methyl 3-(2,2,5,5-tetramethyl-1,3-dioxolan-4-yl)propanoate | 1052108-42-5

• 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: methyl 3-(2,2,5,5-tetramethyl-1,3-dioxolan-4-yl)propanoate
• CAS: 1052108-42-5
• 化学式: C₁₁H₂₀O₄
• 分子量: 216.277
• InChiKey: MECSQTDOKSPXDH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.87
• 重原子数：
  15.0
• 可旋转键数：
  3.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.91
• 拓扑面积：
  44.76
• 氢给体数：
  0.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  methyl 3-(2,2,5,5-tetramethyl-1,3-dioxolan-4-yl)propanoate 、 苯硫酚 在 三甲基铝 作用下， 以 正己烷 、 二氯甲烷 为溶剂， 反应 0.33h， 以42%的产率得到S-phenyl 3-(2,2,5,5-tetramethyl-1,3-dioxolan-4-yl)propanethioate
  参考文献：
  名称：

  Direct Carbon−Carbon Bond Formation via Chemoselective Soft Enolization of Thioesters: A Remarkably Simple and Versatile Crossed-Claisen Reaction Applied to the Synthesis of LY294002

  摘要：

  Thioesters undergo chemoselective soft enolization and acylation by N-acylbenzotriazoles on treatment with MgBr(2)center dot OEt(2) and i-Pr(2)NEt to give beta-keto thioesters. Prior enolate formation is not required, and the reaction is conducted using untreated CH(2)Cl(2) open to the air. The coupled products are stable synthetic equivalents of beta-keto acids and can be converted directly into beta-keto esters, beta-keto amides, and beta-diketones under mild conditions. The utility of this carbon-carbon bond-forming method is shown through the synthesis of the PI3-K inhibitor LY294002.

  DOI：

  10.1021/ol801498u