2-hydroxy-2-methyl-4-phenyl-1,1,1-trifluorobut-3-ene | 247912-54-5

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 肉桂醇
• 英文名称: 2-hydroxy-2-methyl-4-phenyl-1,1,1-trifluorobut-3-ene
• 英文别名: (E)-1,1,1-trifluoro-2-methyl-4-phenylbut-3-en-2-ol
• CAS: 247912-54-5
• 化学式: C₁₁H₁₁F₃O
• 分子量: 216.203
• InChiKey: CLRVQZYMDAOWKZ-BQYQJAHWSA-N

物化性质

• 沸点：
  284.3±40.0 °C(Predicted)
• 密度：
  1.218±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  15
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.27
• 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：

  1-辛硫醇 、 2-hydroxy-2-methyl-4-phenyl-1,1,1-trifluorobut-3-ene 在 三氟化硼乙醚 作用下， 以 二氯甲烷 为溶剂， 反应 24.25h， 以100%的产率得到(E)-2-methyl-4-octylthio-4-phenyl-1,1,1-trifluoro-2-butene
  参考文献：
  名称：

  由 α-(三氟甲基)烯丙醇制备的三氟甲基化乙烯基和芳香族化合物

  摘要：

  α-(三氟甲基)烯丙醇很容易从 α,β-不饱和羰基化合物中获得，很容易转化为 γ-(三氟甲基)烯丙基硫醚、苄基醚、三氟乙酸酯和叠氮化物。羟基官能团的 γ 位上的苯基取代基增强了它们的反应性和 SN 2' 或 SN 1' 取代的容易程度，而 u 位上的苯环允许 BF 3 介导的 (三氟甲基) 茚的合成。4-烷基-4-甲氧基-1-(三氟甲基)环六-2,5-二烯醇，很容易从4-烷基苯酚中获得，很容易转化为带有亲核取代基(MeO，Cl)的4-烷基(三氟甲基)苯。环或苄基位置。

  DOI：

  10.1055/s-2004-815928
• 作为产物：
  描述：

  trans-4,4,4-trifluoro-3-methyl-1-pehnyl-3-trimethylsilyloxy-1-butene 在 盐酸 作用下， 以 四氢呋喃 为溶剂， 反应 3.0h， 以98%的产率得到2-hydroxy-2-methyl-4-phenyl-1,1,1-trifluorobut-3-ene
  参考文献：
  名称：

  CsF-Catalyzed Nucleophilic Trifluoromethylation of trans-Enones with Trimethyl(trifluoromethyl)silane:  A Facile Synthesis of trans-α-Trifluoromethyl Allylic Alcohols

  摘要：

  [GRAPHICS]Reactions of trans-enones, R-C=C-COR' (R = Ph, Me, -C=CH-CH=C-S; R' = Ph, Me, Pt, CFB) (la-e), with TMS-CF3 in the presence of catalytic amounts of cesium fluoride (CsF) in ethylene glycol dimethyl ether led to the formation of the corresponding trans-alpha-trifluoromethyl silyl ethers, R-C=C-C(OSiMe3)(CF3)R' (R = Ph, Me, -C=CH-CH=C-S; R' = Ph, Me, Pt, CFB) (2a-e), in essentially quantitative yield. On hydrolysis with aqueous HCl, the corresponding trans-alpha-trifluaromethyl allylic alcohols, R-C=C-C(OH)(CF3)R' (R = Ph, Me, -C=CH-CH=C-S; R' = Ph, Me, Et, CF3) (3a-e), were formed in >90% isolated yield. Under similar reaction conditions, 2-cyclohexen-1-one (1f) also gave trifluoromethyl allylic alcohols (3f) in 92% yield. The intermediates (2a-f) and products (3a-f) are liquids and were characterized by IR, H-1, (19)f and C-13 NMR, MS, and high-resolution mass spectroscopy (HRMS).

  DOI：

  10.1021/ol990844r

文献信息

• Synthesis of αβ-Unsaturated Trifluoromethyl Ketones from 4-Dimethylamino-1,1,1-trifluorobut-3-ene-2-one by Addition of Grignard Reagents
  作者：Rebecca J. Andrew、John M. Mellor

  DOI：10.1016/s0040-4020(00)00597-4

  日期：2000.9

  such as dimethylamine and they react with Grignard reagents to give αβ-unsaturated trifluoromethyl ketones in good yield by 1,4-addition followed by elimination. The generality of this procedure is contrasted with reactions based either on the use of organolithium nucleophiles, or the use of 4-alkoxy-αβ-unsaturated trifluoromethyl ketones as electrophilic partners.

  通过4-乙氧基-1,1,1-三氟丁-3-烯-2-酮与胺（如二甲胺）反应可获得烯胺酮，它们与格氏试剂反应生成αβ-不饱和三氟甲基酮，产率高，产率为1,4。 -添加，然后消除。该方法的一般性与基于使用有机锂亲核试剂或基于4-烷氧基-αβ-不饱和三氟甲基酮作为亲电子试剂的反应形成对比。
• CsF-Catalyzed Nucleophilic Trifluoromethylation of <i>trans</i>-Enones with Trimethyl(trifluoromethyl)silane:  A Facile Synthesis of <i>trans</i>-α-Trifluoromethyl Allylic Alcohols
  作者：Rajendra P. Singh、Robert L. Kirchmeier、Jean'ne M. Shreeve

  DOI：10.1021/ol990844r

  日期：1999.10.1

  [GRAPHICS]Reactions of trans-enones, R-C=C-COR' (R = Ph, Me, -C=CH-CH=C-S; R' = Ph, Me, Pt, CFB) (la-e), with TMS-CF3 in the presence of catalytic amounts of cesium fluoride (CsF) in ethylene glycol dimethyl ether led to the formation of the corresponding trans-alpha-trifluoromethyl silyl ethers, R-C=C-C(OSiMe3)(CF3)R' (R = Ph, Me, -C=CH-CH=C-S; R' = Ph, Me, Pt, CFB) (2a-e), in essentially quantitative yield. On hydrolysis with aqueous HCl, the corresponding trans-alpha-trifluaromethyl allylic alcohols, R-C=C-C(OH)(CF3)R' (R = Ph, Me, -C=CH-CH=C-S; R' = Ph, Me, Et, CF3) (3a-e), were formed in >90% isolated yield. Under similar reaction conditions, 2-cyclohexen-1-one (1f) also gave trifluoromethyl allylic alcohols (3f) in 92% yield. The intermediates (2a-f) and products (3a-f) are liquids and were characterized by IR, H-1, (19)f and C-13 NMR, MS, and high-resolution mass spectroscopy (HRMS).
• Trifluoromethylated Vinylic and Aromatic Compounds from α-(Trifluoro­methyl)allyl Alcohols
  作者：Bernard R. Langlois、Sylvie Radix-Large、Stéphanie Kucharski

  DOI：10.1055/s-2004-815928

  日期：——

  α-(Trifluoromethyl)allylalcohols, easily available from α,β-unsaturated carbonyl compounds, are readily converted into γ-(trifluoromethyl)allyl thioethers, benzyl ethers, trifluoroacetates, and azides. A phenyl substituent at the γ-position to the hydroxyl function enhances their reactivity and the ease of S N 2' or S N 1' substitutions, whereas a phenyl ring at the u-position allows the BF 3 -mediated

  α-(三氟甲基)烯丙醇很容易从 α,β-不饱和羰基化合物中获得，很容易转化为 γ-(三氟甲基)烯丙基硫醚、苄基醚、三氟乙酸酯和叠氮化物。羟基官能团的 γ 位上的苯基取代基增强了它们的反应性和 SN 2' 或 SN 1' 取代的容易程度，而 u 位上的苯环允许 BF 3 介导的 (三氟甲基) 茚的合成。4-烷基-4-甲氧基-1-(三氟甲基)环六-2,5-二烯醇，很容易从4-烷基苯酚中获得，很容易转化为带有亲核取代基(MeO，Cl)的4-烷基(三氟甲基)苯。环或苄基位置。