Ethyl 2-allyl-3,3-(1,3-propanedioxy)butanoate | 133885-02-6

• 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: Ethyl 2-allyl-3,3-(1,3-propanedioxy)butanoate
• 英文别名: Ethyl 2-(2-methyl-1,3-dioxan-2-yl)pent-4-enoate
• CAS: 133885-02-6
• 化学式: C₁₂H₂₀O₄
• 分子量: 228.288
• InChiKey: SLSPMRZWRQWCJJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  16
• 可旋转键数：
  6
• 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：

  Ethyl 2-allyl-3,3-(1,3-propanedioxy)butanoate 在 三氟甲磺酸三甲基硅酯 、 dimethyl sulfide borane 作用下， 以 二氯甲烷 为溶剂， 生成 Ethyl 2-allyl-3-(3-hydroxypropoxy)butanoate
  参考文献：
  名称：

  A selectivity study of activated ketal reduction with borane dimethyl sulfide

  摘要：

  A chemo- and regioselectivity study of the reagent combination BH3.SMe2/TMSOTf for ketal reduction has been undertaken. It has revealed that simple 1,3-dioxanes reduce cleanly at low temperature in CH2Cl2 while simple 1,3-dioxolanes may give complete ring cleavage and dimerization products. A study of reduction of 4-substituted 1,3-dioxolanes has revealed a solvent-directed regioselectivity which in THF favors the secondary protected derivative. A mechanism is postulated to account for the selectivities based on recent thinking on acetal substitution reactions.

  DOI：

  10.1021/jo00076a041
• 作为产物：
  描述：

  2-乙酰基-4-戊酸乙酯 生成 Ethyl 2-allyl-3,3-(1,3-propanedioxy)butanoate
  参考文献：
  名称：

  Bartels Birgit, Hunter Roger, J. Org. Chem, 58 (1993) N 24, S 6756-6765

  摘要：

  DOI：

文献信息

• Reduction of activated ketals with borane-dimethyl sulphide
  作者：Roger Hunter、Birgit Bartels、Joseph P. Michael

  DOI：10.1016/s0040-4039(00)74497-2

  日期：1991.2

  Borane-Dimethyl sulphide reduces ketals activated with TMSOTf at -78-degrees-C in dichloromethane. The scope and selectivity of the reagent has been investigated.