9-[2-(carboxyethyl)benzyl]-3,4-dimethyl-7,8-diethyl-dipyrrinone | 271580-28-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 四吡咯及其衍生物
• 英文名称: 9-[2-(carboxyethyl)benzyl]-3,4-dimethyl-7,8-diethyl-dipyrrinone
• 英文别名: hemirubin；3-[2-[[5-[(Z)-(3,4-dimethyl-5-oxopyrrol-2-ylidene)methyl]-3,4-diethyl-1H-pyrrol-2-yl]methyl]phenyl]propanoic acid
• CAS: 271580-28-0
• 化学式: C₂₅H₃₀N₂O₃
• 分子量: 406.525
• InChiKey: DAXWTNJLGIWWLH-STZFKDTASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.2
• 重原子数：
  30
• 可旋转键数：
  8
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  82.2
• 氢给体数：
  3
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  甲醇 、 9-[2-(carboxyethyl)benzyl]-3,4-dimethyl-7,8-diethyl-dipyrrinone 在 硫酸 作用下， 反应 1.0h， 以95%的产率得到9-[2-(methoxycarbonylethyl)benzyl]-3,4-dimethyl-7,8-diethyl-dipyrrinone
  参考文献：
  名称：

  Stereochemistry and Conformational Analysis of Hemirubin

  摘要：

  Intramolecularly hydrogen-bonded analogs of the natural bile pigment, bilirubin, are very scarce. Nuclear Overhauser effect NMR studies of the newest analog, a hemirubin (1), confirms intramolecular hydrogen bonding and a ridge-tile-shaped conformation. H-1 NMR studies of 1 at sufficiently low temperatures detect conformational enantiomerization, for which an activation barrier of Delta G(double dagger)similar to 16 kcal/mol at 25 degrees C in CDCl3 has been estimated. Evidence for the presence of dimeric association at low temperatures or high concentrations of 1 is found by the appearance of new sets of resonances, data from which may be used to calculate: Delta G degrees(298) (K) + 3.4 kca/mol, Delta H degrees - 5.6 kcal/mol and Delta S degrees -30.3 cal/deg/mol. (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(00)00087-9
• 作为产物：
  描述：

  2,3-dimethyl-7,8-diethyl-10H-dipyrrin-1-one-9-carboxylic acid 在 sodium hydroxide 、 sodium tetrahydroborate 、 potassium acetate 、 sodium acetate 、 四氯化锡 作用下， 以 四氢呋喃 、 二氯甲烷 、 水 、 异丙醇 为溶剂， 反应 9.67h， 生成 9-[2-(carboxyethyl)benzyl]-3,4-dimethyl-7,8-diethyl-dipyrrinone
  参考文献：
  名称：

  Stereochemistry and Conformational Analysis of Hemirubin

  摘要：

  Intramolecularly hydrogen-bonded analogs of the natural bile pigment, bilirubin, are very scarce. Nuclear Overhauser effect NMR studies of the newest analog, a hemirubin (1), confirms intramolecular hydrogen bonding and a ridge-tile-shaped conformation. H-1 NMR studies of 1 at sufficiently low temperatures detect conformational enantiomerization, for which an activation barrier of Delta G(double dagger)similar to 16 kcal/mol at 25 degrees C in CDCl3 has been estimated. Evidence for the presence of dimeric association at low temperatures or high concentrations of 1 is found by the appearance of new sets of resonances, data from which may be used to calculate: Delta G degrees(298) (K) + 3.4 kca/mol, Delta H degrees - 5.6 kcal/mol and Delta S degrees -30.3 cal/deg/mol. (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(00)00087-9