4-bis(2-hydroxyethyl)-6,7-bis[2-(methoxycarbonyl)ethyl]-1,3,5,8-tetramethylporphyrin | 33070-12-1

• 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: 4-bis(2-hydroxyethyl)-6,7-bis[2-(methoxycarbonyl)ethyl]-1,3,5,8-tetramethylporphyrin
• 英文别名: 3,3'-[7,12-bis-(2-hydroxy-ethyl)-3,8,13,17-tetramethyl-21H,23H-porphine-2,18-diyl]-bis-propionic acid dimethyl ester
• CAS: 33070-12-1
• 化学式: C₃₆H₄₂N₄O₆
• 分子量: 626.753
• InChiKey: FZDPWTOGYDRWFC-SHWYJLMRSA-N

物化性质

• 熔点：
  222-226 °C
• 沸点：
  1081.7±65.0 °C(Predicted)
• 密度：
  1.247±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.77
• 重原子数：
  46.0
• 可旋转键数：
  10.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.39
• 拓扑面积：
  150.42
• 氢给体数：
  4.0
• 氢受体数：
  8.0

反应信息

• 作为反应物：
  描述：

  4-bis(2-hydroxyethyl)-6,7-bis[2-(methoxycarbonyl)ethyl]-1,3,5,8-tetramethylporphyrin 在 sodium sulfate 、 silver carbonate 作用下， 以 二氯甲烷 为溶剂， 生成 3-{(1Z,4Z,9Z,15Z)-18-(2-Carboxy-ethyl)-3,8,13,17-tetramethyl-7,12-bis-[2-((3R,4S,5S,6R)-3,4,5-trihydroxy-6-hydroxymethyl-tetrahydro-pyran-2-yloxy)-ethyl]-porphyrin-2-yl}-propionic acid
  参考文献：
  名称：

  Brunner, Henri; Maiterth, Friedrich; Treittinger, Barbara, Chemische Berichte, 1994, vol. 127, # 11, p. 2141 - 2150

  摘要：

  DOI：
• 作为产物：
  描述：

  3,3'-(3,7,12,17-tetramethyl-8,13-divinyl-21H,23H-porphine-2,18-diyl)-bis-propionic acid dimethyl ester 生成 4-bis(2-hydroxyethyl)-6,7-bis[2-(methoxycarbonyl)ethyl]-1,3,5,8-tetramethylporphyrin
  参考文献：
  名称：

  Vinyl group protection in porphyrins and chlorins: Organoselenium derivatives

  摘要：

  The o-nitrophenylselenoethyl functionality is a useful protected vinyl group in porphyrins and chlorins, and its use is demonstrated in the Vilsmeier formylation reaction which has been shown to adversely affect unmodified vinyl groups in tetrapyrrole systems. The X-ray crystal structure for 3-(2-o-nitrophenylselenoethyl)-3-devinylchlorin-e(6) trimethyl ester 14 is reported. (C) 1997, Elsevier Science Ltd.

  DOI：

  10.1016/s0040-4039(97)00002-6

文献信息

• Synthesis and biological evaluation of thioglycosylated porphyrins for an application in photodynamic therapy
  作者：I Sylvain、R Zerrouki、R Granet、Y.M Huang、J.-F Lagorce、M Guilloton、J.-C Blais、P Krausz

  DOI：10.1016/s0968-0896(01)00255-3

  日期：2002.1

  The aim of this work is the synthesis of a new family of glycosylated porphyrins in which the sugar moieties are linked to the tetrapyrrole ring by a thioglycosidic bond. Two series have been designed. The first one corresponds to meso-aryl porphyrin derivatives. The second one has been obtained from protoporphyrin IX derivatization. Aryl-porphyrins were prepared from tristolyl o- and p-hydroxyporphyrins followed by bromoallylation and thioglycosylation with peracetylated S-glucose, mannose and galactose and deprotection. The other series has been synthesized from protoporphyrin IX dimethylester with a regioselective glycosylation of terminal alkenyl carbon. The UV-visible, NMR and MALDI mass spectra are presented. Photocytotoxicities of the synthesized compounds against K562 chronic leukaemia cell line has been evaluated. (C) 2001 Elsevier Science Ltd. All rights reserved.
• Total syntheses of 8-formyl-8-demethylprotoporphyrin IX, 8-(hydroxymethyl)-8-demethylprotoporphyrin IX, and 8-fluoromethyl analogs of protoporphyrin IX
  作者：Kevin M. Snow、Kevin M. Smith

  DOI：10.1021/jo00275a009

  日期：1989.7
• Fuelling, Gerd; Schroeder, Doris; Franck, Burchard, Angewandte Chemie, 1989, vol. 101, # 11, p. 1550 - 1552
  作者：Fuelling, Gerd、Schroeder, Doris、Franck, Burchard

  DOI：——

  日期：——
• Improved Methods for the Synthesis of Porphyrin Alcohols and Aldehydes from Protoporphyrin IX Dimethyl Ester and Their Further Modification
  作者：Stephen B. Kahl、John J. Schaeck、Myoung-Seo Koo

  DOI：10.1021/jo961381v

  日期：1997.3.1