4-(hydroxymethyl)-3-(2-methyl-1-phenylpropyl)tetrahydrofuran-2-one | 143994-30-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 4-(hydroxymethyl)-3-(2-methyl-1-phenylpropyl)tetrahydrofuran-2-one
• 英文别名: (3S,4R)-4-(hydroxymethyl)-3-(2-methyl-1-phenylpropyl)oxolan-2-one
• CAS: 143994-30-3
• 化学式: C₁₅H₂₀O₃
• 分子量: 248.322
• InChiKey: OFTMNCRPEWGKFG-WYAMFQBQSA-N

物化性质

• 沸点：
  410.0±18.0 °C(Predicted)
• 密度：
  1.109±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  18
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.53
• 拓扑面积：
  46.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  (E)-1-ethyl 4-hydrogen 2-(2-methyl-1-phenylpropylidene)succinate 在 palladium on activated charcoal sodium periodate 、 dimethyl sulfide borane 、 氢气 作用下， 以 四氢呋喃 、 甲醇 、 水 、 溶剂黄146 、 甲苯 为溶剂， 反应 14.0h， 生成 4-(hydroxymethyl)-3-(2-methyl-1-phenylpropyl)tetrahydrofuran-2-one
  参考文献：
  名称：

  A Breakthrough for the Photochemical Arylation in the 3-(Phenylmethyl)-2(5H)-furanone system Leading to the Tetrahydroindenofuranone System

  摘要：

  The photochemistry of the 'central methane'-substituted 3-benzyl-2(5H)-furanone system (1) is described. Despite its di-pi-methane structure, photochemical arylation was found to predominate in place of the di-pi-methane rearrangement, and gave substituted tetrahydroindenofuranones (2) in good yields.

  DOI：

  10.3987/com-92-6034

文献信息

• A Breakthrough for the Photochemical Arylation in the 3-(Phenylmethyl)-2(5H)-furanone system Leading to the Tetrahydroindenofuranone System
  作者：Osamu Muraoka、Genzoh Tanabe、Kyoko Sano、Takefumi Momose

  DOI：10.3987/com-92-6034

  日期：——

  The photochemistry of the 'central methane'-substituted 3-benzyl-2(5H)-furanone system (1) is described. Despite its di-pi-methane structure, photochemical arylation was found to predominate in place of the di-pi-methane rearrangement, and gave substituted tetrahydroindenofuranones (2) in good yields.
• Furan-2(3H)- and 2(5H)-ones. Part 5. Photoreactions of 3-benzylfuran2(5H)-ones; cyclisation to indenofuranones
  作者：Osamu Muraoka、Genzoh Tanabe、Kyohko Sano、Toshie Minematsu、Takefumi Momose

  DOI：10.1039/p19940001833

  日期：——

  The effect of substitution at the 'central methane' on the photoreactivity of 3-benzylfuran-2(5H)ones 5a-g was investigated. Despite its di-pi-methane structure, photochemical arylation was effected to give substituted indenofuranones 6 in good yields. Only the substitution by phenyl caused the di-pi-methane rearrangement to give a cyclopropanofuranone 18g in moderate yield.