3-fluoro-3-oct-1-ynyl-dihydro-furan-2-one | 1092696-47-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 内酯类
• 英文名称: 3-fluoro-3-oct-1-ynyl-dihydro-furan-2-one
• 英文别名: 3-Fluoro-3-oct-1-ynyloxolan-2-one；3-fluoro-3-oct-1-ynyloxolan-2-one
• CAS: 1092696-47-3
• 化学式: C₁₂H₁₇FO₂
• 分子量: 212.264
• InChiKey: CVFXESQILVRNNK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  15
• 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：
  26.3
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  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72%的产率得到3-fluoro-3-oct-1-ynyl-dihydro-furan-2-one
  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).