trimethyl{[(2E)-3-phenyl-1,1-bis(trifluoromethyl)prop-2-enyl]oxy}silane | 247912-50-1

• 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: trimethyl{[(2E)-3-phenyl-1,1-bis(trifluoromethyl)prop-2-enyl]oxy}silane
• 英文别名: (E)-trimethyl{[1,1,1-trifluoro-4-phenyl-2-(trifluoromethyl)but-3-en-2-yl]oxy}silane；trimethyl-[(E)-1,1,1-trifluoro-4-phenyl-2-(trifluoromethyl)but-3-en-2-yl]oxysilane
• CAS: 247912-50-1
• 化学式: C₁₄H₁₆F₆OSi
• 分子量: 342.356
• InChiKey: UQARFGKOJPWNCX-MDZDMXLPSA-N

物化性质

• 沸点：
  49-50 °C(Press: 0.02 Torr)
• 密度：
  1.189±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.41
• 重原子数：
  22
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  9.2
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  trimethyl{[(2E)-3-phenyl-1,1-bis(trifluoromethyl)prop-2-enyl]oxy}silane 在 盐酸 作用下， 以 四氢呋喃 为溶剂， 反应 3.0h， 以95%的产率得到(E)-1,1,1-trifluoro-4-phenyl-2-(trifluoromethyl)but-3-en-2-ol
  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
• 作为产物：
  描述：

  肉桂酸 在 4-二甲氨基吡啶 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 、 cesium fluoride 作用下， 以 四氢呋喃 、 1,4-二氧六环 为溶剂， 反应 6.0h， 生成 trimethyl{[(2E)-3-phenyl-1,1-bis(trifluoromethyl)prop-2-enyl]oxy}silane
  参考文献：
  名称：

  氟阴离子引发的苯基芳族羧酸盐与（三氟甲基）三甲基硅烷的双三氟甲基化

  摘要：

  苯基芳香族羧酸盐与（三氟甲基）三甲基硅烷（Me 3 SiCF 3）的氟阴离子引发的反应是形成O-甲硅烷基保护的2-芳基-1,1,1,1,3,3,3-六氟异丙醇报告。在苯基羧酸酯的三氟甲基化过程中产生的酚盐阴离子也会活化Me 3 SiCF 3，从而允许使用催化量的氟化物阴离子源。在反应中可以容忍可用于进一步修饰的各种官能团。

  DOI：

  10.1039/d0cc04826g

文献信息

• Convenient syntheses of 1,1,1,3,3,3-hexafluoro-2-organyl-propan-2-ols and the corresponding trimethylsilyl ethers
  作者：L.A. Babadzhanova、N.V. Kirij、Yu.L. Yagupolskii、W. Tyrra、D. Naumann

  DOI：10.1016/j.tet.2004.12.023

  日期：2005.2

  A new convenient synthetic procedure to obtain various 1, 1, 1,3,3,3-hexafluoro-2-organyl-propan-2-ols and the corresponding trimethylsilyl ethers has been worked out starting from anhydrides or activated esters of carboxylic acids and trimethyl(trifluoromethyl)silane in the presence of tetramethylammonium fluoride. Conditions for the selective formation of 1, 1, 1,3,3,3-hexafluoro-2-organyl-propan-2-ols as well as the trimethylsilyl derivatives have been found. (C) 2004 Elsevier Ltd. All rights reserved.
• Fluoride anion-initiated bis-trifluoromethylation of phenyl aromatic carboxylates with (trifluoromethyl)trimethylsilane
  作者：Kenjiro Takahashi、Yusuke Ano、Naoto Chatani

  DOI：10.1039/d0cc04826g

  日期：——

  carboxylates with (trifluoromethyl)trimethylsilane (Me3SiCF3) that results in the formation of O-silyl-protected 2-aryl-1,1,1,3,3,3-hexafluoroisopropanols is reported. A phenoxide anion, generated during the trifluoromethylation of the phenyl carboxylate, also activates the Me3SiCF3, which permits a catalytic amount of the fluoride anion source to be used. Various functional groups, which can be used for further

  苯基芳香族羧酸盐与（三氟甲基）三甲基硅烷（Me 3 SiCF 3）的氟阴离子引发的反应是形成O-甲硅烷基保护的2-芳基-1,1,1,1,3,3,3-六氟异丙醇报告。在苯基羧酸酯的三氟甲基化过程中产生的酚盐阴离子也会活化Me 3 SiCF 3，从而允许使用催化量的氟化物阴离子源。在反应中可以容忍可用于进一步修饰的各种官能团。
• 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).