(+/-)-3-hydroxymethyl-7-methoxy-3-methylchroman-4-one | 372486-20-9

• 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-hydroxymethyl-7-methoxy-3-methylchroman-4-one
• 英文别名: 7-methoxy-3-(hydroxymethyl)-3-methyl-chroman-4-one；Zuwjxyjttfgzde-uhfffaoysa-；3-(hydroxymethyl)-7-methoxy-3-methyl-2H-chromen-4-one
• CAS: 372486-20-9；372486-33-4；372486-45-8
• 化学式: C₁₂H₁₄O₄
• 分子量: 222.241
• InChiKey: ZUWJXYJTTFGZDE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  16
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.42
• 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-hydroxymethyl-7-methoxy-3-methylchroman-4-one 在 4-二甲氨基吡啶 作用下， 以 吡啶 为溶剂， 反应 18.0h， 以92%的产率得到(+/-)-3-acetoxymethyl-7-methoxy-3-methylchroman-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：

  2,4-二羟基苯丙酮 在 sodium hydroxide 、 potassium carbonate 作用下， 以 丙酮 为溶剂， 生成 (+/-)-3-hydroxymethyl-7-methoxy-3-methylchroman-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

文献信息

• Chemoenzymatic synthesis and resolution of compounds containing a quaternary stereocenters adjacent to a carbonyl group
  作者：Tridib Mahapatra、Nandan Jana、S. Nanda

  DOI：10.1016/j.tetasy.2008.04.024

  日期：2008.5

  Racemic compounds containing a quaternary stereocenter (having hydroxymethyl and alkyl group adjacent to keto functionality) based on chromanone, alpha-tetralone, and indalone scaffolds have been synthesized. An enzymatic irreversible transesterification approach has been applied to generate the pure enantiomers in a stereocontrolled fashion. The pure enantiomers of some alpha,alpha-dialkylated carbonyl compounds have been synthesized by this method. (C) 2008 Elsevier Ltd. All rights reserved.
• Synthesis and lipase-mediated stereoselective deacetylation of (±)-3-acetoxymethyl-3-alkyl-7-methoxychroman-4-ones
  作者：Poonam、Ashok K Prasad、Abul Azim、Rajesh Kumar、Subhash C Jain、Virinder S Parmar、Carl E Olsen、William Errington

  DOI：10.1016/s0040-4020(01)00698-6

  日期：2001.8

  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.

表征谱图