5-hydroxy-2,2-dimethyl-1-phenyl-4,5-bis(trifluoromethyl)-3-pentanone

• 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: 5-hydroxy-2,2-dimethyl-1-phenyl-4,5-bis(trifluoromethyl)-3-pentanone
• 英文别名: (4S,5R)-6,6,6-trifluoro-5-hydroxy-2,2-dimethyl-1-phenyl-4-(trifluoromethyl)hexan-3-one
• 化学式: C₁₅H₁₆F₆O₂
• 分子量: 342.281
• InChiKey: VBWKCPLBWMUYKL-ZYHUDNBSSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.3
• 重原子数：
  23
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.53
• 拓扑面积：
  37.3
• 氢给体数：
  1
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  5-hydroxy-2,2-dimethyl-1-phenyl-4,5-bis(trifluoromethyl)-3-pentanone 在 三氯化铝 、 dimethyl sulfide borane 作用下， 以 四氢呋喃 、 乙醚 为溶剂， 反应 2.5h， 生成 4-(1,1-dimethyl-2-phenylethyl)-2,2-dimethyl-5,6-bis(trifluoromethyl)-[1,3]dioxane
  参考文献：
  名称：

  Dipole Interaction-Controlled Stereoselectivity in Aldol Reaction of α-CF₃ Enolate with Fluoral

  摘要：

  [GRAPHICS]The stereoselectivity of a reaction is generally determined by minimizing steric repulsion. However, the aldol reaction of alpha-CF3-ketone (Z)-enolate with fluoral anomalously gave an anti-aldol through a sterically demanding transition state, because of the strong dipole interaction of the two CF3 groups. We have thus disclosed a paradigm shift from steric to electronic control of reaction stereoselectivity.

  DOI：

  10.1021/ol0358307
• 作为产物：
  描述：

  2,2,2-三氟乙醛 、 1,1,1-trifluoro-4,4,-dimethyl-5-phenyl-3-pentanone 在 三正丁胺 、 四氯化钛 作用下， 以 二氯甲烷 为溶剂， 反应 4.25h， 以83%的产率得到5-hydroxy-2,2-dimethyl-1-phenyl-4,5-bis(trifluoromethyl)-3-pentanone
  参考文献：
  名称：

  Dipole Interaction-Controlled Stereoselectivity in Aldol Reaction of α-CF₃ Enolate with Fluoral

  摘要：

  [GRAPHICS]The stereoselectivity of a reaction is generally determined by minimizing steric repulsion. However, the aldol reaction of alpha-CF3-ketone (Z)-enolate with fluoral anomalously gave an anti-aldol through a sterically demanding transition state, because of the strong dipole interaction of the two CF3 groups. We have thus disclosed a paradigm shift from steric to electronic control of reaction stereoselectivity.

  DOI：

  10.1021/ol0358307