ethyl 3-phenylcyclooctapyrrole-2-carboxylate | 89649-44-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯
• 英文名称: ethyl 3-phenylcyclooctapyrrole-2-carboxylate
• 英文别名: ethyl 3-phenyl-4,5,6,7,8,9-hexahydro-1H-cycloocta[b]pyrrole-2-carboxylate
• CAS: 89649-44-5
• 化学式: C₁₉H₂₃NO₂
• 分子量: 297.397
• InChiKey: HQUXNTXPRISKCX-UHFFFAOYSA-N

物化性质

• 沸点：
  514.5±50.0 °C(Predicted)
• 密度：
  1.102±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.2
• 重原子数：
  22
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  42.1
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  1-[(1E)-1-环辛烯-1-基]吡咯烷 在 盐酸 作用下， 以 甲醇 为溶剂， 生成 ethyl 3-phenylcyclooctapyrrole-2-carboxylate
  参考文献：
  名称：

  Law, Kam Wah; Lai, Ting-Fong; Sammes, Michael P., Journal of the Chemical Society. Perkin transactions I, 1984, p. 111 - 118

  摘要：

  DOI：

文献信息

• Porphyrins with exocyclic rings. 1. Chemistry of 4,5,6,7-tetrahydro-1H-indoles: synthesis of acetoxy derivatives, dihydroindoles, and novel porphyrins with four exocyclic rings
  作者：Timothy D. Lash、Karla A. Bladel、Craig M. Shiner、Donna L. Zajeski、Rajiv P. Balasubramaniam

  DOI：10.1021/jo00044a012

  日期：1992.8

  A variety of 4,5,6,7-tetrahydro-1H-indoles (THI's) and 4-oxo-4,5,6,7-tetrahydro-1H-indoles (4-oxoTHIs) have been synthesized from cyclohexanone and 1,3-cyclohexanedione, respectively. The THI's reacted regioselectively with lead tetraacetate in acetic acid to give the 7-acetoxy derivatives. The isomeric 4-acetoxyTHI's were prepared by first reducing the corresponding 4-oxoTHI's with sodium borohydride and then reacting the resulting hydroxyTHI' s with acetic acid-pyridine. Both series of acetoxyTHI's underwent elimination of acetic acid when heated with pyridine-acetic anhydride to give dihydroindoles. The 7-acetoxyTHI's were hydrolyzed with potassium hydroxide in methanol-water and carefully neutralized with hydrochloric acid to give the corresponding hydroxyTHI carboxylic acids. Treatment with potassium ferricyanide in refluxing acetic acid gave good yields of tetrapropanoporphyrins when 3-methyl-, 3-ethyl-, or 3-n-propyl substituents were present. The 3-phenylTHI gave variable yields of the corresponding tetraphenylporphyrin. The 3-isopropylTHI gave only trace amounts of porphyrin under these conditions, and the 3-tert-butylTHI failed to give any porphyrin product. THI's with 6-methyl or 6,6-dimethyl substituents were prepared in two steps from 5-methyl-1,3-cyclohexanedione or dimedone, respectively. These compounds also reacted smoothly with lead tetraacetate to give the 7-acetoxy derivatives in high yield. Attempts to convert the 6,6-dimethylTHI's into symmetrical porphyrins were unsuccessful, although the 6-methylTHI gave a mixture of porphyrin stereoisomers in low yield. The influence of alkyl substituents and carbocyclic rings on the cyclotetramerization of THI's is discussed.
• LAW, KAM, WAH;LAI, TING-FONG;SAMMES, M. P.;KATRITZKY, A. R.;MAK, T. C. W., J. CHEM. SOC. PERKIN TRANS., 1984, N 1, 111-118
  作者：LAW, KAM, WAH、LAI, TING-FONG、SAMMES, M. P.、KATRITZKY, A. R.、MAK, T. C. W.

  DOI：——

  日期：——