八乙基卟啉原 | 24477-51-8

• 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
• 中文名称: 八乙基卟啉原
• 英文名称: octaethyl porphyrinogen
• 英文别名: Octaethylporphyrinogen；2,3,7,8,12,13,17,18-octaethyl-porphyrinogen；2,3,7,8,12,13,17,18-Octaaethyl-porphyrinogen；Oktaaethylporphyrinogen；2,3,7,8,12,13,17,18-Octaethyl-5,10,15,20,21,22,23,24-octahydroporphyrin
• CAS: 24477-51-8
• 化学式: C₃₆H₅₂N₄
• 分子量: 540.836
• InChiKey: XAFDZPATADWMQG-UHFFFAOYSA-N

物化性质

• 沸点：
  658.8±50.0 °C(Predicted)
• 密度：
  1.064±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  9.5
• 重原子数：
  40
• 可旋转键数：
  8
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.56
• 拓扑面积：
  63.2
• 氢给体数：
  4
• 氢受体数：
  0

反应信息

• 作为反应物：
  描述：

  八乙基卟啉原 在 邻四氯苯醌 作用下， 以 二氯甲烷 为溶剂， 反应 24.0h， 生成 2,3,7,8,12,13,17,18-octaethyl-21,22-dihydroporphyrin
  参考文献：
  名称：

  Nonionic Superbase-Promoted Synthesis of Oxazoles and Pyrroles: Facile Synthesis of Porphyrins and .alpha.-C-Acyl Amino Acid Esters

  摘要：

  The reaction of acyl chlorides or acid anhydrides with isocyanoacetates in the presence of the superior strong nonionic base P(MeNCH(2)CH(2))(3)N (1) gave oxazoles in 98-99% yield. Treatment of the oxazoles with HCl-MeOH gave alpha-C-acyl amino acid esters in 81-82% yield. The reaction of beta-acetoxy-alpha-nitroalkanes or nitroalkenes with isocyanoacetates in the presence of 1 gave pyrroles in 100% yield. The conjugate acid of 1 can be treated with KO-t-Bu to regenerate 1. Treatment of the pyrroles with LiAlH4, followed by PTSA-CH2(OMe)(2) and oxidation gave porphyrins in 65-69% yield. LiCl, which functions both as a strong nucleophile in the S(N)2 demethylation of the 5,5'-bis(methoxycarbonyl)-3,3',4,4'-tetramethyldipyrromethane 22a and as a Lewis acid in the electrophilic substitution cyclization of paraformaldehyde at dipyrromethane, facilitates the combination of four reactions into a one-pot synthesis of octaethylporphyrin in 67% yield from 22a.

  DOI：

  10.1021/jo00104a041
• 作为产物：
  描述：

  2,3,7,8,12,13,17,18-octaethyl-21,22-dihydroporphyrin 在 platinum(IV) oxide 氢气 作用下， 以 溶剂黄146 为溶剂， 以73%的产率得到八乙基卟啉原
  参考文献：
  名称：

  Porphyrin synthesis by ring transplantation

  摘要：

  DOI：

  10.1016/s0040-4039(00)98256-x

文献信息

• Chemistry of pyrrocorphins: structure of nickel(II)ccccc-octaethyl-pyrrocorphinate in the solid state and in solution. Observation of the inversion barrier between enantiomorphically ruffled conformers
  作者：Rudolf Waditschatka、Christoph Kratky、Bernhard Jaun、Josef Heinzer、Albert Eschenmoser

  DOI：10.1039/c39850001604

  日期：——

  An inversion barrier between enantiomorphic saddle conformers of nickel(II)ccccc-octaethyl-pyrrocorphinate in solution is observed by 1H n.m.r. spectroscopy.

  通过1 H nmr光谱观察到溶液中镍（II）ccccc-八乙基-吡咯烷酸盐的对映体鞍形构象异构体之间的反型壁垒。
• Fischer; Baeumler, Justus Liebigs Annalen der Chemie, 1929, vol. 468, p. 61,74
  作者：Fischer、Baeumler

  DOI：——

  日期：——
• Nonionic Superbase-Promoted Synthesis of Oxazoles and Pyrroles: Facile Synthesis of Porphyrins and .alpha.-C-Acyl Amino Acid Esters
  作者：Jiansheng Tang、John G. Verkade

  DOI：10.1021/jo00104a041

  日期：1994.12

  The reaction of acyl chlorides or acid anhydrides with isocyanoacetates in the presence of the superior strong nonionic base P(MeNCH(2)CH(2))(3)N (1) gave oxazoles in 98-99% yield. Treatment of the oxazoles with HCl-MeOH gave alpha-C-acyl amino acid esters in 81-82% yield. The reaction of beta-acetoxy-alpha-nitroalkanes or nitroalkenes with isocyanoacetates in the presence of 1 gave pyrroles in 100% yield. The conjugate acid of 1 can be treated with KO-t-Bu to regenerate 1. Treatment of the pyrroles with LiAlH4, followed by PTSA-CH2(OMe)(2) and oxidation gave porphyrins in 65-69% yield. LiCl, which functions both as a strong nucleophile in the S(N)2 demethylation of the 5,5'-bis(methoxycarbonyl)-3,3',4,4'-tetramethyldipyrromethane 22a and as a Lewis acid in the electrophilic substitution cyclization of paraformaldehyde at dipyrromethane, facilitates the combination of four reactions into a one-pot synthesis of octaethylporphyrin in 67% yield from 22a.
• Lahiri, Goutam K.; Stolzenberg, Alan M., Angewandte Chemie, 1993, vol. 105, # 3, p. 440 - 443
  作者：Lahiri, Goutam K.、Stolzenberg, Alan M.

  DOI：——

  日期：——
• Johansen, Jon Eigill; Piermattie, Virginia; Angst, Christof, Angewandte Chemie, 1981, vol. 93, # 3, p. 273 - 275
  作者：Johansen, Jon Eigill、Piermattie, Virginia、Angst, Christof、Diener, Eva、Kratky, Christoph、Eschenmoser, Albert

  DOI：——

  日期：——