2,3,7,8-tetramethyl-(10H)-dipyrrin-1-one-9-carboxylic acid | 92256-26-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯
• 英文名称: 2,3,7,8-tetramethyl-(10H)-dipyrrin-1-one-9-carboxylic acid
• 英文别名: 5-[(Z)-(3,4-dimethyl-5-oxopyrrol-2-ylidene)methyl]-3,4-dimethyl-1H-pyrrole-2-carboxylic acid
• CAS: 92256-26-3
• 化学式: C₁₄H₁₆N₂O₃
• 分子量: 260.293
• InChiKey: ZXFPXISPMKBMCD-WZUFQYTHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  19
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.29
• 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：

  trans-1,2-cyclohexandiol 、 2,3,7,8-tetramethyl-(10H)-dipyrrin-1-one-9-carboxylic acid 在 4 A molecular sieve 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 、 N,N'-羰基二咪唑 作用下， 生成 (1R,2R)-trans-cyclohexanediol mono<2,3,7,8-tetramethyl-(10H)-dipyrrin-1-one-9-carboxylate>
  参考文献：
  名称：

  Exciton coupling from dipyrrinone chromophores

  摘要：

  2,3,7,8-Tetramethyl-(10H)-dipyrrin-1-one-9-carboxylic acid and p-(dimethylamino)benzoic acid are reacted separately with (1R,2R)-cyclohexanediol to form the corresponding diesters (1 and 3, respectively). These diesters exhibit intense bisignate circular dichroism (CD) spectra characteristic of exciton coupling and show a negative exciton chirality: DELTA-epsilon-408max-122.5, DELTA-epsilon-360max+95 (1 in CH2Cl2) and DELTA-epsilon-318max-88.5, DELTA-epsilon-292max+41.5 (3 in CH2Cl2). In (CH3)2SO solvent the Cotton effect signs become inverted for the bis(dipyrrinone ester) but remain unchanged for the bis[p-(dimethylamino)benzoate ester].

  DOI：

  10.1021/jo00021a013
• 作为产物：
  描述：

  3,4-二甲基-1H-吡咯-2-羧酸 在 sodium hydroxide 、 双氧水 作用下， 以 吡啶 、 甲醇 为溶剂， 反应 1.67h， 生成 2,3,7,8-tetramethyl-(10H)-dipyrrin-1-one-9-carboxylic acid
  参考文献：
  名称：

  Exciton coupling from dipyrrinone chromophores

  摘要：

  2,3,7,8-Tetramethyl-(10H)-dipyrrin-1-one-9-carboxylic acid and p-(dimethylamino)benzoic acid are reacted separately with (1R,2R)-cyclohexanediol to form the corresponding diesters (1 and 3, respectively). These diesters exhibit intense bisignate circular dichroism (CD) spectra characteristic of exciton coupling and show a negative exciton chirality: DELTA-epsilon-408max-122.5, DELTA-epsilon-360max+95 (1 in CH2Cl2) and DELTA-epsilon-318max-88.5, DELTA-epsilon-292max+41.5 (3 in CH2Cl2). In (CH3)2SO solvent the Cotton effect signs become inverted for the bis(dipyrrinone ester) but remain unchanged for the bis[p-(dimethylamino)benzoate ester].

  DOI：

  10.1021/jo00021a013