3-(2-carbethoxy-5-formyl-4-methyl-1H-3-pyrrolyl)propanoic acid | 634606-10-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯
• 英文名称: 3-(2-carbethoxy-5-formyl-4-methyl-1H-3-pyrrolyl)propanoic acid
• 英文别名: 3-(2-carboxyethyl)-5-formyl-4-methyl-1H-pyrrole-2-carboxylic acid
• CAS: 634606-10-3
• 化学式: C₁₀H₁₁NO₅
• 分子量: 225.201
• InChiKey: XARKVBKCSRRBAX-UHFFFAOYSA-N

物化性质

• 熔点：
  >150 °C (decomp)
• 沸点：
  496.6±45.0 °C(Predicted)
• 密度：
  1.479±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.5
• 重原子数：
  16
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  108
• 氢给体数：
  3
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  3-(2-carbethoxy-5-formyl-4-methyl-1H-3-pyrrolyl)propanoic acid 在 potassium acetate 、 sodium acetate 作用下， 反应 50.0h， 以71%的产率得到3-(5-formyl-4-methyl-1H-pyrrol-3-yl)propionic acid
  参考文献：
  名称：

  Plieninger, Hans; Preuss, Ingo, Liebigs Annalen der Chemie, 1983, # 4, p. 585 - 598

  摘要：

  DOI：
• 作为产物：
  描述：

  ethyl 5-formyl-3-(2-ethoxycarbonyl)ethyl-4-methyl-1H-pyrrole-2-carboxylate 在 lithium hydroxide 作用下， 以 四氢呋喃 、 水 为溶剂， 反应 4.0h， 以85%的产率得到3-(2-carbethoxy-5-formyl-4-methyl-1H-3-pyrrolyl)propanoic acid
  参考文献：
  名称：

  A New Class of Linear Tetrapyrroles:  Acetylenic 10,10a-Didehydro-10a-homobilirubins

  摘要：

  Novel bilirubin analogues with dipyrrinones conjoined to an acetylene rather than a methylene group were synthesized and examined spectroscopically. Despite the increased separation of the dipyrrinones forced by replacing a -CH2- by a -Cequivalent toC- unit, molecular dynamics calculations show that, like bilirubin, they may still engage in intramolecular hydrogen bonding to carboxylic acid groups when the propionic acid chains are slightly lengthened, e.g., butanoic acids. Unlike bilirubin, however, which is bent in the middle and has a ridge-tile shape, the acetylene orients the attached dipyrrinones along a linear path, and intramolecular hydrogen bonding preserves a twisted linear molecular shape. The extended planes of the dipyrrinones intersect along the -Cequivalent toC- axis at an angle of 136degrees for the conformation stabilized by intramolecular hydrogen bonding in the bis-butyric acid rubin (1b). With shorter acid chains (propionic), only one CO2H can engage an opposing dipyrrinone in intramolecular hydrogen bonding, and in this energy-minimum conformation of the linear pigment la, the intersection of the extended planes of the dipyrrinones has an angle of 171degrees. Spectroscopic evidence for such linearized and twisted structures was found in the pigments' NMR spectral data and their exciton UV-vis and induced circular dichroism spectra.

  DOI：

  10.1021/jo030252t

文献信息

• US20140275033A1
  申请人：——

  公开号：US20140275033A1

  公开（公告）日：2014-09-18
• US9187454B2
  申请人：——

  公开号：US9187454B2

  公开（公告）日：2015-11-17
• A New Class of Linear Tetrapyrroles:  Acetylenic 10,10a-Didehydro-10a-homobilirubins
  作者：Bin Tu、Brahmananda Ghosh、David A. Lightner

  DOI：10.1021/jo030252t

  日期：2003.11.1

  Novel bilirubin analogues with dipyrrinones conjoined to an acetylene rather than a methylene group were synthesized and examined spectroscopically. Despite the increased separation of the dipyrrinones forced by replacing a -CH2- by a -Cequivalent toC- unit, molecular dynamics calculations show that, like bilirubin, they may still engage in intramolecular hydrogen bonding to carboxylic acid groups when the propionic acid chains are slightly lengthened, e.g., butanoic acids. Unlike bilirubin, however, which is bent in the middle and has a ridge-tile shape, the acetylene orients the attached dipyrrinones along a linear path, and intramolecular hydrogen bonding preserves a twisted linear molecular shape. The extended planes of the dipyrrinones intersect along the -Cequivalent toC- axis at an angle of 136degrees for the conformation stabilized by intramolecular hydrogen bonding in the bis-butyric acid rubin (1b). With shorter acid chains (propionic), only one CO2H can engage an opposing dipyrrinone in intramolecular hydrogen bonding, and in this energy-minimum conformation of the linear pigment la, the intersection of the extended planes of the dipyrrinones has an angle of 171degrees. Spectroscopic evidence for such linearized and twisted structures was found in the pigments' NMR spectral data and their exciton UV-vis and induced circular dichroism spectra.
• Plieninger, Hans; Preuss, Ingo, Liebigs Annalen der Chemie, 1983, # 4, p. 585 - 598
  作者：Plieninger, Hans、Preuss, Ingo

  DOI：——

  日期：——