13,17-diethyl-3,7-bis(2-methoxycarbonylethyl)-2,8,12,18-tetramethylporphyrin | 992-32-5

• 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: 13,17-diethyl-3,7-bis(2-methoxycarbonylethyl)-2,8,12,18-tetramethylporphyrin
• 英文别名: mesoporphyrin III dimethyl ester；3,3'-(8,12-diethyl-3,7,13,17-tetramethyl-21H,23H-porphine-2,18-diyl)-bis-propionic acid dimethyl ester；1,4,5,8-Tetramethyl-2,3-diethyl-6,7-di(β-carbomethoxyethyl)porphin；Mesoporphyrindimethylester；Mesoporphyrin III；mesoporphyn II dimethyl ester；3,3'-(8,12-diethyl-3,7,13,17-tetramethyl-porphyrin-2,18-diyl)-di-propionic acid dimethyl ester；3,3'-(8,12-Diaethyl-3,7,13,17-tetramethyl-porphyrin-2,18-diyl)-di-propionsaeure-dimethylester；Mesoprophyrin III dimethylester; 1,4,5,8-Tetramethyl-2,3-diethyl-porphin-6,7-dipropionsaeure-dimethylester；2.3-Diaethyl-6.7-bis-<2-methoxycarbonyl-aethyl>-1.4.5.8-tetramethyl-porphin
• CAS: 992-32-5
• 化学式: C₃₆H₄₂N₄O₄
• 分子量: 594.754
• InChiKey: BUAGWBACWRGNNY-HODIFWHRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.82
• 重原子数：
  44.0
• 可旋转键数：
  8.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.39
• 拓扑面积：
  109.96
• 氢给体数：
  2.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  13,17-diethyl-3,7-bis(2-methoxycarbonylethyl)-2,8,12,18-tetramethylporphyrin 在 吡啶 、 四氧化锇 作用下， 生成
  参考文献：
  名称：

  在四吡咯亚基反应性和频哪醇频哪酮重排的替代效应：维克-dihydroxychlorins和VIC -dihydroxybacteriochlorins

  摘要：

  卟啉中吡咯亚基OsO 4氧化的区域专一性受到大环上吸电子基团的显着影响，氧化发生在与负电基团相反的象限中的亚基上。在卟啉和脱镁叶绿的后续频哪醇-频哪酮重排洄游性向VIC -二羟基系统同样是依赖于吸电子官能团的存在。

  DOI：

  10.1016/s0040-4039(00)74751-4
• 作为产物：
  描述：

  在 copper diacetate 氢溴酸 、 三氟乙酸 、 原甲酸三甲酯 作用下， 以 甲醇 、 溶剂黄146 、 N,N-二甲基甲酰胺 为溶剂， 反应 11.17h， 生成 13,17-diethyl-3,7-bis(2-methoxycarbonylethyl)-2,8,12,18-tetramethylporphyrin
  参考文献：
  名称：

  Smith, Kevin M.; Pandey, Ravindra K., Journal of the Chemical Society. Perkin transactions I, 1987, p. 1229 - 1236

  摘要：

  DOI：

文献信息

• Alternate Syntheses Of Pyrromethanes And Porphyrins Using Acid-Modified Montmorillonite K-10 Clay
  作者：Beverly A. Freeman、Kevin M. Smith

  DOI：10.1080/00397919908086174

  日期：1999.6

  Abstract A variety of porphyrins and pyrromethanes are prepared using Montmorillonite clay mixed with a variety of acids (p-TsOH, BF3 Et2O).The ease of use of the naturally occurring clay as a co-catalyst makes it an attractive reagent for use in synthesis.

  摘要 使用蒙脱石粘土与多种酸（p-TsOH、BF3 Et2O）混合可制备多种卟啉和吡咯甲烷。天然粘土作为助催化剂的易用性使其成为一种极具吸引力的合成试剂。 .
• Synthesis of a Series of Mono-<i>meso</i>-arylmesoporphyrins III of Biological Interest and Their Biliverdin Derivatives
  作者：Graciela Buldain、Fernando Niemevz、Ma. Vazquez

  DOI：10.1055/s-2008-1032203

  日期：2008.3

  MacDonald-type 2+2 condensation is described. In this method, the substituted 1,9-diformyldipyrromethane is treated with a dipyrromethane-1,9-dicarboxylic acid under acidic conditions. The 5-aryldipyrrolic unit was obtained by condensation of TERT-butyl, ethyl, or benzyl 4-ethyl-3-methyl-1 H-pyrrole-2-carboxylate with different aromatic aldehydes in the presence of 4-toluenesulfonic acid. In order to obtain

  描述了使用 MacDonald 型 2+2 缩合合成一系列单-MESO-芳基中卟啉 III。在该方法中，取代的 1,9-二甲酰基二吡咯甲烷在酸性条件下用二吡咯甲烷-1,9-二羧酸处理。5-芳基二吡咯单元是在 4-甲苯磺酸存在下通过 4-乙基-3-甲基-1 H-吡咯-2-羧酸叔丁酯、乙基或苄基酯与不同的芳香醛缩合获得的。为了获得相应的中胆绿素，对每种中卟啉进行化学氧化。每个 MESO-芳基中卟啉呈现两个异构的芳基胆绿素，因为卟啉 MESO-芳基桥没有被切割。
• Pinacol−Pinacolone Rearrangements in <i>vic-</i>Dihydroxychlorins and Bacteriochlorins:  Effect of Substituents at the Peripheral Positions
  作者：Ravindra K. Pandey、Meden Isaac、Craig J. Medforth、Mathias O. Senge、Thomas J. Dougherty、Kevin M. Smith

  DOI：10.1021/jo960720h

  日期：1997.3.1

  Upon reaction with osmium tetraoxide a series of porphyrins and chlorins were converted into the corresponding vic-dihydroxychlorins and bacteriochlorins. The presence of an electron-withdrawing substituent at a peripheral position on the porphyrins or chlorins deactivated that particular pyrrole unit toward oxidation, and also directed the oxidation regioselectively to the pyrrole ring opposite to the one bearing the electronegative group. The vic-dihydroxychlorins and bacteriochlorins were converted into the corresponding oxochlorins and dioxobacteriochlorins under pinacol-pinacolone reaction conditions. The migratory behavior of the various substituents were found to be quite complex, since distant conjugated peripheral substituents were able to affect the stability of the carbocation intermediates during the process; the ability to rearrange was affected not only by the intrinsic nature of the migratory group but also by steric and electronic factors operative elsewhere on the porphyrin and chlorin macrocycles. Preferential migration of the propionic ester over the methyl substituent in dioxobacteriochlorins obtained from 2,3,12,13-tetrahydroxycoproporphyrin II tetramethyl ester (IUPAC nomenclature) under pinacol-pinacolone conditions was confirmed by a single crystal X-ray study. The dioxobacteriochlorins obtained from mesoporphyrin III dimethyl ester and coproporphyrin II tetramethyl ester were converted into the corresponding dithioanalogues using Lawesson's reagent; this caused a red shift of 62 nm (compared with the dioxo compounds) affording long wavelength absorption at lambda(max) 746 nm.
• Lee, David A.; Smith, Kevin M., Journal of the Chemical Society. Perkin transactions I, 1997, # 8, p. 1215 - 1227
  作者：Lee, David A.、Smith, Kevin M.

  DOI：——

  日期：——