bis(5-carboxyl-2,4-dimethyl-pyrrole-3-yl)-ethane | 68500-72-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯
• 英文名称: bis(5-carboxyl-2,4-dimethyl-pyrrole-3-yl)-ethane
• 英文别名: 1,2-bis(5-carboxy-2,4-dimethylpyrrole-3-yl)ethane；4-[2-(5-carboxy-2,4-dimethyl-1H-pyrrol-3-yl)ethyl]-3,5-dimethyl-1H-pyrrole-2-carboxylic acid
• CAS: 68500-72-1
• 化学式: C₁₆H₂₀N₂O₄
• 分子量: 304.346
• InChiKey: ICTRLPVYOJYRDE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  22
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.38
• 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：

  bis(5-carboxyl-2,4-dimethyl-pyrrole-3-yl)-ethane 、 4,4'-diethyl-3,3'-dimethyl-5,5'-methanediyl-bis-pyrrole-2-carbaldehyde 在 氢溴酸 、 溶剂黄146 、 三氟乙酸 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 以90%的产率得到
  参考文献：
  名称：

  Cyclooctapyrroles, novel macrocycles containing biladiene-a,c units

  摘要：

  Cyclooctapyrroles, novel macrocycles containing two biladiene-a,c units, were synthesized in high yield from the condensation of 3,3'-dipyrromethanes with 5,5'-diformyl-2,2'-dipyrromethane under acidic conditions. These macrocycles form dinuclear complexes with zinc(H). (C) 2003 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(02)01592-2
• 作为产物：
  描述：

  3,5-二甲基-1H-吡咯-2-甲酸乙酯 在 palladium on activated charcoal sodium tetrahydroborate 、 三氟化硼乙醚 、 氢气 、 四氯化锡 、 三乙胺 作用下， 以 四氢呋喃 、 二氯甲烷 、 乙酸乙酯 、 苯甲醇 为溶剂， 209.0 ℃ 、101.33 kPa 条件下， 反应 15.25h， 生成 bis(5-carboxyl-2,4-dimethyl-pyrrole-3-yl)-ethane
  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 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.
• 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.
• Cyclooctapyrroles, novel macrocycles containing biladiene-a,c units
  作者：Qingqi Chen、David Dolphin

  DOI：10.1016/s0040-4020(02)01592-2

  日期：2003.2

  Cyclooctapyrroles, novel macrocycles containing two biladiene-a,c units, were synthesized in high yield from the condensation of 3,3'-dipyrromethanes with 5,5'-diformyl-2,2'-dipyrromethane under acidic conditions. These macrocycles form dinuclear complexes with zinc(H). (C) 2003 Elsevier Science Ltd. All rights reserved.