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

• A simple and highly effective oxidative chlorination protocol for the preparation of arenesulfonyl chlorides
  作者：Yu-Ming Pu、Alan Christesen、Yi-Yin Ku

  DOI：10.1016/j.tetlet.2009.11.047

  日期：2010.1

  suitable for many types of sulfur substrates (thiols, disulfides, and benzylic sulfides). The overall process is simple, practical, and it provides convenient access to a variety of aryl or heteroarylsulfonyl chlorides. The mild reaction conditions and the broad substrate scope render this method attractive and complementary to existing syntheses of aryl or heteroarylsulfonyl chlorides.

  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。
• 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。
• A general and inexpensive protocol for the Cu-catalyzed C–S cross-coupling reaction between aryl halides and thiols
  作者：Anns Maria Thomas、Sujatha Asha、K.S. Sindhu、Gopinathan Anilkumar

  DOI：10.1016/j.tetlet.2015.10.014

  日期：2015.11

  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.
• 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.