[1-(4-chloro-phenyl)-2,2,2-trifluoro-1-methyl-ethoxy]-trimethylsilane

• 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: [1-(4-chloro-phenyl)-2,2,2-trifluoro-1-methyl-ethoxy]-trimethylsilane
• 英文别名: [2-(4-Chlorophenyl)-1,1,1-trifluoropropan-2-yl]oxy-trimethylsilane
• 化学式: C₁₂H₁₆ClF₃OSi
• 分子量: 296.792
• InChiKey: KBRIEUDATXXQBU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.97
• 重原子数：
  18
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  9.2
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  [1-(4-chloro-phenyl)-2,2,2-trifluoro-1-methyl-ethoxy]-trimethylsilane 在 四磷十氧化物 、 硫酸 作用下， 生成 1-氯-4-(3,3,3-三氟丙-1-烯-2-基)苯
  参考文献：
  名称：

  One-pot synthesis of α-trifluoromethylstyrenes from aryl ketones and the Ruppert–Prakash reagent

  摘要：

  DOI：

  10.1016/j.mencom.2021.09.030
• 作为产物：
  描述：

  对氯苯乙酮 、 (三氟甲基)三甲基硅烷 在 tris(2,4,6-trimethoxyphenyl)-phosphine 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 0.5h， 以85%的产率得到[1-(4-chloro-phenyl)-2,2,2-trifluoro-1-methyl-ethoxy]-trimethylsilane
  参考文献：
  名称：

  TTMPP催化的三氟甲基硅烷对羰基化合物和亚胺的三氟甲基化

  摘要：

  高碱性膦，三（2,4,6-三甲氧基苯基）膦（TTMPP）使用三氟甲基三甲基硅烷催化三氟甲基化，以羰基化合物和亚胺的高至高收率得到相应的三氟甲基化产物。

  DOI：

  10.1016/j.tetlet.2008.05.053

文献信息

• TBD-Catalyzed Trifluoromethylation of Carbonyl Compounds with (Trifluoromethyl)trimethylsilane
  作者：S. Matsukawa、S. Takahashi、H. Takahashi

  DOI：10.1080/00397911.2011.644381

  日期：2013.6.3

  Abstract Trifluoromethylation of carbonyl compounds using (trifluoromethyl) trimethylsilane catalyzed by 1,5,7-triazabicyclo[4,4,0]dec-5-ene (TBD) afforded the corresponding α-trifluoromethyl alcohols in good to excellent yields under mild reaction conditions. Supplemental materials are available for this article. Go to the publisher's online edition of Synthetic Communications® to view the free supplemental

  摘要 在 1,5,7-三氮杂双环 [4,4,0]dec-5-烯 (TBD) 催化下，使用（三氟甲基）三甲基硅烷对羰基化合物进行三氟甲基化反应，在温和的反应条件下以良好至极好的产率得到相应的 α-三氟甲醇。 . 补充材料可用于本文。转至出版商的 Synthetic Communications® 在线版以查看免费的补充文件。图形概要
• TTMPP-catalyzed trifluoromethylation of carbonyl compounds and imines with trifluoromethylsilane
  作者：Satoru Matsukawa、Marina Saijo

  DOI：10.1016/j.tetlet.2008.05.053

  日期：2008.7

  A highly basic phosphine, tris(2,4,6-trimethoxyphenyl)phosphine (TTMPP), catalyzes trifluoromethylation using trifluoromethyltrimethylsilane to give the corresponding trifluoromethylated products in good to high yields, with both carbonyl compounds and imines.

  高碱性膦，三（2,4,6-三甲氧基苯基）膦（TTMPP）使用三氟甲基三甲基硅烷催化三氟甲基化，以羰基化合物和亚胺的高至高收率得到相应的三氟甲基化产物。
• Cs2CO3-Initiated Trifluoro-Methylation of Chalcones and Ketones for Practical Synthesis of Trifluoromethylated Tertiary Silyl Ethers
  作者：Cheng Dong、Xing-Feng Bai、Ji-Yuan Lv、Yu-Ming Cui、Jian Cao、Zhan-Jiang Zheng、Li-Wen Xu

  DOI：10.3390/molecules22050769

  日期：——

  It was found that 1,2-trifluoromethylation reactions of ketones, enones, and aldehydes were easily accomplished using the Prakash reagent in the presence of catalytic amounts of cesium carbonate, which represents an experimentally convenient, atom-economic process for this anionic trifluoromethylation of non-enolisable aldehydes and ketones.

  发现酮、烯酮和醛的 1,2-三氟甲基化反应在催化量的碳酸铯存在下使用 Prakash 试剂很容易完成，这代表了非离子三氟甲基化的实验方便、原子经济的过程。 -可烯醇化的醛和酮。
• Facile Synthesis of TMS-Protected Trifluoromethylated Alcohols Using Trifluoromethyltrimethylsilane (TMSCF₃) and Various Nucleophilic Catalysts in DMF
  作者：G. K. Surya Prakash、Chiradeep Panja、Habiba Vaghoo、Vijayalakshmi Surampudi、Roman Kultyshev、Mihirbaran Mandal、Golam Rasul、Thomas Mathew、George A. Olah

  DOI：10.1021/jo060835d

  日期：2006.9.1

  Organofluorine compounds are becoming increasingly important in different fields, such as material science, agro chemistry, and the pharmaceutical industry. Nucleophilic trifluoromethylation is one of the widely used methods to incorporate a trifluoromethyl moiety into organic molecules. We have carried out extensive studies to develop varieties of easily accessible nucleophilic catalysts to promote such reactions. TMS-protected trifluoromethylated alcohols were prepared from both aldehydes and ketones in excellent yields using catalytic amount of amine N-oxide. Carbonate and phosphate salts also showed efficient catalytic activity toward this reaction. These reactions were highly solvent dependent, and DMF was found to be the most suitable one among the various solvents studied. All these reactions proceeded under very mild conditions, giving clean products and avoiding the use of any fluoride initiators or expensive catalysts, and extremely water-free conditions. The mechanism for the reaction is discussed in detail. DFT calculations were performed on the possible reaction intermediates using the Gaussian 03 program at B3LYP/6-311+G* level to support the proposed mechanism.
• One-pot synthesis of α-trifluoromethylstyrenes from aryl ketones and the Ruppert–Prakash reagent
  作者：Vitalij V. Levin、Alexander D. Dilman

  DOI：10.1016/j.mencom.2021.09.030

  日期：2021.9