1H-吡咯-3-丙酸,5-[(Z)-(3,4-二乙基-1,5-二氢-5-羰基-2H-吡咯-2-亚基)甲基]-4-甲基- | 148317-91-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯
• 中文名称: 1H-吡咯-3-丙酸,5-[(Z)-(3,4-二乙基-1,5-二氢-5-羰基-2H-吡咯-2-亚基)甲基]-4-甲基-
• 英文名称: 2-ethyl-neoxanthobilirubic acid
• 英文别名: 2-ethylxanthobilirubic acid；3-ethylneoxanthobilirubic acid；3-[5-[(Z)-(3,4-diethyl-5-oxopyrrol-2-ylidene)methyl]-4-methyl-1H-pyrrol-3-yl]propanoic acid
• CAS: 148317-91-3
• 化学式: C₁₇H₂₂N₂O₃
• 分子量: 302.373
• InChiKey: HVHUUCNXFNLNPF-NVNXTCNLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  22
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.41
• 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：

  1H-吡咯-3-丙酸,5-[(Z)-(3,4-二乙基-1,5-二氢-5-羰基-2H-吡咯-2-亚基)甲基]-4-甲基- 在 二氯化硫 作用下， 以 二氯甲烷 为溶剂， 反应 6.0h， 以60%的产率得到(4Z,15Z)-8,12-bis(2-carboxyethyl)-7,13-dimethyl-2,3,17,18-tetraethyl-10-thia-(21H,23H,24H)-1,19-dioxobilin
  参考文献：
  名称：

  Synthesis and Metabolism of the First Thia-Bilirubin

  摘要：

  A symmetrical C(10)-thiabilirubin analogue, 8,12-bis(2-carboxyethyl)-2,3,17,18-tetraethyl-7,13-dimethyl-10-thia-(21H,23H,24H)-bilin-1,19-dione (1), was synthesized from 8-(2-carboxyethyl)-2,3-diethyl-7-methyl-10H-dipyrrin-1-one in one step by reaction with sulfur dichloride. The thia-rubin exhibited the expected IR, W-vis, and NMR spectroscopic properties, which are rather similar to those of mesobilirubin-XIII alpha. Like bilirubin and mesobilirubin, 1 adopts an intramolecularly hydrogen-bonded conformation, shaped like a ridge-tile but with a steeper pitch. The longer C-S bond lengths and smaller bond angles at C-S-C, as compared to C-CH2-C, lead to an interplanar angle between the two dipyrrinones of only 74 degrees -or considerably less than that of bilirubin (similar to 100 degrees). On normal- and reversed-phase chromatography, 1 is substantially less polar than bilirubin. Despite this conformational distortion, 1 is metabolized in normal rats to acyl glucuronides, which are secreted into bile. In mutant (Gunn) rats lacking bilirubin glucuronosyl transferase, 1 (like bilirubin) was not excreted in bile.

  DOI：

  10.1021/jo001598w
• 作为产物：
  描述：

  4-methyl-2,5-dicarboxy-1H-pyrrole-3-propanoic acid 在 氢氧化钾 、 sodium hydroxide 、 三氟乙酸 、 三氯氧磷 作用下， 以 甲醇 、 乙醚 、 水 为溶剂， 25.0~180.0 ℃ 、266.64 Pa 条件下， 反应 53.5h， 生成 1H-吡咯-3-丙酸,5-[(Z)-(3,4-二乙基-1,5-二氢-5-羰基-2H-吡咯-2-亚基)甲基]-4-甲基-
  参考文献：
  名称：

  Synthesis and unusual properties of C-(10)-gem-dimethyl bilirubin analogs

  摘要：

  The characteristic thermodynamically-favored intramolecularly hydrogen-bonded conformation adopted by bilirubin pigments is destabilized by substituting methyl groups on the C(10) central methylene. These methyl groups impose conformation-destabilizing methyl-methylene non-bonded steric interactions with the propionic acid beta-CH2 groups at C(8) and C(12) when the propionic acids are engaged in intramolecular hydrogen bonding with the opposing dipyrrinones. Amphiphilic 10,10-dimethylbilirubins (1) and (2) are found to be more polar, but also more soluble than the parents (3) and (4) in organic solvents; yet, H-1-NMR studies in non-polar solvents indicate that a deformed but folded, intramolecularly hydrogen-bonded conformation is retained. The dimethyl esters of 10,10-dimethylbilirubins 1 and 2 did not exhibit the typical strong tendency of bilirubin dimethyl esters to form intermolecular hydrogen bonds in non-polar solvents such as chloroform and benzene.

  DOI：

  10.1016/s0040-4020(01)80362-8

文献信息

• Synthesis, Conformation, and Metabolism of a Selenium Bilirubin
  作者：Brahmananda Ghosh、David A. Lightner、Antony F. McDonagh

  DOI：10.1007/s00706-004-0191-9

  日期：2004.9

  hydrogen-bonded conformation, shaped like a ridge-tile but with a steeper pitch. The longer C–Se bond lengths (2.2 Å) and smaller bond angles at C–Se–C (88°), as compared to C–CH2–C (∼1.5 Å, ∼106°), lead to an interplanar angle between the two dipyrrinones of only 72°, which is considerably less than that of bilirubin (∼100°) and close to that (74°) of its 10-thia-rubin analog. Despite the conformational distortion

  对称C（10）-selena胆红素类似物，8,12 -双（2-羧乙基）-7,13 -二甲基- 2,3,17,18四乙基-10- selenabiladiene- 交流 -1,19（21 ħ ，24 ħ ） -二酮合成自8-（2-羧基乙基）-2,3-二乙基-7-甲基- （10 ħ ）-dipyrrin -1-酮在一个步骤中通过与diselenyl二氯化物反应。selena-rubin表现出 UV - vis 和 NMR 其光谱性质类似于母体中胆红素，并且类似于胆红素和中胆红素，它采用分子内氢键键合的构型，形状像山脊状但间距更陡。与C–CH 2 –C（〜1.5Å，〜106°）相比，C–Se键长（2.2Å）和C–Se–C（88°）处较小的键角导致夹角在两个二吡啶酮之间的夹角仅为72°，大大低于胆红素的含量（约100°）和接近其10硫代-红蛋白类似物的值（74°）。尽管存在构象变形，硒对氧化的敏感