cis-5-isopropyl-3-methylene-4-phenyldihydrofuran-2-one

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 内酯类
• 英文名称: cis-5-isopropyl-3-methylene-4-phenyldihydrofuran-2-one
• 英文别名: (4R,5R)-3-methylidene-4-(2-phenylethyl)-5-propan-2-yloxolan-2-one
• 化学式: C₁₆H₂₀O₂
• 分子量: 244.334
• InChiKey: BCILXCBVYYDSJP-HUUCEWRRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.3
• 重原子数：
  18
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.44
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  4-phenyl-1,1-dibromo-1-butene 在 1,3-bis[(diphenylphosphino)propane]dichloronickel(II) 、 四氯化钛 、 三乙胺 作用下， 以 四氢呋喃 、 乙醚 、 二氯甲烷 为溶剂， 反应 0.58h， 生成 cis-5-isopropyl-3-methylene-4-phenyldihydrofuran-2-one
  参考文献：
  名称：

  Synthesis and Reaction of Bromoallylsilane: A Short Access to β,γ-Disubstituted α-Methylene-γ-butyrolactone

  摘要：

  (Z)-beta-Bromoallylsilanes (1a-c) were prepared by a stereoselective Ni-catalyzed cross-coupling reaction of 1,1-dibromo-4-phenylbutene (4) with silylmethylmagnesium halide. Sakurai-Hosomi reaction of la with aldehyde gave syn-3-alkyl-2-bromo-4-hydroxyalkene (2a, 2c, and 2c) and that with acetal gave syn-4-alkoxy-3-alkyl-2-bromoalkene (2b and 2d) stereoselectively. The products with formyl function reacted with a Ni-carbonyl complex to give beta,gamma-disubstituted (alpha-methylene-gamma-butyrolactones (3) in good yields. Pd-catalyzed cross-coupling reaction of la-c or 4 with silylmethylmagnesium halide gave 1, 1-bis(silylmethyl)-1-alkenes (1d-i), which reacted with dimethyl acetal to generate more functionalized allylsilane (6).

  DOI：

  10.3987/com-03-s52

文献信息

• Synthesis and Reaction of Bromoallylsilane: A Short Access to β,γ-Disubstituted α-Methylene-γ-butyrolactone
  作者：Jun'ichi Uenishi、Masashi Ohmi

  DOI：10.3987/com-03-s52

  日期：——

  (Z)-beta-Bromoallylsilanes (1a-c) were prepared by a stereoselective Ni-catalyzed cross-coupling reaction of 1,1-dibromo-4-phenylbutene (4) with silylmethylmagnesium halide. Sakurai-Hosomi reaction of la with aldehyde gave syn-3-alkyl-2-bromo-4-hydroxyalkene (2a, 2c, and 2c) and that with acetal gave syn-4-alkoxy-3-alkyl-2-bromoalkene (2b and 2d) stereoselectively. The products with formyl function reacted with a Ni-carbonyl complex to give beta,gamma-disubstituted (alpha-methylene-gamma-butyrolactones (3) in good yields. Pd-catalyzed cross-coupling reaction of la-c or 4 with silylmethylmagnesium halide gave 1, 1-bis(silylmethyl)-1-alkenes (1d-i), which reacted with dimethyl acetal to generate more functionalized allylsilane (6).