ethyl 3-phenyl-4,5,6,7-tetrahydro-1H-indole-2-carboxylate | 89649-42-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯
• 英文名称: ethyl 3-phenyl-4,5,6,7-tetrahydro-1H-indole-2-carboxylate
• 英文别名: ethyl 3-phenyl-4,5,6,7-tetrahydroindole-2-carboxylate；1H-Indole-2-carboxylic acid, 4,5,6,7-tetrahydro-3-phenyl-, ethyl ester
• CAS: 89649-42-3
• 化学式: C₁₇H₁₉NO₂
• 分子量: 269.343
• InChiKey: CJRNRLZSZORSGP-UHFFFAOYSA-N

物化性质

• 沸点：
  493.7±45.0 °C(Predicted)
• 密度：
  1.149±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.1
• 重原子数：
  20
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.35
• 拓扑面积：
  42.1
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  ethyl 3-phenyl-4,5,6,7-tetrahydro-1H-indole-2-carboxylate 在 乙醇 、 sodium hydroxide 作用下， 以 四氢呋喃 为溶剂， 反应 48.0h， 生成 3-phenyl-4,5,6,7-tetrahydro-1H-indole-2-carboxylic acid
  参考文献：
  名称：

  [EN] INHIBITORS OF METALLO-BETA-LACTAMASES
  [FR] INHIBITEURS DE MÉTALLO-BÊTA-LACTAMASES

  摘要：

  本发明涉及式（I）的化合物，其作为细菌金属β-内酰胺酶的抑制剂。本发明还涉及制备这些化合物的方法，包括它们的药物组合物，以及它们在治疗细菌感染中的应用。

  公开号：

  WO2018215799A1
• 作为产物：
  描述：

  3-苯基-吲哚-2-羧酸乙酯 在 palladium on activated charcoal 氢气 作用下， 以 乙醇 为溶剂， 20.0 ℃ 、344.74 kPa 条件下， 反应 24.0h， 以58%的产率得到ethyl 3-phenyl-4,5,6,7-tetrahydro-1H-indole-2-carboxylate
  参考文献：
  名称：

  Collot, Valerie; Schmitt, Martine; Marwah, Padma, Heterocycles, 1999, vol. 51, # 12, p. 2823 - 2847

  摘要：

  DOI：

文献信息

• A new and practical synthesis of pyrroles
  作者：Béatrice Quiclet-Sire、Isabelle Thévenot、Samir Z. Zard

  DOI：10.1016/0040-4039(95)02001-2

  日期：1995.12

  Heating γ-nitroketoncs bearing an electron-withdrawing group such as an ester geminal to the nitro group with formamidinesulfinic acid and triethylamine in isopropanol produces pyrroles in good yield.

  在异丙醇中加热带有吸电子基团（例如与该硝基成双的酯的酯）的γ-硝基酮与甲am亚磺酸和三乙胺在异丙醇中加热，可以得到高产率的吡咯。
• 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, Michael P., Journal of the Chemical Society. Perkin transactions I, 1984, p. 111 - 118
  作者：Law, Kam Wah、Lai, Ting-Fong、Sammes, Michael P.、Katritzky, Alan R.、Mak, Thomas C.W.

  DOI：——

  日期：——
• Synthesis of 3-Phenylindoline-2-carboxamides as Semi-Rigid Phenylalanine Mimetics
  作者：Valérie Collot、Martine Schmitt、Ashok K Marwah、Bernadette Norberg、Jean-Jacques Bourguignon

  DOI：10.1016/s0040-4039(97)10214-3

  日期：1997.11

  Regioselective catalytic hydrogenation of N-acyl 3-phenylindole-2-carboxylates is the key step for the preparation of cis and trans indoline-2-carboxamides which can be considered as phenylalanine semi-rigid derivatives. (C) 1997 Published by Elsevier Science Ltd.
• 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：——