(4Z)-9-(5-carboxypentyl)-2,3-dimethyl-7,8-diethyl-(10H)-dipyrrin-1-one | 928624-59-3

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: (4Z)-9-(5-carboxypentyl)-2,3-dimethyl-7,8-diethyl-(10H)-dipyrrin-1-one
• CAS: 928624-59-3
• 化学式: C₂₁H₃₀N₂O₃
• 分子量: 358.481
• InChiKey: JKRZVIHWNSMXLE-PDGQHHTCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.13
• 重原子数：
  26.0
• 可旋转键数：
  9.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.52
• 拓扑面积：
  82.19
• 氢给体数：
  3.0
• 氢受体数：
  2.0

反应信息

• 作为反应物：
  描述：

  (4Z)-9-(5-carboxypentyl)-2,3-dimethyl-7,8-diethyl-(10H)-dipyrrin-1-one 、 叔丁胺 在 二苯基膦叠氮化物 、 三乙胺 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 72.0h， 以76%的产率得到(4Z)-9-(5-t-butylcarboxamidopentyl)-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)-7,8-diethyl-2,3-dimethyl-(9H)-dipyrrin-1-one 在 sodium hydroxide 、 sodium tetrahydroborate 、 三氯化铝 作用下， 以 四氢呋喃 、 二氯甲烷 、 水 、 异丙醇 为溶剂， 反应 22.67h， 生成 (4Z)-9-(5-carboxypentyl)-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