(+/-)-3-butyl-3-hydroxymethyl-7-methoxychroman-4-one | 372486-24-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并吡喃
• 英文名称: (+/-)-3-butyl-3-hydroxymethyl-7-methoxychroman-4-one
• 英文别名: 3-butyl-3-(hydroxymethyl)-7-methoxy-2H-chromen-4-one
• CAS: 372486-24-3；372486-37-8；372486-49-2
• 化学式: C₁₅H₂₀O₄
• 分子量: 264.321
• InChiKey: GMEMVVHLYFFKNW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  19
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.53
• 拓扑面积：
  55.8
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  乙酸酐 、 (+/-)-3-butyl-3-hydroxymethyl-7-methoxychroman-4-one 在 4-二甲氨基吡啶 作用下， 以 吡啶 为溶剂， 反应 18.0h， 以96%的产率得到(+/-)-3-acetoxymethyl-3-butyl-7-methoxychroman-4-one
  参考文献：
  名称：

  Synthesis and lipase-mediated stereoselective deacetylation of (±)-3-acetoxymethyl-3-alkyl-7-methoxychroman-4-ones

  摘要：

  Six (+/-)-3-acetoxymethyl-3-alkyl-7-methoxychroman-4-ones have been synthesized in four steps starting with the coupling of resorcinol with corresponding aliphatic acid leading to the formation of 2,4-dihydroxyphenyl alkyl ketones, which upon monomethylation and hydroxymethylation, followed by acetylation afforded the racemic acetoxymethylated compounds in 17-30% overall yields. Candida rugosa lipase-catalyzed deacetylation of (+/-)-3-acetoxymethylchromanones in diisopropyl ether exhibited fairly moderate enantioselectivity. (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(01)00698-6
• 作为产物：
  描述：

  2’,4’-二羟基苯己酮 在 sodium hydroxide 、 potassium carbonate 作用下， 以 丙酮 为溶剂， 生成 (+/-)-3-butyl-3-hydroxymethyl-7-methoxychroman-4-one
  参考文献：
  名称：

  Synthesis and lipase-mediated stereoselective deacetylation of (±)-3-acetoxymethyl-3-alkyl-7-methoxychroman-4-ones

  摘要：

  Six (+/-)-3-acetoxymethyl-3-alkyl-7-methoxychroman-4-ones have been synthesized in four steps starting with the coupling of resorcinol with corresponding aliphatic acid leading to the formation of 2,4-dihydroxyphenyl alkyl ketones, which upon monomethylation and hydroxymethylation, followed by acetylation afforded the racemic acetoxymethylated compounds in 17-30% overall yields. Candida rugosa lipase-catalyzed deacetylation of (+/-)-3-acetoxymethylchromanones in diisopropyl ether exhibited fairly moderate enantioselectivity. (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(01)00698-6