan-4-yl)-vinyl]-benzamide 在 N-溴代丁二酰亚胺(NBS) 、 三乙胺 作用下， 以 乙腈 为溶剂， 反应 24.0h， 生成 N-[(E)-2-Bromo-1-butylcarbamoyl-2-((R)-2,2-dimethyl-[1,3]dioxolan-4-yl)-vinyl]-benzamide
  参考文献：
  名称：

  Characterization of α-halo-imine intermediates derived from halogenation of dehydroamino acid derivatives

  摘要：

  An efficient one-pot Erlenmeyer-Plochl reaction affords high yields of optically active aliphatic dehydroamino acid derivatives. Subsequent halogenation with NBS or NIS yields the alpha-halo-imine derivatives which undergo kinetically controlled tautomerization with Et3N, resulting in increased E selectivity. Isomerization of these derivatives in the presence of strong base (DABCO) results in exclusive formation of the more stable Z vinyl bromides. High yields of the beta-halo-dehydroamino acids are obtained in all cases.

  DOI：

  10.1016/s0040-4039(00)79004-6
• 作为产物：
  描述：

  双丙酮-D-甘露糖醇 在 lead(IV) acetate 、 乙酸酐 作用下， 以 四氢呋喃 为溶剂， 反应 16.08h， 生成 N-[(Z)-1-Butylcarbamoyl-2-((S)-2,2-dimethyl-[1,3]dioxolan-4-yl)-vinyl]-benzamide
  参考文献：
  名称：

  Characterization of α-halo-imine intermediates derived from halogenation of dehydroamino acid derivatives

  摘要：

  An efficient one-pot Erlenmeyer-Plochl reaction affords high yields of optically active aliphatic dehydroamino acid derivatives. Subsequent halogenation with NBS or NIS yields the alpha-halo-imine derivatives which undergo kinetically controlled tautomerization with Et3N, resulting in increased E selectivity. Isomerization of these derivatives in the presence of strong base (DABCO) results in exclusive formation of the more stable Z vinyl bromides. High yields of the beta-halo-dehydroamino acids are obtained in all cases.

  DOI：

  10.1016/s0040-4039(00)79004-6