(4R)-4-Acetoxy-6-(benzyloxy)-1,1,1-trifluoro-2-hexyne | 161987-48-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: (4R)-4-Acetoxy-6-(benzyloxy)-1,1,1-trifluoro-2-hexyne
• 英文别名: [(3R)-6,6,6-trifluoro-1-phenylmethoxyhex-4-yn-3-yl] acetate
• CAS: 161987-48-0
• 化学式: C₁₅H₁₅F₃O₃
• 分子量: 300.278
• InChiKey: SXHASVLASCOLTM-AWEZNQCLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  21
• 可旋转键数：
  7
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  35.5
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  (4R)-4-Acetoxy-6-(benzyloxy)-1,1,1-trifluoro-2-hexyne 在 potassium carbonate 作用下， 以 甲醇 为溶剂， 反应 0.5h， 以95.9%的产率得到(3R)-1-(Benzyloxy)-6,6,6-trifluoro-4-hexyn-3-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
• 作为产物：
  描述：

  3-苄氧基丙醛 在 lithium diisopropyl amide 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 反应 12.58h， 生成 (4R)-4-Acetoxy-6-(benzyloxy)-1,1,1-trifluoro-2-hexyne
  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

文献信息

• Novel stereoselective syntheses of chiral 2,6-dideoxy-6,6,6-trifluoro sugars via enzymatic resolution of trifluoromethylated propynylic alcohol
  作者：Kenji Mizutani、Takashi Yamazaki、Tomoya Kitazume

  DOI：10.1039/c39950000051

  日期：——

  All stereoisomers of homochiral 2,6-dideoxy-6,6,6-trifluoro sugars are conventionally synthesized from the same optically pure CF3-containing propynylic alcohol via the novel one-pot reaction of 2-bromo-3,3,3-trifluoropropene, followed by optical resolution by enzymatic esterification.

  通常通过相同的光学纯的含CF 3的丙炔醇通过新颖的2-溴-3,3,3-一锅反应合成高手性2,6-二脱氧-6,6,6-三氟糖的所有立体异构体。三氟丙烯，然后通过酶促酯化进行光学拆分。