3,3,3-trifluoro-2-hydroxy-1-(4-methylphenyl)-propan-1-one | 118110-45-5

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 3,3,3-trifluoro-2-hydroxy-1-(4-methylphenyl)-propan-1-one
• 英文别名: 1-(4-Methylphenyl)-3,3,3-trifluoro-2-hydroxy-1-propanone；3,3,3-trifluoro-2-hydroxy-1-(4-methylphenyl)propan-1-one
• CAS: 118110-45-5
• 化学式: C₁₀H₉F₃O₂
• 分子量: 218.175
• InChiKey: BRHXOAAWENKUJT-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  15
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  37.3
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  2-ethoxy-1,1,1-trifluoro-3-(4-methylphenyl)-2,3-bistrimethylsiloxypropane 在 四丁基氟化铵 作用下， 以 四氢呋喃 为溶剂， 以65%的产率得到3,3,3-trifluoro-2-hydroxy-1-(4-methylphenyl)-propan-1-one
  参考文献：
  名称：

  通过苯甲醛的还原性三氟乙酰化和羰基的转位轻松合成芳族不对称含氟酰基

  摘要：

  在镁和氯代三甲基硅烷存在下，在N-甲基-2-吡咯烷酮中，苯甲醛与三氟乙酸乙酯之间的还原偶联反应以良好的收率得到了相应的偶联化合物的缩醛。偶联产物的产率在很大程度上取决于溶液中苯甲醛的浓度，为了获得高产率的偶联产物，必须避免形成频哪醇类化合物。随后使用四丁基氟化铵对乙缩醛进行脱甲硅烷基化反应，在羰基通过酮-烯醇互变异构体转位后，很容易得到酰基化合物。

  DOI：

  10.1016/j.tet.2014.02.016

文献信息

• A Convenient Synthesis of 5-Aryl-6-trifluoromethyl-3,6-dihydro-2<i>H</i>-1,3,4-oxadiazines. A Silica Gel Catalyzed Novel Cyclization Reaction
  作者：Yasuhiro Kamitori、Masaru Hojo、Ryöich Masuda、Toshihiko Fujitani、Seiji Ohara、Tetsuya Yokoyama

  DOI：10.1055/s-1988-27513

  日期：——

  Arenecarbaldehyde dimethylhydrazones were successfully acylated by trifluoroacetic anhydride to afford trifluoroacetylated hydrazones 2. Several 5-Aryl-6-trifluoromethyl-3,6-dihydro-2H-1,3,4-oxadiazines 3 were synthesized in good yields by novel cyclization of 2, thus obtained, using silica gel as an effective catalyst. Hydrolytic ring cleavage of 3 afforded α-hydroxyketones 5 bearing the trifluoromethyl group in high yields.

  三氟乙酸酐成功地将烯丙基醛二甲基腙酰化，得到三氟乙酰腙 2。通过硅胶作为有效催化剂，对所得的 2 进行新颖的环化反应，合成了几种 5-芳基-6-三氟甲基-3,6-二氢-2H-1,3,4-恶二嗪 3，收率良好。3 的水解环裂解以高收率提供了带有三氟甲基的 α-羟基酮 5。
• Diketo Compounds with (Trifluoromethyl)trimethylsilane:  Double Nucleophilic Trifluoromethylation Reactions
  作者：Rajendra P. Singh、Jeffry M. Leitch、Brendan Twamley、Jean'ne M. Shreeve

  DOI：10.1021/jo0057304

  日期：2001.2.1

  Reactions of various diketo compounds with (trifluoromethyl)trimethylsilane (Me3SiCF3) in the presence of catalytic amounts of cesium fluoride have been studied. gamma -Ketoesters, CH3COCH2CH2CH2R (R = Et, Bu), were reacted with 2 equiv of Me3SiCF3 at room temperature to give CH3C(OH)(CF3)CH2CH2COCF3 in good yield after hydrolysis. alpha -Diketones, R1COCOR2 (R-1 = R-2 = Ph; R-1 = Ph, R-2 = Me; R-1 = R-2 = Me; R-1 = Me, R-2 = Et), when reacted with Me3SiCF3, formed 1:1 or 1:2 addition products depending on the reaction conditions and stoichiometry used. Reactions of diones CH3COXCOCH3 (X = -CH2CH2-, -C6H4C6H4-, -CH2-) with Me3SiCF3 also led to the formation of the mono- or diaddition products depending on reaction conditions. With various kinds of substituted arylglyoxals, 2 equiv of Me3SiCF3 produced monoaddition products in 70-75% yield and diaddition products in 5-10% yield. One of the monoalcohols and two of the diols have been characterized by single-crystal X-ray analysis, and the presence of inter- and intramolecular hydrogen bonding has been confirmed.
• Facile synthesis of aromatic unsymmetrical fluorine-containing acyloins through the reductive trifluoroacetylation of benzaldehyde and transposition of the carbonyl group
  作者：Hirofumi Maekawa、Masashi Kudo、Yutaro Nishiyama、Kazuyuki Shimizu、Mitsuhiro Abe

  DOI：10.1016/j.tet.2014.02.016

  日期：2014.3

  The reductive coupling reaction between benzaldehyde and ethyl trifluoroacetate in the presence of magnesium and chlorotrimethylsilane in N-methyl-2-pyrrolidinone gave the acetal of the corresponding coupling compound in good yields. The yield of the coupling product largely depended on the benzaldehyde concentration in the solution and it was essential to avoid the formation of pinacol type compounds

  在镁和氯代三甲基硅烷存在下，在N-甲基-2-吡咯烷酮中，苯甲醛与三氟乙酸乙酯之间的还原偶联反应以良好的收率得到了相应的偶联化合物的缩醛。偶联产物的产率在很大程度上取决于溶液中苯甲醛的浓度，为了获得高产率的偶联产物，必须避免形成频哪醇类化合物。随后使用四丁基氟化铵对乙缩醛进行脱甲硅烷基化反应，在羰基通过酮-烯醇互变异构体转位后，很容易得到酰基化合物。