3-benzyloxycarbonyl-6-methoxy-3-methylchroman-4-one | 646064-65-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并噁庚英
• 英文名称: 3-benzyloxycarbonyl-6-methoxy-3-methylchroman-4-one
• 英文别名: benzyl 6-methoxy-3-methyl-4-oxo-2H-chromene-3-carboxylate
• CAS: 646064-65-5
• 化学式: C₁₉H₁₈O₅
• 分子量: 326.349
• InChiKey: CWQNQNHTGSIFIO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  24
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.26
• 拓扑面积：
  61.8
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  3-benzyloxycarbonyl-6-methoxy-3-methylchroman-4-one 在 钯 (1R,2R,3S,4S)-3-Amino-1,7,7-trimethyl-bicyclo[2.2.1]heptan-2-ol 、 氢气 作用下， 以 乙酸乙酯 为溶剂， 反应 8.5h， 生成 (R)-6-methoxy-3-methyl-4-chromanone 、 (S)-6-methoxy-3-methyl-4-chromanone
  参考文献：
  名称：

  Access to racemic and enantioenriched 3-methyl-4-chromanones: catalysed asymmetric protonation of corresponding enolic species as the key step

  摘要：

  Bronsted acids induced the intramolecular cyclisation of 3-aryloxypropanoic esters affording 3-methyl-4-chromanones, which have been transformed into the corresponding racemic benzyl beta-oxoesters. These latter esters, in the presence of hydrogen and catalytic amounts of both palladium and (endo, endo) aminobomeol, led to optically active chromanones with up to 75% ee through a deprotection-decarboxylation-protonation cascade reaction. (C) 2003 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2003.09.095
• 作为产物：
  描述：

  3-(4-甲氧基苯氧基)-2-甲基丙酸乙酯 在 甲烷磺酸 、 lithium hexamethyldisilazane 作用下， 以 四氢呋喃 、 正己烷 、 甲苯 为溶剂， 反应 5.0h， 生成 3-benzyloxycarbonyl-6-methoxy-3-methylchroman-4-one
  参考文献：
  名称：

  Access to racemic and enantioenriched 3-methyl-4-chromanones: catalysed asymmetric protonation of corresponding enolic species as the key step

  摘要：

  Bronsted acids induced the intramolecular cyclisation of 3-aryloxypropanoic esters affording 3-methyl-4-chromanones, which have been transformed into the corresponding racemic benzyl beta-oxoesters. These latter esters, in the presence of hydrogen and catalytic amounts of both palladium and (endo, endo) aminobomeol, led to optically active chromanones with up to 75% ee through a deprotection-decarboxylation-protonation cascade reaction. (C) 2003 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2003.09.095