1,1,1-trifluoro-2-methyl-4-(7-oxabicyclo[4.1.0]hept-1-yl)but-3-yn-2-ol

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 氧杂环己烷
• 英文名称: 1,1,1-trifluoro-2-methyl-4-(7-oxabicyclo[4.1.0]hept-1-yl)but-3-yn-2-ol
• 英文别名: 1,1,1-Trifluoro-2-methyl-4-(7-oxabicyclo[4.1.0]heptan-1-yl)but-3-yn-2-ol；1,1,1-trifluoro-2-methyl-4-(7-oxabicyclo[4.1.0]heptan-1-yl)but-3-yn-2-ol
• 化学式: C₁₁H₁₃F₃O₂
• 分子量: 234.218
• InChiKey: JDBHATALYKIWTP-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：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.82
• 拓扑面积：
  32.8
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  1,1,1-trifluoro-2-methyl-4-(7-oxabicyclo[4.1.0]hept-1-yl)but-3-yn-2-ol 在 1,3-dimesityl-4,5-dihydro-3H-imidazol-1-ium chloride copper(l) chloride 、 sodium t-butanolate 作用下， 以 甲苯 为溶剂， 反应 0.5h， 以50%的产率得到
  参考文献：
  名称：

  小但有效：氢化铜催化合成α-羟基丙二烯。

  摘要：

  DOI：

  10.1002/anie.200603739
• 作为产物：
  描述：

  6-乙炔基-7-氧杂双环[4.1.0]庚烷 、 1,1,1-三氟丙酮 在 正丁基锂 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 反应 0.25h， 以57%的产率得到1,1,1-trifluoro-2-methyl-4-(7-oxabicyclo[4.1.0]hept-1-yl)but-3-yn-2-ol
  参考文献：
  名称：

  高官能化炔丙醇的合成：将环氧乙炔直接添加到醛和酮中

  摘要：

  Direct nucleophilic addition of terminal alkynes comprising an epoxy group to aldehydes and ketones is reported with BuLi or lithium diisopropylamide for the generation of the corresponding lithium acetylides. This alkynylation reaction tolerates a wide variety of different functional groups (e.g.. alcohols. silyl ethers. halides, double bonds) in the carbonyl compound, as well as in the acetylenic nucleophile, and furnishes highly functionalized propargylic alcohols in good-to-excel lent yields. The method is particularly useful for the regioselective introduction of an epoxide function into multiply unsaturated target molecules.

  DOI：

  10.1002/1522-2675(200210)85:10<3176::aid-hlca3176>3.0.co;2-7

文献信息

• Synthesis of Highly Functionalized Propargylic Alcohols: Direct Addition of Epoxy Acetylides to Aldehydes and Ketones
  作者：Anja Hoffmann-Röder、Norbert Krause

  DOI：10.1002/1522-2675(200210)85:10<3176::aid-hlca3176>3.0.co;2-7

  日期：2002.10

  Direct nucleophilic addition of terminal alkynes comprising an epoxy group to aldehydes and ketones is reported with BuLi or lithium diisopropylamide for the generation of the corresponding lithium acetylides. This alkynylation reaction tolerates a wide variety of different functional groups (e.g.. alcohols. silyl ethers. halides, double bonds) in the carbonyl compound, as well as in the acetylenic nucleophile, and furnishes highly functionalized propargylic alcohols in good-to-excel lent yields. The method is particularly useful for the regioselective introduction of an epoxide function into multiply unsaturated target molecules.
• Small but Effective: Copper Hydride Catalyzed Synthesis of α-Hydroxyallenes
  作者：Carl Deutsch、Bruce H. Lipshutz、Norbert Krause

  DOI：10.1002/anie.200603739

  日期：2007.2.26