(E)-3-[3,4-(methylenedioxy)benzylidene]butyrolactone | 852676-78-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并间二氧杂环戊烯类
• 英文名称: (E)-3-[3,4-(methylenedioxy)benzylidene]butyrolactone
• 英文别名: (4E)-4-(1,3-benzodioxol-5-ylmethylidene)oxolan-2-one
• CAS: 852676-78-9
• 化学式: C₁₂H₁₀O₄
• 分子量: 218.209
• InChiKey: FGNVVBFXOXIUDH-YCRREMRBSA-N

物化性质

• 沸点：
  430.7±34.0 °C(Predicted)
• 密度：
  1.405±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  16
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  44.8
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (E)-3-[3,4-(methylenedioxy)benzylidene]butyrolactone 在 palladium dihydroxide 、 palladium on activated charcoal lithium aluminium tetrahydride 、 Candida rugosa lipase AY 、 氢气 、 溶剂黄146 、 lithium diisopropyl amide 作用下， 以 四氢呋喃 为溶剂， -30.0~20.0 ℃ 、101.33 kPa 条件下， 反应 74.5h， 生成 threo-(-)-2,3-bis(3',4'-methylenedioxybenzyl)-1,4-butanediol monoacetate
  参考文献：
  名称：

  Lipase‐Catalyzed Esterification of a (±)‐2,3‐Di(Arylmethyl)‐1,4‐butanediol and Its Application to the Synthesis of (S,S)‐(+)‐Hinokinin

  摘要：

  Racemic trans-2,3-di[(3,4-methylenedioxy)benzyl]-1,4-butanediol (dihydrocubebin) 6 was enantioselectively esterified using lipases as catalysts with vinyl acetate. Optically active (SS)-1,4-butanediol 6 obtained was selectively oxygenated with a Fetizon reagent, affording (SS)-(+)-hinokinin 9 in a high yield.

  DOI：

  10.1081/scc-200051037
• 作为产物：
  描述：

  (Z)-4-(苯并[d][1,3]二氧代l-5-基)-3-(乙氧基羰基)丁3-烯酸 在 氢氧化钾 、 sodium tetrahydroborate 、 calcium chloride 作用下， 以 乙醇 为溶剂， 反应 3.0h， 以85%的产率得到(E)-3-[3,4-(methylenedioxy)benzylidene]butyrolactone
  参考文献：
  名称：

  Lipase‐Catalyzed Esterification of a (±)‐2,3‐Di(Arylmethyl)‐1,4‐butanediol and Its Application to the Synthesis of (S,S)‐(+)‐Hinokinin

  摘要：

  Racemic trans-2,3-di[(3,4-methylenedioxy)benzyl]-1,4-butanediol (dihydrocubebin) 6 was enantioselectively esterified using lipases as catalysts with vinyl acetate. Optically active (SS)-1,4-butanediol 6 obtained was selectively oxygenated with a Fetizon reagent, affording (SS)-(+)-hinokinin 9 in a high yield.

  DOI：

  10.1081/scc-200051037

文献信息

• Lipase‐Catalyzed Esterification of a (±)‐2,3‐Di(Arylmethyl)‐1,4‐butanediol and Its Application to the Synthesis of (<i>S</i>,<i>S</i>)‐(+)‐Hinokinin
  作者：Toshiaki Morimoto、Hazuki Nagai、Kazuo Achiwa

  DOI：10.1081/scc-200051037

  日期：2005.3

  Racemic trans-2,3-di[(3,4-methylenedioxy)benzyl]-1,4-butanediol (dihydrocubebin) 6 was enantioselectively esterified using lipases as catalysts with vinyl acetate. Optically active (SS)-1,4-butanediol 6 obtained was selectively oxygenated with a Fetizon reagent, affording (SS)-(+)-hinokinin 9 in a high yield.