2-(2,2-dimethyl-[1,3]dioxan-5-ylidene)-butyric acid ethyl ester | 496947-02-5

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: 2-(2,2-dimethyl-[1,3]dioxan-5-ylidene)-butyric acid ethyl ester
• 英文别名: Ethyl 2-(2,2-dimethyl-1,3-dioxan-5-ylidene)butanoate
• CAS: 496947-02-5
• 化学式: C₁₂H₂₀O₄
• 分子量: 228.288
• InChiKey: YTWGRFGGVKRQAZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.2
• 重原子数：
  16
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.75
• 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：

  2-(2,2-dimethyl-[1,3]dioxan-5-ylidene)-butyric acid ethyl ester 在 palladium on activated charcoal 盐酸 、 氢气 作用下， 以 甲醇 、 乙醇 为溶剂， 反应 19.17h， 生成 3-ethyl-4-methyl-2(5H)-furanone
  参考文献：
  名称：

  Selective Catalytic Hydrogenations and Hydrogenolyses VIII [1]: Stereoselective Synthesis of the Stereomeric Pilopyl Alcohols

  摘要：

  The stereoselective synthesis of pilopyl- and isopilopyl alcohol is reported. The reaction of dimethyldioxanone and diethoxyphosphoryl-butyric acid ethyl ester afforded the corresponding dioxanylidenbutyric acid ester as the key intermediate. Upon treatment with mineral acid it cyclized giving 3-ethyl-4-hydroxymethylfuran-2-one which in turn could be converted either to 3-ethyl-4-methylfuranone or pilopyl alcohol with excellent stereoselectivity and quantitative chemical yield. On the other hand, hydrogenation and subsequent cyclization of the same key compound furnished isopilopyl alcohol with good stereomeric purity and yield.

  DOI：

  10.1007/s00706-002-0484-9
• 作为产物：
  描述：

  2-膦酰丁酸三乙脂 、 2,2-二甲基-1,3-二恶烷-5-酮 在 sodium hydride 作用下， 以 四氢呋喃 为溶剂， 反应 1.5h， 生成 2-(2,2-dimethyl-[1,3]dioxan-5-ylidene)-butyric acid ethyl ester
  参考文献：
  名称：

  三和四取代的α，α'-链烯二醇的非酶几何选择性酰化

  摘要：

  已经开发出三和四取代的2-亚烷基-1，3-丙二醇的高度几何选择性有机催化酰化。各种四取代的2-亚烷基-1,3-丙二醇的高度E-选择性酰化是通过非酶法首次以96％至> 99％的选择性实现的。

  DOI：

  10.1002/adsc.201200242

文献信息

• Non-Enzymatic Geometry-Selective Acylation of Tri- and Tetrasubstituted α,α′-Alkenediols
  作者：Keisuke Yoshida、Kenji Mishiro、Yoshihiro Ueda、Takashi Shigeta、Takumi Furuta、Takeo Kawabata

  DOI：10.1002/adsc.201200242

  日期：2012.11.26

  A highly geometry-selective organocatalytic acylation of tri- and tetra-substituted 2-alkylidene-1,3-propanediols has been developed. The highly E-selective acylation of various tetrasubstituted 2-alkylidene-1,3-propanediols was achieved in 96 to >99% selectivity for the first time by a non-enzymatic protocol.

  已经开发出三和四取代的2-亚烷基-1，3-丙二醇的高度几何选择性有机催化酰化。各种四取代的2-亚烷基-1,3-丙二醇的高度E-选择性酰化是通过非酶法首次以96％至> 99％的选择性实现的。
• Selective Catalytic Hydrogenations and Hydrogenolyses VIII [1]: Stereoselective Synthesis of the Stereomeric Pilopyl Alcohols
  作者：Eberhard Reimann、Manfred Renz [2]、Helene Unger

  DOI：10.1007/s00706-002-0484-9

  日期：2002.9.1

  The stereoselective synthesis of pilopyl- and isopilopyl alcohol is reported. The reaction of dimethyldioxanone and diethoxyphosphoryl-butyric acid ethyl ester afforded the corresponding dioxanylidenbutyric acid ester as the key intermediate. Upon treatment with mineral acid it cyclized giving 3-ethyl-4-hydroxymethylfuran-2-one which in turn could be converted either to 3-ethyl-4-methylfuranone or pilopyl alcohol with excellent stereoselectivity and quantitative chemical yield. On the other hand, hydrogenation and subsequent cyclization of the same key compound furnished isopilopyl alcohol with good stereomeric purity and yield.

表征谱图