7-Hydroxy-3-phenyl-4,5,6,7-tetrahydro-1H-indole-2-carboxylic acid | 1026633-03-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯
• 英文名称: 7-Hydroxy-3-phenyl-4,5,6,7-tetrahydro-1H-indole-2-carboxylic acid
• CAS: 1026633-03-3
• 化学式: C₁₅H₁₅NO₃
• 分子量: 257.289
• InChiKey: KQGVHCVHDDWYAJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  19
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  73.3
• 氢给体数：
  3
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  7-Hydroxy-3-phenyl-4,5,6,7-tetrahydro-1H-indole-2-carboxylic acid 在 溶剂黄146 、 potassium hexacyanoferrate(III) 作用下， 反应 1.0h， 生成 2,7,12,17-tetraphenyl-3,5:8,10:13,15:18,20-tetrapropanoporphyrin
  参考文献：
  名称：

  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

  摘要：

  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.

  DOI：

  10.1021/jo00044a012
• 作为产物：
  描述：

  ethyl 7-acetoxy-3-phenyl-4,5,6,7-tetrahydro-1H-indole-2-carboxylate 在 氢氧化钾 作用下， 以 甲醇 为溶剂， 反应 1.0h， 生成 7-Hydroxy-3-phenyl-4,5,6,7-tetrahydro-1H-indole-2-carboxylic acid
  参考文献：
  名称：

  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

  摘要：

  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.

  DOI：

  10.1021/jo00044a012

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.