3-(2-Carboxy-ethyl)-5-[3,4-dimethyl-5-oxo-1,5-dihydro-pyrrol-(2Z)-ylidenemethyl]-4-methyl-1H-pyrrole-2-carboxylic acid | 207803-87-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯
• 英文名称: 3-(2-Carboxy-ethyl)-5-[3,4-dimethyl-5-oxo-1,5-dihydro-pyrrol-(2Z)-ylidenemethyl]-4-methyl-1H-pyrrole-2-carboxylic acid
• CAS: 207803-87-0
• 化学式: C₁₆H₁₈N₂O₅
• 分子量: 318.329
• InChiKey: JLSHBXRFOLGXJM-WDZFZDKYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.85
• 重原子数：
  23.0
• 可旋转键数：
  5.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  119.49
• 氢给体数：
  4.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  3-(2-Carboxy-ethyl)-5-[3,4-dimethyl-5-oxo-1,5-dihydro-pyrrol-(2Z)-ylidenemethyl]-4-methyl-1H-pyrrole-2-carboxylic acid 在 potassium acetate 、 sodium acetate 、 caesium carbonate 、 三氟乙酸 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 8.33h， 生成 10-isopropyl-8,12-bis(2-methoxycarbonylethyl)-2,3,7,13,17,18-hexamethyl-1,10,19,21,23,24-hexahydro-1,19-dioxobilin
  参考文献：
  名称：

  Synthesis and properties of C(10) isopropyl and isopropylidene analogs of bilirubin

  摘要：

  Analogs of bilirubin with isopropyl (1) and isopropylidene (2) groups attached to the central C(10) carbon were synthesized and evaluated by a combination of NMR, UV-vis and circular dichroism spectroscopy and molecular dynamics calculations. These methods and H-1{H-1}-homonuclear Overhauser effect (NOE) experiments in CDCl3 solutions indicate that the rubins' carboxylic acid groups are tethered to the dipyrrinone lactams and/or pyrroles by intramolecular hydrogen bonds and confirm that the pigments adopt a folded, ridge-tile shape in solution. (C) 1998 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(98)00254-3
• 作为产物：
  描述：

  ethyl 4,5-dimethyl-3-(2-ethoxycarbonylethyl)pyrrole-2-carboxylate 在 氢氧化钾 、 ammonium cerium(IV) nitrate 作用下， 以 四氢呋喃 、 乙醇 、 水 、 溶剂黄146 为溶剂， 反应 1.0h， 生成 3-(2-Carboxy-ethyl)-5-[3,4-dimethyl-5-oxo-1,5-dihydro-pyrrol-(2Z)-ylidenemethyl]-4-methyl-1H-pyrrole-2-carboxylic acid
  参考文献：
  名称：

  Synthesis and properties of C(10) isopropyl and isopropylidene analogs of bilirubin

  摘要：

  Analogs of bilirubin with isopropyl (1) and isopropylidene (2) groups attached to the central C(10) carbon were synthesized and evaluated by a combination of NMR, UV-vis and circular dichroism spectroscopy and molecular dynamics calculations. These methods and H-1{H-1}-homonuclear Overhauser effect (NOE) experiments in CDCl3 solutions indicate that the rubins' carboxylic acid groups are tethered to the dipyrrinone lactams and/or pyrroles by intramolecular hydrogen bonds and confirm that the pigments adopt a folded, ridge-tile shape in solution. (C) 1998 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(98)00254-3