2-fluoro-2,5-dimethylhex-3-ynoic acid ethyl ester | 1092696-42-8

• 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-fluoro-2,5-dimethylhex-3-ynoic acid ethyl ester
• 英文别名: Ethyl 2-fluoro-2,5-dimethylhex-3-ynoate；ethyl 2-fluoro-2,5-dimethylhex-3-ynoate
• CAS: 1092696-42-8
• 化学式: C₁₀H₁₅FO₂
• 分子量: 186.226
• InChiKey: PPOJTUZQWFASOE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  13
• 可旋转键数：
  3
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.7
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  ethyl 2,5-dimethylhexa-2,3-dienoate 在 lithium diisopropyl amide 、 N-氟代双苯磺酰胺 作用下， 以 四氢呋喃 为溶剂， 反应 0.5h， 以39%的产率得到2-fluoro-2,5-dimethylhex-3-ynoic acid ethyl ester
  参考文献：
  名称：

  Highly Regioselective Fluorination and Iodination of Alkynyl Enolates

  摘要：

  A simple yet efficient approach to various functionalized quaternary alpha-alkynyl alpha-fluoro esters and gamma-iodoallenoates from readily available allenoates through an alkynyl enolate intermediate generated by LDA is presented. Reaction of this alkynyl enolate with NFSI gives the alpha-product (alpha-alkynyl-alpha-fluoro ester), whereas the reaction of the silyl ether of alkynyl enolate with I-2 gives solely the gamma-product (iodoallenoate).

  DOI：

  10.1021/ol802451e

文献信息

• Highly Regioselective Fluorination and Iodination of Alkynyl Enolates
  作者：Han Yang、Bo Xu、Gerald B. Hammond

  DOI：10.1021/ol802451e

  日期：2008.12.18

  A simple yet efficient approach to various functionalized quaternary alpha-alkynyl alpha-fluoro esters and gamma-iodoallenoates from readily available allenoates through an alkynyl enolate intermediate generated by LDA is presented. Reaction of this alkynyl enolate with NFSI gives the alpha-product (alpha-alkynyl-alpha-fluoro ester), whereas the reaction of the silyl ether of alkynyl enolate with I-2 gives solely the gamma-product (iodoallenoate).