1-chloro-4-(phenyl(tosyl)methyl)benzene | 102078-57-9

• 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-chloro-4-(phenyl(tosyl)methyl)benzene
• 英文别名: p-chlorophenyl(phenyl)methyl p-tolyl sulfone；(4-chloro-benzhydryl)-p-tolyl sulfone；(4-Chlor-benzhydryl)-p-tolyl-sulfon；1-[(4-Chlorophenyl)-phenylmethyl]sulfonyl-4-methylbenzene
• CAS: 102078-57-9
• 化学式: C₂₀H₁₇ClO₂S
• 分子量: 356.873
• InChiKey: QTEQLBNAPAVPGP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.3
• 重原子数：
  24
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.1
• 拓扑面积：
  42.5
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  4-溴苯酚 、 1-chloro-4-(phenyl(tosyl)methyl)benzene 在 scandium tris(trifluoromethanesulfonate) 作用下， 以 1,2-二氯乙烷 为溶剂， 反应 12.0h， 以87%的产率得到[2-(4-bromo-1-hydroxyphenyl)](4-chlorophenyl)phenylmethane
  参考文献：
  名称：

  Arylative Desulfonation of Diarylmethyl Phenyl Sulfone with Arenes Catalyzed by Scandium Triflate

  摘要：

  A scandium-triflate-catalyzed arylative desulfonation of diarylmethyl phenyl sulfones with arenes and heteroarenes was established. A variety of both sulfone and arene substrates were reacted to afford symmetric and nonsymmetric triarylmethanes in good yields. Further transformations of the resulting triarylmethanes and application to the concise synthesis of a bactericidal agent analogue were also demonstrated.

  DOI：

  10.1021/acs.orglett.6b00744
• 作为产物：
  描述：

  4-氯二苯甲醇 、 对甲基苯磺酰甲基异腈 在 三氟化硼乙醚 作用下， 以 乙腈 为溶剂， 以80%的产率得到1-chloro-4-(phenyl(tosyl)methyl)benzene
  参考文献：
  名称：

  BF3·Et2O 催化的醇与 TosMIC 反应的底物和温度控制发散：轻松获得亚磺酸盐和砜

  摘要：

  摘要 从醇和对甲苯磺酰甲基异氰化物 (TosMIC) 中，通过形成 C-O 和 C-S 键实现了 BF3·Et2O 催化的亚磺酸酯和砜的有效发散合成。各种醇在当前条件下在室温下与 TosMIC 平稳反应，仅提供亚磺酸酯。通过调节反应温度，在反应介质中提供高度稳定的碳正离子的醇提供了作为唯一产物的砜。本研究旨在了解双齿亚磺酸盐离子的区域选择性并阐明亚磺酸盐/砜支架的解释。图形概要

  DOI：

  10.1080/00397911.2017.1321128

文献信息

• Direct sulfonylation of Baylis–Hillman alcohols and diarylmethanols with TosMIC in ionic liquid-[Hmim]HSO4: an unexpected reaction
  作者：Garima、Vishnu P. Srivastava、Lal Dhar S. Yadav

  DOI：10.1016/j.tetlet.2011.06.096

  日期：2011.9

  A Bronsted acidic ionic liquid-[Hmim]HSO4 promoted unexpected reaction of Baylis-Hillman alcohols and diarylmethanols with p-toluenesulfonylmethyl isocyanide (TosMIC) affording the corresponding sulfone derivatives instead of N-tosylmethyl amides is reported. After isolation of the product, the ionic liquid [Hmim]HSO4 was easily recycled for further use. (C) 2011 Elsevier Ltd. All rights reserved.
• Palladium-catalyzed benzylic direct arylation of benzyl sulfones with aryl halides
  作者：Takashi Niwa、Hideki Yorimitsu、Koichiro Oshima

  DOI：10.1016/j.tet.2009.01.030

  日期：2009.3

  An effective palladium catalyst system for the direct arylation of benzyl sulfones with aryl halides has been developed. The catalytic reaction provides a facile route to diarylmethyl sulfones. The products can be transformed further via desulfonylative functionalization mediated by aluminum compounds. (C) 2009 Elsevier Ltd. All rights reserved.
• Wragg et al., Journal of the Chemical Society, 1958, p. 3603
  作者：Wragg et al.

  DOI：——

  日期：——
• Arylative Desulfonation of Diarylmethyl Phenyl Sulfone with Arenes Catalyzed by Scandium Triflate
  作者：Masakazu Nambo、Zachary T. Ariki、Daniel Canseco-Gonzalez、D. Dawson Beattie、Cathleen M. Crudden

  DOI：10.1021/acs.orglett.6b00744

  日期：2016.5.20

  A scandium-triflate-catalyzed arylative desulfonation of diarylmethyl phenyl sulfones with arenes and heteroarenes was established. A variety of both sulfone and arene substrates were reacted to afford symmetric and nonsymmetric triarylmethanes in good yields. Further transformations of the resulting triarylmethanes and application to the concise synthesis of a bactericidal agent analogue were also demonstrated.
• Substrate- and temperature-controlled divergence in reactions of alcohols with TosMIC catalyzed by BF₃ · Et₂O: Facile access to sulfinates and sulfones
  作者：Naresh Pogaku、Palakodety Radha Krishna、Y. Lakshmi Prapurna

  DOI：10.1080/00397911.2017.1321128

  日期：2017.7.3

  ABSTRACT An efficient BF3 · Et2O-catalyzed divergent synthesis of sulfinate esters and sulfones through C–O and C–S bond formation has been achieved from alcohols and p-toluenesulfonylmethyl isocyanide (TosMIC). Various alcohols reacted smoothly with TosMIC under the present conditions at room temperature providing sulfinate esters exclusively. By tuning the reaction temperature, the alcohols that

  摘要 从醇和对甲苯磺酰甲基异氰化物 (TosMIC) 中，通过形成 C-O 和 C-S 键实现了 BF3·Et2O 催化的亚磺酸酯和砜的有效发散合成。各种醇在当前条件下在室温下与 TosMIC 平稳反应，仅提供亚磺酸酯。通过调节反应温度，在反应介质中提供高度稳定的碳正离子的醇提供了作为唯一产物的砜。本研究旨在了解双齿亚磺酸盐离子的区域选择性并阐明亚磺酸盐/砜支架的解释。图形概要