cis-2-(1H-pyrrol-1-yl)-α-phenylcinnamic acid | 323185-55-3

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 二苯乙烯类
• 英文名称: cis-2-(1H-pyrrol-1-yl)-α-phenylcinnamic acid
• 英文别名: (Z)-2-phenyl-3-(2-pyrrol-1-ylphenyl)prop-2-enoic acid
• CAS: 323185-55-3
• 化学式: C₁₉H₁₅NO₂
• 分子量: 289.334
• InChiKey: GWOFQEYATAYEPS-VKAVYKQESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.1
• 重原子数：
  22.0
• 可旋转键数：
  4.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  42.23
• 氢给体数：
  1.0
• 氢受体数：
  2.0

反应信息

• 作为反应物：
  描述：

  cis-2-(1H-pyrrol-1-yl)-α-phenylcinnamic acid 在 palladium on activated charcoal 五氯化磷 、 氢气 作用下， 以 乙酸乙酯 、 1,2-二氯乙烷 为溶剂， 20.0 ℃ 、101.33 kPa 条件下， 反应 4.0h， 生成 (+/-)-5,6-dihydro-5-phenyl-4H-pyrrolo[1,2-a][1]benzoxazepin-4-one
  参考文献：
  名称：

  Polycondensed Heterocycles. Part 11: Preparation and Regioselective Reductions of 5-Phenyl-4H-pyrrolo[1,2-a][1]benzazepin-4-one

  摘要：

  The Wadsworth-Emmons olefination between 2-(1H-pyrrol-1-yl)benzaldehyde and methyl alpha-(diethylphosphonyl)phenyl acetate leads exclusively to the cis-isomer of methyl 2-(1H-pyrrol-1-yl)-alpha -phenylcinnamate, which, after transformation into the corresponding acid chloride, was easily cyclised to the title enone. This latter was regioselectively reduced to the corresponding saturated ketone or unsaturated alcohol, under different experimental conditions. An improved preparation of starting 2-(1H-pyrrol-1-yl)benzaldehyde is also reported. (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(00)00900-5
• 作为产物：
  描述：

  methyl 2-(diethoxyphosphoryl)-2-phenylacetate 在 lithium hydroxide 、 sodium hydride 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 反应 17.17h， 生成 cis-2-(1H-pyrrol-1-yl)-α-phenylcinnamic acid
  参考文献：
  名称：

  Polycondensed Heterocycles. Part 11: Preparation and Regioselective Reductions of 5-Phenyl-4H-pyrrolo[1,2-a][1]benzazepin-4-one

  摘要：

  The Wadsworth-Emmons olefination between 2-(1H-pyrrol-1-yl)benzaldehyde and methyl alpha-(diethylphosphonyl)phenyl acetate leads exclusively to the cis-isomer of methyl 2-(1H-pyrrol-1-yl)-alpha -phenylcinnamate, which, after transformation into the corresponding acid chloride, was easily cyclised to the title enone. This latter was regioselectively reduced to the corresponding saturated ketone or unsaturated alcohol, under different experimental conditions. An improved preparation of starting 2-(1H-pyrrol-1-yl)benzaldehyde is also reported. (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(00)00900-5

文献信息

• Polycondensed Heterocycles. Part 11: Preparation and Regioselective Reductions of 5-Phenyl-4H-pyrrolo[1,2-a][1]benzazepin-4-one
  作者：Antonio Garofalo、Gaetano Ragno、Giuseppe Campiani、Antonella Brizzi、Vito Nacci

  DOI：10.1016/s0040-4020(00)00900-5

  日期：2000.11

  The Wadsworth-Emmons olefination between 2-(1H-pyrrol-1-yl)benzaldehyde and methyl alpha-(diethylphosphonyl)phenyl acetate leads exclusively to the cis-isomer of methyl 2-(1H-pyrrol-1-yl)-alpha -phenylcinnamate, which, after transformation into the corresponding acid chloride, was easily cyclised to the title enone. This latter was regioselectively reduced to the corresponding saturated ketone or unsaturated alcohol, under different experimental conditions. An improved preparation of starting 2-(1H-pyrrol-1-yl)benzaldehyde is also reported. (C) 2000 Elsevier Science Ltd. All rights reserved.