mesobilirubin-XIIIα dimethyl ester | 89332-47-8

• 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: mesobilirubin-XIIIα dimethyl ester
• 英文别名: methyl 3-[5-[(Z)-(3-ethyl-4-methyl-5-oxopyrrol-2-ylidene)methyl]-2-[[5-[(Z)-(3-ethyl-4-methyl-5-oxopyrrol-2-ylidene)methyl]-3-(3-methoxy-3-oxopropyl)-4-methyl-1H-pyrrol-2-yl]methyl]-4-methyl-1H-pyrrol-3-yl]propanoate
• CAS: 89332-47-8
• 化学式: C₃₅H₄₄N₄O₆
• 分子量: 616.758
• InChiKey: MEFHNFPTBBKFQS-FLZZTMJYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  45
• 可旋转键数：
  14
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  142
• 氢给体数：
  4
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  mesobilirubin-XIIIα dimethyl ester 在 sodium hydroxide 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 反应 4.0h， 以97%的产率得到3-{2-{3-(2-Carboxy-ethyl)-5-[3-ethyl-4-methyl-5-oxo-1,5-dihydro-pyrrol-(2Z)-ylidenemethyl]-4-methyl-1H-pyrrol-2-ylmethyl}-5-[3-ethyl-4-methyl-5-oxo-1,5-dihydro-pyrrol-(2Z)-ylidenemethyl]-4-methyl-1H-pyrrol-3-yl}-propionic acid
  参考文献：
  名称：

  An Efficient Synthesis of Symmetric Bilindiones. Mesobilirubin-Xlllα and Analogs with Varying Alkanoic Acid Chain Lengths

  摘要：

  本文介绍了一种成本低廉的克级三步法，可将黄原胆红素甲酯及其烷酸酯类似物（5-[(3-乙基-1, 5-二氢-4-甲基-5-氧代-2H-吡咯-2-亚基)甲基]-1, 4-二甲基吡咯-3-乙酸酯、-丙酸酯、-丁酸酯、-戊酸酯、-己酸酯）转化为中黄原胆红素-XIIIδ和类似物，每一步的收率均大于 90%。

  DOI：

  10.1055/s-1992-26102
• 作为产物：
  描述：

  mesobiliverdin XIIIα dimethylester 在 sodium tetrahydroborate 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 以92%的产率得到mesobilirubin-XIIIα dimethyl ester
  参考文献：
  名称：

  An Efficient Synthesis of Symmetric Bilindiones. Mesobilirubin-Xlllα and Analogs with Varying Alkanoic Acid Chain Lengths

  摘要：

  本文介绍了一种成本低廉的克级三步法，可将黄原胆红素甲酯及其烷酸酯类似物（5-[(3-乙基-1, 5-二氢-4-甲基-5-氧代-2H-吡咯-2-亚基)甲基]-1, 4-二甲基吡咯-3-乙酸酯、-丙酸酯、-丁酸酯、-戊酸酯、-己酸酯）转化为中黄原胆红素-XIIIδ和类似物，每一步的收率均大于 90%。

  DOI：

  10.1055/s-1992-26102

文献信息

• Synthesis and properties of bilirubin analogs with N,N-methylene bridges
  作者：Ki-Oh Hwang、D.Timothy Anstine、David A. Lightner

  DOI：10.1016/s0040-4020(01)89607-1

  日期：1994.1

  Bilirubin analogs have been prepared with a methylene group forming an N to N bridge. When the bridge is in the same dipyrrinone, only one propionic acid can hydrogen bond intramolecularly (to the unbridged dipyrrinone), but the pigment still adopts a ridge-tile conformation. Molecular dynamics calculations predict global energy minima for two enantiomeric ridge-tile conformations separated by an energy barrier of similar to 14.5 kcal/mole. In contrast, when the bridge connects two dipyrrinones through their lactam nitrogens, that pigment is held in a porphyrin-like shape, neither propionic acid groups can participate in intramolecular hydrogen bonding, and the pigment is much more polar and hydrophilic than bilirubin. Molecular dynamics calculations predict an interconversion barrier of similar to 25 kcal/mole for this isomer.
• A novel 16,24-dehydrobiladiene-ab system: The reaction of xanthobilirubic acid methyl ester with bromine
  作者：J. -S. Ma、Q. -Q. Chen、C. -Q. Wang、Y. -Y. Liu、F. Yan、L. -J. Cheng、S. Jin、H. Falk

  DOI：10.1007/bf00812248

  日期：1995.2

  On treating xanthobilirubic acid methyl ester with bromine in methanol, a red bile pigment, which was assigned the hitherto unknown 16,24-dehydrobiladiene-ab constitution, is obtained in 20% yield. In addition, the corresponding mesobiliverdin-XIII alpha, mesobilirubin-XIII alpha, 14-formyl-tripyrrinone, and two diastereomeric 15,16-dimethoxybiladienes-ab could be isolated from the reaction mixture. The mechanistic aspects of this reaction are discussed.
• An Efficient Synthesis of Symmetric Bilindiones. Mesobilirubin-Xlllα and Analogs with Varying Alkanoic Acid Chain Lengths
  作者：David P. Shrout、Gisbert Puzicha、David A. Lightner

  DOI：10.1055/s-1992-26102

  日期：——

  An inexpensive gram-scale, three-step procedure is described to convert methyl xanthobilirubinate and it alkanoic acid ester analogs (methyl 5-[(3-ethyl-1, 5-dihydro-4-methyl-5-oxo-2H-pyrrol-2-ylidene)methyl]-1, 4-dimethylpyrrol-3-ethanoate, -propanoate, -butanoate, -pentanoate, -hexanoate) into mesobilirubin-XIIIα and analogs in > 90% yield at each step.

  本文介绍了一种成本低廉的克级三步法，可将黄原胆红素甲酯及其烷酸酯类似物（5-[(3-乙基-1, 5-二氢-4-甲基-5-氧代-2H-吡咯-2-亚基)甲基]-1, 4-二甲基吡咯-3-乙酸酯、-丙酸酯、-丁酸酯、-戊酸酯、-己酸酯）转化为中黄原胆红素-XIIIδ和类似物，每一步的收率均大于 90%。