(+/-)-5-acetoxy-7-methyl-4-phenyl-3,4-dihydrocoumarin | 101723-81-3

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 新黄酮类化合物
• 英文名称: (+/-)-5-acetoxy-7-methyl-4-phenyl-3,4-dihydrocoumarin
• 英文别名: 5-acetoxy-7-methyl-4-phenyl-3,4-dihydrocoumarin；5-acetoxy-7-methyl-4-phenyl-chroman-2-one；5-Acetoxy-7-methyl-4-phenyl-chroman-2-on；(7-methyl-2-oxo-4-phenyl-3,4-dihydrochromen-5-yl) acetate
• CAS: 101723-81-3
• 化学式: C₁₈H₁₆O₄
• 分子量: 296.323
• InChiKey: ICKINLBBQDKSGO-UHFFFAOYSA-N

物化性质

• 熔点：
  163-164 °C
• 沸点：
  408.6±45.0 °C(Predicted)
• 密度：
  1.225±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.36
• 重原子数：
  22.0
• 可旋转键数：
  2.0
• 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：
  0.0
• 氢受体数：
  4.0

反应信息

• 作为产物：
  描述：

  肉桂酸 在 吡啶 、 盐酸 、 4-二甲氨基吡啶 作用下， 以 水 为溶剂， 反应 12.0h， 生成 (+/-)-5-acetoxy-7-methyl-4-phenyl-3,4-dihydrocoumarin
  参考文献：
  名称：

  Synthetic and novel biocatalytic resolution studies on (±)-5/6/7-acetoxy-4-aryl-3,4-dihydrocoumarins

  摘要：

  Eleven (+/-)-5/6/7-acetoxy-4-aryl-3,4-dihydrocoumarins have been synthesised in two steps starting from the coupling of cinnamic acid/substituted cinnamic acid with appropriate phenols, followed by acetylation in 50-83% overall yields. All hydroxy- and acetoxycoumarins were unambiguously identified on the basis of their spectral data. Candida antarctica lipase-catalysed deacetylation of these racemic acetoxydihydrocoumarins in dioxane occurred with moderate enantioselectivity. This is one of the rare examples of resolution using phenolic ester moiety as a remote handle for chiral recognition by a lipase. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0968-0896(02)00454-6

文献信息

• 280. The reaction between cinnamic acid and phenols in presence of hydrochloric acid. A new method for the preparation of 3 : 4-dihydro-4-phenylcoumarins
  作者：J. D. Simpson、Henry Stephen

  DOI：10.1039/jr9560001382

  日期：——