3,3'-dimethoxycarbonylethyl-4,4'-dimethyl-2,2'-dipyrromethane | 802-52-8

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: 3,3'-dimethoxycarbonylethyl-4,4'-dimethyl-2,2'-dipyrromethane
• 英文别名: methyl 3-[2-[[3-(3-methoxy-3-oxopropyl)-4-methyl-1H-pyrrol-2-yl]methyl]-4-methyl-1H-pyrrol-3-yl]propanoate
• CAS: 802-52-8
• 化学式: C₁₉H₂₆N₂O₄
• 分子量: 346.426
• InChiKey: LIKVLOHIWRJBEI-UHFFFAOYSA-N

物化性质

• 熔点：
  56-58 °C
• 沸点：
  481.2±40.0 °C(Predicted)
• 密度：
  1.167±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  25
• 可旋转键数：
  10
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.47
• 拓扑面积：
  84.2
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  3,3'-dimethoxycarbonylethyl-4,4'-dimethyl-2,2'-dipyrromethane 在 1,8-二氮杂双环[5.4.0]十一碳-7-烯 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 1.0h， 生成 Protoporphyrin-III-dimethylester
  参考文献：
  名称：

  从常见的起始吡咯合成原卟啉III和XIII的新途径

  摘要：

  基于单一的原料，即2,4-二甲基-3-（2-氯乙基）碳乙氧基吡咯（4）和3，开发了一种新的原卟啉III（2'）和XIII（3'）方法。3 ' -二（2-甲氧羰基乙基）-4,4- ' -dimethyldipyrromethane -5,5- ' -二羧酸（5），用于两个靶。采用胆二烯路线制备2'（五个步骤，总产率18％），同时使用两个吡咯并蒽的偶联来合成3'（四个步骤，总产率11％）。

  DOI：

  10.1016/s0040-4039(02)00466-5
• 作为产物：
  描述：

  5-acetoxymethyl-4-methyl-3-methoxycarbonylethyl-2-(t-butoxycarbonyl)-pyrrole 在 对甲苯磺酸 、 三氟乙酸 作用下， 以 水 、 溶剂黄146 为溶剂， 反应 7.0h， 生成 3,3'-dimethoxycarbonylethyl-4,4'-dimethyl-2,2'-dipyrromethane
  参考文献：
  名称：

  Synthesis of a 10-Oxo-Bilirubin:  Effects of the Oxo Group on Conformation, Transhepatic Transport, and Glucuronidation

  摘要：

  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.

  DOI：

  10.1021/ja991814m

文献信息

• BIS-MYOGLOBIN RECONSTITUTED WITH COVALENTLY BONDED SYMMETRIC HEMES
  作者：Akihiro Suzuki、Katsuya Okuda、Keiko Kawagoe、Hiroo Toi、Yasuhiro Aoyama、Hisanobu Ogoshi

  DOI：10.1246/cl.1985.1169

  日期：1985.8.5

  Two symmetric hemins were covalently bonded with polymethylene diamine. Reconstitution of bis-hemin with sperm whale apomyoglobin afforded bis-myoglobin(bis-Mb). Absorption spectra and paramagnetic 1H-NMR spectrum of bis-Mb were compared with monomeric myoglobin reconstituted with symmetric heme.

  两个对称的血红素与聚亚甲基二胺共价键合。用抹香鲸肌红蛋白重构双hemin，得到了双肌红蛋白（bis-Mb）。将双-Mb 的吸收光谱和顺磁 1H-NMR 光谱与用对称血红素重组的单体肌红蛋白进行了比较。
• Selective syntheses of unsymmetrical meso-arylporphyrins
  作者：Tadashi Ema、Yasuhisa Kuroda、Hisanobu Ogoshi

  DOI：10.1016/0040-4039(91)80031-z

  日期：——

  A selective synthetic route to unsymmetrical meso-arylporphyrins is described. New hybrid type of unsymmetrical porphyrin with C2-nu symmetry was prepared according to the new method.
• Mironov, A. F.; Nizhnik, A. N.; Kozhich, D. T., Journal of general chemistry of the USSR, 1981, vol. 51, # 3, p. 565 - 571
  作者：Mironov, A. F.、Nizhnik, A. N.、Kozhich, D. T.、Kozyrev, A. N.、Evstigneeva, R. P.

  DOI：——

  日期：——
• Studies in Chlorin Chemistry. 3. A Practical Synthesis of C,D-Ring Symmetric Chlorins of Potential Utility in Photodynamic Therapy
  作者：William G. O'Neal、William P. Roberts、Indranath Ghosh、Hui Wang、Peter A. Jacobi

  DOI：10.1021/jo060041z

  日期：2006.4.1

  C,D-ring symmetric chlorins 8 were prepared in 47-85% yield, on scales up to several hundred milligrams, by condensation of appropriately substituted bis-formyldihydrodipyrrins 6 and dipyrromethane biscarboxylic acids 7 in 5% TFA/CH2Cl2 (25 examples). Target chlorins were chosen to systematically probe the effect of lipophilic and hydrophilic substituents on tissue partitioning and cellular membrane penetration in photodynamic therapy (PDT).
• Synthesis and study of chlorin and porphyrin dimers with ether linkage
  作者：Alexander S Brandis、Andre N Kozyrev、Andrey F Mironov

  DOI：10.1016/s0040-4020(01)88238-7

  日期：1992.1

  Novel dimers of chlorophyll compounds (pheophorbide a, chlorin p6) and model porphyrin with ether linkage were synthesized and separated into components A and B (less and more polar). The ratio of these components was the same for all dimers and irrespective of reaction conditions. Method of dimerization through trifluoroacetoxyethylderivative gave higher yields.