Benzoic acid (S)-4-ethyl-2-oxo-chroman-5-yl ester | 155779-38-7

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 3,4-二氢香豆素
• 英文名称: Benzoic acid (S)-4-ethyl-2-oxo-chroman-5-yl ester
• 英文别名: [(4S)-4-ethyl-2-oxo-3,4-dihydrochromen-5-yl] benzoate
• CAS: 155779-38-7
• 化学式: C₁₈H₁₆O₄
• 分子量: 296.323
• InChiKey: AQWWOZDICHHZEP-LBPRGKRZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  22
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  52.6
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  Benzoic acid (S)-4-ethyl-2-oxo-chroman-5-yl ester 在 sodium hydroxide 作用下， 以 1,4-二氧六环 为溶剂， 反应 6.5h， 生成 (+)-3-(S)-(2,6-dimethoxyphenyl)pentanoic acid
  参考文献：
  名称：

  Preparation of chiral indanones and dihydrocoumarins; application to synthesis of (+)-3-(2,6-dimethoxyphenyl) pentanoic acid

  摘要：

  Chiral beta-aryl carboxylic acids, prepared by Michael addition of organocuprates to chiral unsaturated imides, are transformed into chiral 3-alkyl-4-benzoyloxyindan-1-ones via two intramolecular acylations, with intermediate formation of chiral 3-alkylindanones and corresponding dihydrocoumarins. The 3-(S)-ethyl-4-benzoyloxyindanone is transformed into(+)-3-(S)-(2,6-dimethoxyphenyl)pentanoic acid.

  DOI：

  10.1016/s0957-4166(00)80481-4
• 作为产物：
  描述：

  (S)-4-ethylchroman-2-one 在 氢氧化钾 、 三氯化铝 、 氯化亚砜 、 对甲苯磺酸 、 间氯过氧苯甲酸 作用下， 以 1,4-二氧六环 、 二氯甲烷 、 水 为溶剂， 反应 32.0h， 生成 Benzoic acid (S)-4-ethyl-2-oxo-chroman-5-yl ester
  参考文献：
  名称：

  Preparation of chiral indanones and dihydrocoumarins; application to synthesis of (+)-3-(2,6-dimethoxyphenyl) pentanoic acid

  摘要：

  Chiral beta-aryl carboxylic acids, prepared by Michael addition of organocuprates to chiral unsaturated imides, are transformed into chiral 3-alkyl-4-benzoyloxyindan-1-ones via two intramolecular acylations, with intermediate formation of chiral 3-alkylindanones and corresponding dihydrocoumarins. The 3-(S)-ethyl-4-benzoyloxyindanone is transformed into(+)-3-(S)-(2,6-dimethoxyphenyl)pentanoic acid.

  DOI：

  10.1016/s0957-4166(00)80481-4

文献信息

• Preparation of chiral indanones and dihydrocoumarins; application to synthesis of (+)-3-(2,6-dimethoxyphenyl) pentanoic acid
  作者：Elie Stephan、Richard Rocher、Jeaninc Aubouet、Guy Pourcelot、Pierre Cresson

  DOI：10.1016/s0957-4166(00)80481-4

  日期：1994.1

  Chiral beta-aryl carboxylic acids, prepared by Michael addition of organocuprates to chiral unsaturated imides, are transformed into chiral 3-alkyl-4-benzoyloxyindan-1-ones via two intramolecular acylations, with intermediate formation of chiral 3-alkylindanones and corresponding dihydrocoumarins. The 3-(S)-ethyl-4-benzoyloxyindanone is transformed into(+)-3-(S)-(2,6-dimethoxyphenyl)pentanoic acid.