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：——
• Microwave-Assisted Piloty−Robinson Synthesis of 3,4-Disubstituted Pyrroles
  作者：Benjamin C. Milgram、Katrine Eskildsen、Steven M. Richter、W. Robert Scheidt、Karl A. Scheidt

  DOI：10.1021/jo070389+

  日期：2007.5.1

  [GRAPHICS]The synthesis of N-acyl 3,4-disubstituted pyrroles can be accomplished directly from hydrazine and an aldehyde via a Piloty-Robinson pyrrole synthesis. The use of microwave radiation for the cyclization and pyrrole formation greatly reduces the time necessary for this process and facilitates moderate to good yields from hydrazine for the corresponding 3,4-disubstituted products (5-12). By simple hydrolysis, the free N-H pyrroles can be accessed after the Piloty-Robinson reaction and then used directly in the synthesis of octaethylporphyrin (H2OEP, 14) and octaethyltetraphenylporphyrin (H2OETPP, 15).
• 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：——