(4Z)-9-(5-carboxypentanoyl)-2,3-dimethyl-7,8-diethyl-(10H)-dipyrrin-1-one | 928624-62-8

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 酮酸及其衍生物
• 英文名称: (4Z)-9-(5-carboxypentanoyl)-2,3-dimethyl-7,8-diethyl-(10H)-dipyrrin-1-one
• CAS: 928624-62-8
• 化学式: C₂₁H₂₈N₂O₄
• 分子量: 372.464
• InChiKey: UJKJEWNOIHTHFP-WJDWOHSUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.77
• 重原子数：
  27.0
• 可旋转键数：
  9.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.48
• 拓扑面积：
  99.26
• 氢给体数：
  3.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  (4Z)-9-(5-carboxypentanoyl)-2,3-dimethyl-7,8-diethyl-(10H)-dipyrrin-1-one 在 sodium tetrahydroborate 、 二苯基膦叠氮化物 、 三乙胺 作用下， 以 N,N-二甲基甲酰胺 、 异丙醇 为溶剂， 反应 76.5h， 生成 (4Z)-9-(5-N,N-diethylcarboxamidopentyl)-2,3-dimethyl-7,8-diethyl-(10H)-dipyrrin-1-one
  参考文献：
  名称：

  Amide–Amide Hydrogen Bonding. Semirubin Amides

  摘要：

  Semirubins are analogs for one-half of the bilirubin structure and capable of intramolecular hydrogen bonding. Semirubin amides of ammonia and primary amines are also capable of intramolecular hydrogen bonding. From a combination of spectroscopic methods (H-1 NMR, NOE, and VPO), the primary amide is found to engage very effectively in intramolecular hydrogen bonding. The secondary and tertiary amides engage in both intramolecular (i) and intermolecular (ii) hydrogen bonding: N-methyl (i, monomer + ii, dimer), N-tert-butyl (ii, dimer), N,N-diethyl (i, monomer + ii, dimer). With an oxo-group at C(10), all of the amides are monomeric and most engage in intramolecular hydrogen bonding.

  DOI：

  10.1007/s00706-005-0433-5
• 作为产物：
  描述：

  (4Z)-9-(5-carboethoxypentanoyl)-2,3-dimethyl-7,8-diethyl-(10H)-dipyrrin-1-one 在 sodium hydroxide 作用下， 以 四氢呋喃 、 水 为溶剂， 反应 3.0h， 以89%的产率得到(4Z)-9-(5-carboxypentanoyl)-2,3-dimethyl-7,8-diethyl-(10H)-dipyrrin-1-one
  参考文献：
  名称：

  Amide–Amide Hydrogen Bonding. Semirubin Amides

  摘要：

  Semirubins are analogs for one-half of the bilirubin structure and capable of intramolecular hydrogen bonding. Semirubin amides of ammonia and primary amines are also capable of intramolecular hydrogen bonding. From a combination of spectroscopic methods (H-1 NMR, NOE, and VPO), the primary amide is found to engage very effectively in intramolecular hydrogen bonding. The secondary and tertiary amides engage in both intramolecular (i) and intermolecular (ii) hydrogen bonding: N-methyl (i, monomer + ii, dimer), N-tert-butyl (ii, dimer), N,N-diethyl (i, monomer + ii, dimer). With an oxo-group at C(10), all of the amides are monomeric and most engage in intramolecular hydrogen bonding.

  DOI：

  10.1007/s00706-005-0433-5