1-(benzylsulfanyl)-3-(trifluoromethyl)benzene | 2251-27-6

• 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-(benzylsulfanyl)-3-(trifluoromethyl)benzene
• 英文别名: Benzyl 3-(trifluoromethyl)phenyl sulfide；1-benzylsulfanyl-3-(trifluoromethyl)benzene
• CAS: 2251-27-6
• 化学式: C₁₄H₁₁F₃S
• 分子量: 268.303
• InChiKey: IUEHPGHMQFDGPK-UHFFFAOYSA-N

物化性质

• 沸点：
  92-100 °C(Press: 0.2 Torr)
• 密度：
  1.26±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.8
• 重原子数：
  18
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.14
• 拓扑面积：
  25.3
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  1-(benzylsulfanyl)-3-(trifluoromethyl)benzene 在 1,3-二氯-5,5-二甲基海因 、 溶剂黄146 作用下， 以 二氯甲烷 、 水 为溶剂， 以90%的产率得到3-三氟甲基苯磺酰氯
  参考文献：
  名称：

  一种简单且高效的氧化氯化方案，用于制备芳磺酰氯

  摘要：

  发现2,4-二氯-5,5-二甲基乙内酰脲（DCDMH）是一种温和而有效的试剂，可通过氧化氯化以高至极好的收率将硫化合物直接氧化转化为相应的芳烃磺酰氯。该方法适用于多种类型的硫底物（硫醇，二硫化物和苄基硫化物）。整个过程简单，实用，并且可以方便地获得各种芳基或杂芳基磺酰氯。温和的反应条件和广泛的底物范围使该方法对现有的芳基或杂芳基磺酰氯合成方法具有吸引力和互补性。

  DOI：

  10.1016/j.tetlet.2009.11.047
• 作为产物：
  描述：

  3-碘三氟甲苯 、 苄硫醇 在 三乙烯二胺 、 copper(l) iodide 、 potassium carbonate 作用下， 以 乙二醇二甲醚 为溶剂， 反应 12.0h， 以99%的产率得到1-(benzylsulfanyl)-3-(trifluoromethyl)benzene
  参考文献：
  名称：

  A general and inexpensive protocol for the Cu-catalyzed C–S cross-coupling reaction between aryl halides and thiols

  摘要：

  A cost effective and easily available CuI/DABCO catalytic system has been developed for C-S cross-coupling reaction. This method is extremely useful for the thioetherification of aryl and heteroaryl halides providing excellent yields and good chemoselectivity. (C) 2015 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2015.10.014

文献信息

• <i>meta</i> C–H Arylation of Electron-Rich Arenes: Reversing the Conventional Site Selectivity
  作者：Luo-Yan Liu、Jennifer X. Qiao、Kap-Sun Yeung、William R. Ewing、Jin-Quan Yu

  DOI：10.1021/jacs.9b07887

  日期：2019.9.18

  report the first catalytic system that effectively performs meta C-H arylation of a variety of alkoxy aromatics including 2,3-dihydrobenzofuran and chromane with exclusive meta site-selectivity, thus reversing the conventional site selectivity governed by native electronic effects. The identification of an effective ligand and modified norbornene (NBE-CO2Me), as well as taking advantage of the statistics

  在不使用导向基团的情况下控制 CH 活化的位点选择性仍然是一个重大挑战。虽然由相互排斥的吡啶型配体调节的 Pd(II) 催化剂已被证明有利于芳烃相对富电子的碳中心，但逆转选择性以有利于相对缺电子位置的钯化作用是不可能的。在这里，我们报告了第一个催化系统，该系统有效地对包括 2,3-二氢苯并呋喃和色烷在内的各种烷氧基芳烃进行间位 CH 芳基化，具有独特的间位选择性，从而逆转了由天然电子效应控制的传统位点选择性。有效配体和改性降冰片烯 (NBE-CO2Me) 的鉴定，
• A Facile One-Pot Synthesis of Alkyl Aryl Sulfides from Aryl Bromides
  作者：Jungyeob Ham、Inho Yang、Heonjoong Kang

  DOI：10.1021/jo049758h

  日期：2004.4.1

  one-pot synthetic method for the formation of alkyl aryl sulfides from various alkyl halides and lithium aryl thiolates that are prepared in situ by direct halogen−lithium exchange is reported. In particular, the method overcomes many of the problems encountered in previous reports; it is very quick, catalyst-free, and does not involve use of unstable aryl thiols.

  报道了一种方便的一锅合成方法，该方法由各种烷基卤和芳基硫醇锂通过直接卤素-锂交换原位制备形成烷基芳基硫醚。尤其是，该方法克服了先前报告中遇到的许多问题。它非常快速，无催化剂，并且不涉及使用不稳定的芳基硫醇。
• Gold-catalyzed C–S bond formation from thiols
  作者：Mickaël Jean、Jacques Renault、Pierre van de Weghe、Naoki Asao

  DOI：10.1016/j.tetlet.2009.11.025

  日期：2010.1

  ortho-Alkynylbenzoic acid alkyl esters act as alkylating agents of thiol derivatives with PPh3AuCl in combination with AgOTf in 1,2-dichloroethane at 80 °C. The corresponding sulfide compounds are obtained in good to excellent yields.

  邻烷基炔基苯甲酸烷基酯在80°C下与1,2,2-二氯乙烷中的AgOTf一起与PPh 3 AuCl一起作为硫醇衍生物的烷基化剂。以良好至优异的产率获得相应的硫化物。
• Exploration of the mechanism and scope of the CuI/DABCO catalysed C S coupling reaction
  作者：Anns Maria Thomas、D.R. Sherin、Sujatha Asha、T.K. Manojkumar、Gopinathan Anilkumar

  DOI：10.1016/j.poly.2019.114269

  日期：2020.1

  A cost effective and easily available CuI/DABCO catalytic system has been developed for the C-S cross-coupling reaction. This method is extremely useful for the thioetherification of aryl and heteroaryl halides, providing excellent yields and good chemoselectivity. We have also explored the mechanism of the reaction using DFT studies. (C) 2019 Elsevier Ltd. All rights reserved.
• PROCESS FOR ALKYL ARYL SULFIDE DERIVATIVES AND NEW SULFIDE COMPOUNDS
  申请人：Kang Heonjoong

  公开号：US20090264660A1

  公开（公告）日：2009-10-22

  An alkyl aryl sulfide of Chemical Formula (III) is prepared by substituting an aryl halogen compound of Chemical Formula (I) with an alkyl lithium organometallic reagent. The sulfide is subsequently reacted with a compound of Chemical Formula (II). Alternatively an aryl halogen compound of Chemical Formula (I) is reacted with Grignard reagent to protect the hydrogen-donating substituent, and then reacted with an alkyl lithium organometallic reagent, and subsequently with sulfur and a compound of Chemical Formula (II). An alkyl aryl sulfide of Chemical Formula (III) is prepared via a one-step reaction without separation or purification of an intermediate compound from various aryl halogen compounds.