4-methyl-2-(3-trifluoromethyl-phenyl)-pent-4-en-2-ol

• 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: 4-methyl-2-(3-trifluoromethyl-phenyl)-pent-4-en-2-ol
• 英文别名: (2R)-4-methyl-2-[3-(trifluoromethyl)phenyl]pent-4-en-2-ol
• 化学式: C₁₃H₁₅F₃O
• 分子量: 244.257
• InChiKey: SSSGLPZCTAXDMF-GFCCVEGCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  17
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  20.2
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  4-methyl-2-(3-trifluoromethyl-phenyl)-pent-4-en-2-ol 在 臭氧 、 二甲基硫 作用下， 以 二氯甲烷 为溶剂， 生成 (R)-4-Hydroxy-4-(3-trifluoromethyl-phenyl)-pentan-2-one
  参考文献：
  名称：

  Catalytic Asymmetric Methallylation of Ketones with an (H₈-BINOLate)Ti-Based Catalyst

  摘要：

  The first catalytic asymmetric methallylation of ketones is reported. The catalyst, which is generated from titanium tetraisopropoxide, H-8-BINOL, 2-propanol, and tetramethallylstannane, reacts with ketones in acetonitrile to afford tertiary homoallylic alcohols in fair to excellent yields (55-99%) and fair to high enantioselectivities (46-90%). Ozonolysis of the resulting products provides access to chiral, ss-hydroxy ketones, which are not readily prepared from direct asymmetric aldol reaction of acetone with ketones.

  DOI：

  10.1021/ol061417y
• 作为产物：
  描述：

  间三氟甲基苯乙酮 、 四(2-甲基丙-2-烯基)锡烷 在 titanium(IV) isopropylate 、 (R)-5,5',6,6',7,7',8,8'-八氢-[1,1'-联萘]-2,2'-二酚 异丙醇 作用下， 以 乙腈 为溶剂， 反应 18.0h， 生成 4-methyl-2-(3-trifluoromethyl-phenyl)-pent-4-en-2-ol 、 4-methyl-2-(3-trifluoromethyl-phenyl)-pent-4-en-2-ol
  参考文献：
  名称：

  Catalytic Asymmetric Methallylation of Ketones with an (H₈-BINOLate)Ti-Based Catalyst

  摘要：

  The first catalytic asymmetric methallylation of ketones is reported. The catalyst, which is generated from titanium tetraisopropoxide, H-8-BINOL, 2-propanol, and tetramethallylstannane, reacts with ketones in acetonitrile to afford tertiary homoallylic alcohols in fair to excellent yields (55-99%) and fair to high enantioselectivities (46-90%). Ozonolysis of the resulting products provides access to chiral, ss-hydroxy ketones, which are not readily prepared from direct asymmetric aldol reaction of acetone with ketones.

  DOI：

  10.1021/ol061417y

文献信息

• Catalytic Asymmetric Methallylation of Ketones with an (H₈-BINOLate)Ti-Based Catalyst
  作者：Jeung Gon Kim、Elizabeth H. Camp、Patrick J. Walsh

  DOI：10.1021/ol061417y

  日期：2006.9.1

  The first catalytic asymmetric methallylation of ketones is reported. The catalyst, which is generated from titanium tetraisopropoxide, H-8-BINOL, 2-propanol, and tetramethallylstannane, reacts with ketones in acetonitrile to afford tertiary homoallylic alcohols in fair to excellent yields (55-99%) and fair to high enantioselectivities (46-90%). Ozonolysis of the resulting products provides access to chiral, ss-hydroxy ketones, which are not readily prepared from direct asymmetric aldol reaction of acetone with ketones.