diethyl (Z)-2-(ethoxycarbonyl)-2-formamido-4-chloro-6-amino-3-heptene-1,7-dioate | 100910-54-1

• 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: diethyl (Z)-2-(ethoxycarbonyl)-2-formamido-4-chloro-6-amino-3-heptene-1,7-dioate
• CAS: 100910-54-1
• 化学式: C₁₅H₂₃ClN₂O₇
• 分子量: 378.81
• InChiKey: USKNZKBUOFSTPJ-NTMALXAHSA-N

物化性质

• 沸点：
  537.1±50.0 °C(Predicted)
• 密度：
  1?+-.0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.0
• 重原子数：
  25.0
• 可旋转键数：
  11.0
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.6
• 拓扑面积：
  134.02
• 氢给体数：
  2.0
• 氢受体数：
  8.0

反应信息

• 作为反应物：
  描述：

  diethyl (Z)-2-(ethoxycarbonyl)-2-formamido-4-chloro-6-amino-3-heptene-1,7-dioate 在 盐酸 作用下， 反应 5.0h， 以65%的产率得到(z)-2,6-diamino-4-chloro-3-heptene-1,7-dioic acid dihydrochloride
  参考文献：
  名称：

  The lysine pathway as a target for a new genera of synthetic antibacterial antibiotics?

  摘要：

  Unsaturated analogues of diaminopimelic acid have been synthesized. The amino acids were designed so that they would be reversible or irreversible inhibitors of both of the two last enzymes of the lysine pathway. The compounds were tested with meso-diaminopimelate decarboxylase. trans-3,4-Didehydrodiaminopimelic acid (2) was found to be the most potent inhibitor. The antibacterial activities did not correlate with enzyme inhibiting activities. 4-Methylenediaminopimelic acid 4 showed strong antibacterial properties. It is suggested that L,L-diaminopimelate epimerase could be the target enzyme.

  DOI：

  10.1021/jm00156a021
• 作为产物：
  描述：

  (Z)-4-Chloro-2-ethoxycarbonyl-2-formylamino-6-hydroxy-hept-3-enedioic acid diethyl ester 在 Lindlar's catalyst 吡啶 、 sodium azide 、 氢气 作用下， 以 乙醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 32.0h， 生成 diethyl (Z)-2-(ethoxycarbonyl)-2-formamido-4-chloro-6-amino-3-heptene-1,7-dioate
  参考文献：
  名称：

  The lysine pathway as a target for a new genera of synthetic antibacterial antibiotics?

  摘要：

  Unsaturated analogues of diaminopimelic acid have been synthesized. The amino acids were designed so that they would be reversible or irreversible inhibitors of both of the two last enzymes of the lysine pathway. The compounds were tested with meso-diaminopimelate decarboxylase. trans-3,4-Didehydrodiaminopimelic acid (2) was found to be the most potent inhibitor. The antibacterial activities did not correlate with enzyme inhibiting activities. 4-Methylenediaminopimelic acid 4 showed strong antibacterial properties. It is suggested that L,L-diaminopimelate epimerase could be the target enzyme.

  DOI：

  10.1021/jm00156a021