(+/-)-7-acetoxy-4-phenyl-3,4-dihydrocoumarin | 31231-28-4

• 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: (+/-)-7-acetoxy-4-phenyl-3,4-dihydrocoumarin
• 英文别名: (2-Oxo-4-phenyl-3,4-dihydrochromen-7-yl) acetate
• CAS: 31231-28-4
• 化学式: C₁₇H₁₄O₄
• 分子量: 282.296
• InChiKey: MAIXMJMJFNLBCA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  21
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  52.6
• 氢给体数：
  0
• 氢受体数：
  4

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 (+/-)-7-acetoxy-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

• Clayton et al., Journal of the Chemical Society, 1953, p. 581,584
  作者：Clayton et al.

  DOI：——

  日期：——
• Absence of toxicity in Swiss mice following treatment with 7-acetoxy-4-aryl-3,4-dihydrocoumarin: Acute and repeated-dose toxicity study
  作者：Gláucio Barros Saldanha、Glaucia Barros Saldanha、Marina Rebeca Soares Carneiro de Sousa、George Laylson da Silva Oliveira、Ana Paula dos Santos C.L. da Silva、Jorge M. David、Juceni Pereira David

  DOI：10.1016/j.yrtph.2018.01.003

  日期：2018.4

  Neoflavonoids, which are classified as 4-arylcoumarin (neoflavone), 3,4-dihydro-4-arylcoumarin and neoflavene, have been the subject of a number of studies with respect to their therapeutic potential and, despite promising in vitro, ex vivo and in vivo pharmacological activities, there is a lack of studies demonstrating their toxicological properties. Therefore, this study aims to evaluate the acute (14 days) and repeated-dose (28 days) toxicity of synthetic neoflavonoid 7-acetoxy-4-aryl-3,4-dihydrocoumarin in Swiss mice through parameters related to changes in body weight, food and water intake, hematological and biochemical parameters. Toxicity studies using acute doses (300 and 2000 mg/kg) and repeated doses (250, 500 and 1000 mg/kg) orally were carried out as per Organization for Economic Co-operation and Development (OECD) guidelines 423 and 407, respectively. Based on the results of this study, treatment with 7-acetoxy-4-aryl-3,4-dihydrocoumarin was found to not cause clinical adverse symptoms and mortality in any animal used in the acute and repeated-dose toxicity study. In addition, no significant changes were observed in body weight and internal organs, food and water intake, hematological and biochemical parameters, compared to control group. Therefore, these results provide an initial understanding regarding the toxicity profile of 7-acetoxy-4-aryl-3,4-dihydrocoumarin, which can be considered a neoflavonoid with toxicity seen at doses higher than 2000 mg/kg in Swiss mice.
• Synthetic and novel biocatalytic resolution studies on (±)-5/6/7-acetoxy-4-aryl-3,4-dihydrocoumarins
  作者：Ishwar Singh、Ashok K Prasad、Ajendra K Sharma、Rajendra K Saxena、Carl E Olsen、Ashok L Cholli、Lynne A Samuelson、Jayant Kumar、Arthur C Watterson、Virinder S Parmar

  DOI：10.1016/s0968-0896(02)00454-6

  日期：2003.2

  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.