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 | 79719-28-1

• 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: 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
• 英文别名: mesobilirubin-XIIIα；3-[2-[[3-(2-carboxyethyl)-5-[(Z)-(3-ethyl-4-methyl-5-oxopyrrol-2-ylidene)methyl]-4-methyl-1H-pyrrol-2-yl]methyl]-5-[(Z)-(3-ethyl-4-methyl-5-oxopyrrol-2-ylidene)methyl]-4-methyl-1H-pyrrol-3-yl]propanoic acid
• CAS: 79719-28-1
• 化学式: C₃₃H₄₀N₄O₆
• 分子量: 588.704
• InChiKey: PSUYEWBLPHMDMK-IFADSCNNSA-N

物化性质

• 沸点：
  900.9±65.0 °C(Predicted)
• 密度：
  1.283±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  43
• 可旋转键数：
  12
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.39
• 拓扑面积：
  164
• 氢给体数：
  6
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  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 在 ammonium hydroxide 作用下， 以 甲醇 为溶剂， 生成 (4Z,15E)-mesobilirubin XIIIα
  参考文献：
  名称：

  Induction of Wavelength-Dependent Photochemistry in Bilirubins by Serum Albumin

  摘要：

  DOI：

  10.1007/pl00013473
• 作为产物：
  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

文献信息

• Trull, Francesc R.; Lightner, David A., Journal of Heterocyclic Chemistry, 1988, vol. 25, p. 1227 - 1230
  作者：Trull, Francesc R.、Lightner, David A.

  DOI：——

  日期：——
• On the preparation of bilirubins of the natural ? series substituted with a propionic acid residue and a hydroxypropyl group
  作者：J. Crusats、J. -A. Farrera、J. M. Rib�

  DOI：10.1007/bf00807412

  日期：1996.1

  The reduction of mesobiliverdin XIII alpha propan-1,3-diyl diester with NaBH4 affords mesobilirubin XIII alpha propan-1,3-diyl diester. The same reduction of mesobiliverdin XIII alpha methylen diester. The same reduction of mesobiliverdin XIII alpha methylen diester affords 8-(2-carboxyethyl)-3,17-diethyl-12-(3-hydroxypropyl)-2,7,13,17-tetramethylbiladien-ac-1,19-(21H, 24H)-dione (MBR-mc). The UV/Vis and H-1 NMR spectra of MBR-mc show that its structure in solution is similar to that of the natural bilirubins of the a series.
• TRULL, FRANCESC R.;FRANKLIN, ROGER W.;LIGHTNER, DAVID A., J. HETEROCYCL. CHEM., 24,(1987) N 6, 1573-1579
  作者：TRULL, FRANCESC R.、FRANKLIN, ROGER W.、LIGHTNER, DAVID A.

  DOI：——

  日期：——
• TRULL, FRANCESC R.;LIGHTNER, DAVID A., J. HETEROCYCL. CHEM., 25,(1988) N 4, C. 1227-1230
  作者：TRULL, FRANCESC R.、LIGHTNER, DAVID A.

  DOI：——

  日期：——
• 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%。