1,1,1-Trifluoro-5-methyl-2-octyn-4-ol

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 1,1,1-Trifluoro-5-methyl-2-octyn-4-ol
• 英文别名: 1,1,1-Trifluoro-5-methyloct-2-yn-4-ol
• 化学式: C₉H₁₃F₃O
• 分子量: 194.197
• InChiKey: WSQMXVTVRMFOPA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  13
• 可旋转键数：
  3
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.78
• 拓扑面积：
  20.2
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  2-甲基戊醛 、 2-溴-3,3,3-三氟丙烯 在 lithium diisopropyl amide 作用下， 以 四氢呋喃 为溶剂， 以74.9%的产率得到1,1,1-Trifluoro-5-methyl-2-octyn-4-ol
  参考文献：
  名称：

  Modified Preparation Method of Trifluoromethylated Propargylic Alcohols and Its Application to Chiral 2,6-Dideoxy-6,6,6-trifluoro sugars

  摘要：

  Convenient generation of 3,3,3-trifluoropropynyl anion was realized from 2-bromo-3,3,3-trifluoropropene, and the anion's reaction with various electrophiles proceeded in excellent isolated yields. One of the pro ducts, 1-(benzyloxy)-6,6,6-trifluoro-4-hexyn-3-ol (4b), was further employed for the diastereoselective construction of 2,6-dideoxy-6,6,6-trifluorosugars after enzymatic optical resolution and osmium dihydroxylation of the corresponding olefins. The strongly electron-withdrawing trifluoromethyl moiety, significantly affecting the nucleophilic nature of neighboring functionalities, allows the ready differentiation of hydroxy groups by routine chemical transformation, which results in the shortening of the reaction sequence.

  DOI：

  10.1021/jo00124a013