5,5'-diformyl-4,4'-dimethyl-3,3'-bis-(methoxycarbonylethyl)-2,2'-dipyrryl ketone | 26019-74-9

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 5,5'-diformyl-4,4'-dimethyl-3,3'-bis-(methoxycarbonylethyl)-2,2'-dipyrryl ketone
• 英文别名: 5,5'-diformyl-3,3'-bis(2-methoxycarbonylethyl)-4,4'-dimethylpyrroketone；3,3'-(5,5'-diformyl-4,4'-dimethyl-2,2'-carbonyl-di-pyrrol-3-yl)-bis-propionic acid dimethyl ester；Bis-(5-formyl-3,2'-methoxycarbonylethyl-4-methyl-2-pyrryl)-keton；methyl 3-[5-formyl-2-[5-formyl-3-(3-methoxy-3-oxopropyl)-4-methyl-1H-pyrrole-2-carbonyl]-4-methyl-1H-pyrrol-3-yl]propanoate
• CAS: 26019-74-9
• 化学式: C₂₁H₂₄N₂O₇
• 分子量: 416.431
• InChiKey: MABRRBIHJQIVQE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  30
• 可旋转键数：
  12
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  135
• 氢给体数：
  2
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  5,5'-diformyl-4,4'-dimethyl-3,3'-bis-(methoxycarbonylethyl)-2,2'-dipyrryl ketone 在 氯化亚砜 、 三氟乙酸 作用下， 以 吡啶 、 甲醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 2.0h， 生成 3,3'-(3,7,12,17-tetramethyl-1,19-dioxo-8,13-divinyl-1,19,22,24-tetrahydro-21H-biline-2,18-diyl)-bis-propionic acid dimethyl ester
  参考文献：
  名称：

  γ-oxyprotoporphyrin IX的合成和pterobiline（胆绿素IX γ）

  摘要：

  的γ -内消旋-羟基衍生物protopor-卟啉IX的已经由双（formylpyrroly）酮和dispyrrolylmethane的缩合合成; 铁络合物后行氧化开环，得到胆绿素IX γ（ptrobiline），蓝-绿色颜料蝴蝶，从而提供了其生物合成的模型。。

  DOI：

  10.1039/c39810000763
• 作为产物：
  描述：

  3-{5-Formyl-2-[5-formyl-3-(2-methoxycarbonyl-ethyl)-4-methyl-1H-pyrrol-2-ylmethyl]-4-methyl-1H-pyrrol-3-yl}-propionic acid methyl ester 在 磺酰氯 作用下， 生成 5,5'-diformyl-4,4'-dimethyl-3,3'-bis-(methoxycarbonylethyl)-2,2'-dipyrryl ketone
  参考文献：
  名称：

  γ-oxyprotoporphyrin IX的合成和pterobiline（胆绿素IX γ）

  摘要：

  的γ -内消旋-羟基衍生物protopor-卟啉IX的已经由双（formylpyrroly）酮和dispyrrolylmethane的缩合合成; 铁络合物后行氧化开环，得到胆绿素IX γ（ptrobiline），蓝-绿色颜料蝴蝶，从而提供了其生物合成的模型。。

  DOI：

  10.1039/c39810000763

文献信息

• Synthesis of γ-oxyprotoporphyrin IX and pterobiline (biliverdin IX_γ)
  作者：Anthony H. Jackson、Rhiannydd M. Jenkins、D. Michael Jones、Stephen A. Matlin

  DOI：10.1039/c39810000763

  日期：——

  The γ-meso-hydroxy-derivative of protopor-phyrin IX has been synthesised by condensation of a bis(formylpyrroly) ketone and a dispyrrolylmethane; the iron complex underwent oxidative ring-opening to give biliverdin IXγ(ptrobiline), the blue -green butterfly pigment, thus providing a modle for its biosynthesis.

  的γ -内消旋-羟基衍生物protopor-卟啉IX的已经由双（formylpyrroly）酮和dispyrrolylmethane的缩合合成; 铁络合物后行氧化开环，得到胆绿素IX γ（ptrobiline），蓝-绿色颜料蝴蝶，从而提供了其生物合成的模型。。
• Clezy,P.S.; Diakiw,V., Australian Journal of Chemistry, 1971, vol. 24, p. 2665 - 2677
  作者：Clezy,P.S.、Diakiw,V.

  DOI：——

  日期：——
• Synthesis of a 10-Oxo-Bilirubin:  Effects of the Oxo Group on Conformation, Transhepatic Transport, and Glucuronidation
  作者：Qingqi Chen、Michael T. Huggins、David A. Lightner、Wilma Norona、Antony F. McDonagh

  DOI：10.1021/ja991814m

  日期：1999.10.1

  Bilirubin, the yellow pigment of jaundice, is a linear tetrapyrrole with a methylene group at its center, C(10), a position of crucial importance to its conformation and metabolism. The presence of the central methylene group allows the bilirubin to fold into an intramolecularly hydrogen-bonded conformation. This paper describes the first synthesis of a bilirubin analogue with an oxo group at C(10). The change from CH2 to C=O, from sp(3) to sp(2), is designed to stress the molecule at its hinge and relax its conformation. Such compounds have been suggested as potential oxidative metabolites of bilirubin in vivo. 10-Oxo-mesobilirubin-XIII alpha (1) is a red crystalline solid, unlike its parent, mesobilirubin-XIII alpha, which is a bright yellow solid. It is surprisingly polar, relative to the parent, yet it does not exhibit a significantly larger bicarbonate/chloroform partition coefficient. Like the parent, 1 appears to adopt an intramolecularly hydrogen-bonded ridge-tile-like conformation. In normal rats, 1 is metabolized to acylglucuronides, which are secreted into bile, but a portion of the administered dose is secreted into bile intact. In mutant rats (Gunn rats) lacking bilirubin glucuronyl transferase, 1 was excreted efficiently in bile in unchanged form, unlike the parent with a methylene group at C(10). Thus, introduction of the oxygen function at C(10) has little effect on hepatic uptake but a dramatic effect on canalicular secretion into bile.
• Synthesis of biliverdin IXγ (pterobilin)
  作者：Anthony H. Jackson、Rhianydd M. Jenkins、D.Michael Jones、Stephen A. Matlin

  DOI：10.1016/s0040-4020(01)88698-1

  日期：1983.1