2,2',4,4'-tetramethyl-3,3'-dipyrromethane-5,5'-dicarboxylic acid | 68500-71-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯
• 英文名称: 2,2',4,4'-tetramethyl-3,3'-dipyrromethane-5,5'-dicarboxylic acid
• 英文别名: 5,5'-biscarboxy-2,2',4,4'-tetramethyl-3,3'-dipyrrolyl-methane；2,2',4,4'-tetramethyl-5,5'-biscarboxy-3,3'-dipyrromethane；bis(5-carboxyl-2,4-dimethyl-pyrrole-3-yl)-methane；1,1-bis(5-carboxy-2,4-dimethylpyrrole-3-yl)methane；4,4'-Methylenebis(3,5-dimethyl-1H-pyrrole-2-carboxylic acid)；4-[(5-carboxy-2,4-dimethyl-1H-pyrrol-3-yl)methyl]-3,5-dimethyl-1H-pyrrole-2-carboxylic acid
• CAS: 68500-71-0
• 化学式: C₁₅H₁₈N₂O₄
• 分子量: 290.319
• InChiKey: KMPWPYDEUUIGQX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  21
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  106
• 氢给体数：
  4
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2,2',4,4'-tetramethyl-3,3'-dipyrromethane-5,5'-dicarboxylic acid 在 氢溴酸 作用下， 以 甲醇 、 溶剂黄146 、 三氟乙酸 为溶剂， 反应 3.0h， 生成 bis(2,4,9-trimethyl-7,8-diethyldipyrrin-3-yl)methane dihydrobromide
  参考文献：
  名称：

  SYNTHESIS OF NOVEL TETRAPYRROLES AND THEIR ZINC COMPLEXES

  摘要：

  DOI：

  10.1080/00304940109356577
• 作为产物：
  描述：

  3,5-二甲基-1H-吡咯-2-甲酸苄酯 在 palladium on activated charcoal 盐酸 、 氢气 、 三乙胺 作用下， 以 四氢呋喃 、 甲醇 、 水 为溶剂， 20.0 ℃ 、101.33 kPa 条件下， 反应 28.0h， 生成 2,2',4,4'-tetramethyl-3,3'-dipyrromethane-5,5'-dicarboxylic acid
  参考文献：
  名称：

  Double-Helical Dinuclear Bis(dipyrromethene) Complexes Formed by Self-Assembly

  摘要：

  Bis(dipyrromethene) ligands linked by an alkyl spacer between beta and beta' positions are shown to give helical dimers or monomers, dependent upon the length of the alkyl linker, upon complexation. Ligands consisting of methylene, ethylene, and propylene linkers -(CH2)(n)- (n = 1, 2, and 3) give helical dimers, while longer linking chains (n = 4, 5, or 6) give monomers or mixtures of dimers and monomers. X-ray crystal structures of the dimeric zinc complexes (n = 1, 2, and 3) reveal that the angles between dipyrromethene planes and the extent of helicity in the complexes differ as the length of the linker varies. The extent of helicity was assessed and found to be dependent upon the length and, specifically, the conformational preferences of the alkyl spacer unit. The presence of an ethylene linker gave complexes of greatest helicity. The use of a methylene spacer gave less helical structures upon complexation, while propylene spacers gave only slightly helical complexes. Our studies identify the crucial importance that the conformational preferences of the beta-beta' alkyl spacer group plays in the coordination algorithm of self-assembly to form dipyrromethene based complexes.

  DOI：

  10.1021/jo000886p

文献信息

• A novel biliverdin with an inverted pyrrole subunit
  作者：Ravindra K. Pandey、Sam H. Leung、Timothy P. Forsyth、Kevin M. Smith

  DOI：10.1016/0040-4039(94)88409-9

  日期：1994.11

  The synthesis and spectroscopic properties of a novel biliverdin 4 with one inverted pyrrole ring are described; the dipyrromethane 8 and a,c-biladiene 6 were the key intermediates in the synthesis of 4.

  描述了具有一个倒置的吡咯环的新型biliverdin 4的合成和光谱性质。二吡咯甲烷8和a，c-胆二烯6是4合成的关键中间体。
• Synthesis and self-assembly of a novel tetrapyrrole containing dipyrrin units linked at the 3,3′-positions
  作者：Yi Zhang、Zheming Wang、Chunhua Yan、Genpei Li、Jinshi Ma

  DOI：10.1016/s0040-4039(00)01305-8

  日期：2000.9

  A novel ligand comprising two dipyrrin units linked by a CH2 spacer at the 3-position has been synthesized and used to prepare a double-stranded helical assembly. Its structure was confirmed by X-ray analysis. A new approach to 3,3'-linked dipyrromethanes with CH2 as the spacer is also reported. (C) 2000 Elsevier Science Ltd. All rights reserved.
• Double-Helical Dinuclear Bis(dipyrromethene) Complexes Formed by Self-Assembly
  作者：Alison Thompson、David Dolphin

  DOI：10.1021/jo000886p

  日期：2000.11.1

  Bis(dipyrromethene) ligands linked by an alkyl spacer between beta and beta' positions are shown to give helical dimers or monomers, dependent upon the length of the alkyl linker, upon complexation. Ligands consisting of methylene, ethylene, and propylene linkers -(CH2)(n)- (n = 1, 2, and 3) give helical dimers, while longer linking chains (n = 4, 5, or 6) give monomers or mixtures of dimers and monomers. X-ray crystal structures of the dimeric zinc complexes (n = 1, 2, and 3) reveal that the angles between dipyrromethene planes and the extent of helicity in the complexes differ as the length of the linker varies. The extent of helicity was assessed and found to be dependent upon the length and, specifically, the conformational preferences of the alkyl spacer unit. The presence of an ethylene linker gave complexes of greatest helicity. The use of a methylene spacer gave less helical structures upon complexation, while propylene spacers gave only slightly helical complexes. Our studies identify the crucial importance that the conformational preferences of the beta-beta' alkyl spacer group plays in the coordination algorithm of self-assembly to form dipyrromethene based complexes.
• A highly efficient preparation of N-confused cyclodecapyrroles
  作者：Qingqi Chen、David Dolphin

  DOI：10.1016/s0040-4039(01)00444-0

  日期：2001.5

  Cyclodecapyrroles, potential novel host systems, were synthesized in 78-88% yields by condensation of tripyrrane dialdehyde with bis(5-carboxyl-2,4-dimethyl-pyrrole-3-yl)-methane, ethane, and -propane in the presence of HBr and TFA. (C) 2001 Elsevier Science Ltd. All rights reserved.
• SYNTHESIS OF NOVEL TETRAPYRROLES AND THEIR ZINC COMPLEXES
  作者：Yi Zhang、Jin Shi Ma

  DOI：10.1080/00304940109356577

  日期：2001.2