2-(trifluoromethyl)allyl 4-methylbenzenesulfonate | 693826-80-1

• 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: 2-(trifluoromethyl)allyl 4-methylbenzenesulfonate
• 英文别名: Toluene-4-sulfonic acid 2-trifluoromethylallyl ester；2-(trifluoromethyl)prop-2-enyl 4-methylbenzenesulfonate
• CAS: 693826-80-1
• 化学式: C₁₁H₁₁F₃O₃S
• 分子量: 280.268
• InChiKey: CNIFRGFGGHYSIV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  18
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  51.8
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  tert-butyl 2-(2-phenylacetyl)-2-(1-phenylallyl)hydrazine-1-carboxylate 、 2-(trifluoromethyl)allyl 4-methylbenzenesulfonate 在 sodium hydride 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 以76%的产率得到tert-butyl 2-(2-phenylacetyl)-2-(1-phenylallyl)-1-(2-(trifluoromethyl)allyl)hydrazine-1-carboxylate
  参考文献：
  名称：

  RCM 介导的氟化环肼合成

  摘要：

  使用氟化和三氟甲基化烯烃的闭环复分解 (RCM) 作为关键步骤，已经以简单的方式制备了一系列氟化环肼衍生物。

  DOI：

  10.1055/s-2008-1032043
• 作为产物：
  描述：

  toluene-4-sulfonic acid 2-trifluoromethylbicyclo[2.2.1]hept-5-ene-2-methyl ester 600.0 ℃ 、4.0 Pa 条件下， 以95%的产率得到2-(trifluoromethyl)allyl 4-methylbenzenesulfonate
  参考文献：
  名称：

  Fluorinated (hetero)cycles via ring-closing metathesis of fluoride- and trifluoromethyl-functionalized olefins

  摘要：

  Ring-closing metathesis(RCM) has been shown to be a viable tool to incorporate fluoride and trifluoromethyl substituents in (hetero)cyclic ring systems. 2-Fluoroacrylamides were cyclized to the corresponding lactams, and trifluoromethyl- substituted olefins were cyclized to yield trifluoromethylated cyclopentenes, pyrrolines and a dihydrofuran derivative. (C) 2003 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2003.11.093

文献信息

• THERAPEUTIC COMPOUNDS AND METHODS OF USE THEREOF
  申请人：GENENTECH, INC.

  公开号：US20180105504A1

  公开（公告）日：2018-04-19

  The invention provides a compound of formula I: or a pharmaceutically acceptable salt thereof, wherein the variables X, Y 1 -Y 5 , R 1 , R 2 , R 3 , R 4 , and Het have the meaning as described herein, and compositions containing such compounds and methods for using such compounds and compositions.

  本发明提供了一种式I化合物：或其药学上可接受的盐，其中变量X、Y1-Y5、R1、R2、R3、R4和Het的含义如本文所述，以及含有此类化合物的组合物和使用此类化合物及组合物的方法。
• An Improved Ring-Closing Metathesis Approach to Fluorinated and Trifluoromethylated Nitrogen Heterocycles
  作者：Valeria De Matteis、Olivier Dufay、Dennis C. J. Waalboer、Floris L. van Delft、Jörg Tiebes、Floris P. J. T. Rutjes

  DOI：10.1002/ejoc.200601119

  日期：2007.6

  The synthesis of fluoro- and trifluoromethyl-containing N-sulfonylated nitrogen heterocycles is described. A first crucial step is a Mitsunobu functionalization of intermediate sulfonamides using commercially available unsaturated alcohols, which gives efficient access to fluorinated ring-closing metathesis (RCM) precursors. Key step is an RCM reaction of these precursors leading to the corresponding

  描述了含氟和三氟甲基的 N-磺酰化氮杂环的合成。第一个关键步骤是使用市售不饱和醇对中间体磺酰胺进行 Mitsunobu 功能化，从而有效地获得氟化闭环复分解 (RCM) 前体。关键步骤是这些前体的 RCM 反应导致相应的含氟和三氟甲基的杂环结构单元。此外，相同磺酰胺中间体的氨基钯化提供了获得含三氟甲基的吡咯衍生物的途径。（© Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2007）
• Catalytic enantioselective intramolecular 1,3-dipolar cycloaddition of azomethine ylides with fluorinated dipolarophiles
  作者：Christian Cristóbal、Daniel Gaviña、Inés Alonso、María Ribagorda、Juan C. Carretero、Carlos del Pozo、Javier Adrio

  DOI：10.1039/d2cc02902b

  日期：——

  An enantioselective synthesis of polycyclic fluorinated pyrrolidines has been achieved by Cu-catalyzed intramolecular 1,3-dipolar cycloaddition of azomethine ylides with fluorinated dipolarophiles. The method displays a wide scope and afforded the desired cycloadducts in high yields with up to 99% ee. These results demonstrate that fluoroalkyl substituents are excellent activating groups in this transformation

  多环氟化吡咯烷的对映选择性合成是通过铜催化的偶氮亚甲基叶立德与氟化偶极体的分子内 1,3-偶极环加成反应实现的。该方法显示范围广，并以高达 99% 的 ee 高产率提供了所需的环加合物。这些结果表明，氟烷基取代基是这种转化中极好的活化基团。
• RCM-Mediated Synthesis of Trifluoromethyl-Containing Nitrogen Heterocycles
  作者：Valeria De Matteis、Floris L. van Delft、Harald Jakobi、Stephen Lindell、Jörg Tiebes、Floris P. J. T. Rutjes

  DOI：10.1021/jo060893z

  日期：2006.9.1

  A ring-closing metathesis mediated pathway to trifluoromethyl-containing piperidines is detailed. This involves the development of a synthetic route to a new (trifluoromethyl)allylating reagent via a Diels-Alder/retro-Diels-Alder strategy, its application in the synthesis of a series of trifluormethyl-substituted diolefin precursors for ring-closing metathesis, and eventually the successful cyclization of these precursor molecules into the corresponding functionalized piperidines.
• NEW ISOXAZOLYL ETHER DERIVATIVES AS GABA A ALPHA5 PAM
  申请人：Hoffmann-La Roche Inc.

  公开号：US20210094945A1

  公开（公告）日：2021-04-01

  The invention provides novel compounds having the general formula (I) or (II) wherein R 2 , R 3 , R 5 , R 99 , W, Y and Z are as described herein, compositions including the compounds and methods of using the compounds.