1,2-bis((4-chlorophenyl)thio)ethane | 5409-87-0

• 分子结构分类: 有机化合物 - 有机硫化合物 - 硫醚类
• 英文名称: 1,2-bis((4-chlorophenyl)thio)ethane
• 英文别名: 1,2-bis-(4-chloro-phenylsulfanyl)-ethane；1,2-Bis-(4-chlor-phenylmercapto)-aethan；1,2-bis(4-chlorophenylthio)ethane；1-Chloro-4-[2-(4-chlorophenyl)sulfanylethylsulfanyl]benzene
• CAS: 5409-87-0
• 化学式: C₁₄H₁₂Cl₂S₂
• 分子量: 315.287
• InChiKey: QCCIQLSVFMEUDX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.9
• 重原子数：
  18
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.14
• 拓扑面积：
  50.6
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  1,2-bis((4-chlorophenyl)thio)ethane 在 双氧水 、 溶剂黄146 作用下， 反应 1.0h， 生成 1,2-bis-(4-chloro-benzenesulfonyl)-ethane
  参考文献：
  名称：

  Baliah, V.; Aparajithan, K., Journal of the Indian Chemical Society, 1992, vol. 69, # 5, p. 255 - 259

  摘要：

  DOI：
• 作为产物：
  描述：

  1-氯-4-[(2-氯乙基)硫代]苯 在 sodium cyanide 作用下， 以 二甲基亚砜 为溶剂， 反应 5.0h， 以99%的产率得到1,2-bis((4-chlorophenyl)thio)ethane
  参考文献：
  名称：

  Salbeck, Gerhard, Phosphorus and Sulfur and the Related Elements, 1982, vol. 13, p. 165 - 168

  摘要：

  DOI：

文献信息

• A highly efficient heterogeneous rhodium(I)-catalyzed C-S coupling reaction of thiols with polychloroalkanes or alkyl halides under mild conditions
  作者：Jianhui Xia、Ruiya Yao、Mingzhong Cai

  DOI：10.1002/aoc.3273

  日期：2015.4

  Heterogeneous C–S coupling reaction of thiols with polychloroalkanes or alkyl halides was achieved at 30 or 80 °C in the presence of 5 mol% of an MCM‐41‐immobilized bidentate phosphine rhodium complex (MCM‐41‐2P‐RhCl(PPh3)) and triethylamine, yielding a variety of formaldehyde dithioacetals, ethylenedithioethers and unsymmetric thioethers in good to excellent yields. This heterogeneous rhodium catalyst

  在30或80°C下，在5 mol％的MCM‐41固定的双齿膦膦铑配合物（MCM‐41‐2‐2P‐RhCl（PPh 3））和三乙胺，可产生各种甲醛二硫缩醛，乙二硫醚和不对称硫醚，收率高至优异。这种多相铑催化剂可通过简单过滤反应溶液而容易地回收和再循环，并至少连续进行了10次试验，而活性没有明显损失。版权所有©2015 John Wiley＆Sons，Ltd.
• SOME ARALKYL AND ARYL ALKYL SULPHIDES AND DISULPHIDES
  作者：Marshall Kulka、F. G. Van Stryk

  DOI：10.1139/v57-073

  日期：1957.6.1

  Sixty sulphides and disulphides have been prepared from mercaptans and alkyl and alkylene halides for testing as insecticides.

  已经从硫醇和烷基卤化物和亚烷基卤化物制备了 60 种硫化物和二硫化物，用于作为杀虫剂进行测试。
• A Bulky Disulfoxide Ligand for Pd-Catalyzed Oxidative Allylic C–H Amination with 2,2,2-Trichloroethyl Tosyl Carbamate
  作者：You-Gui Li、Li Li、Ming-Yue Yang、Gang He、Eric Assen B. Kantchev

  DOI：10.1021/acs.joc.6b03089

  日期：2017.5.5

  Challenging substrates and conditions in homogeneous catalysis pose stringent demands on the ligands used. A novel, bulky, 1-adamantyl-substituted disulfoxide ligand designed after a systematic evaluation of the electronic and steric properties of disulfoxide substituents permits the allylic oxidative C–N coupling reaction to proceed at lower catalyst loading while requiring a smaller excess of reagents

  在均相催化中具有挑战性的底物和条件对所用的配体提出了严格的要求。在对二亚砜取代基的电子和空间特性进行系统评估之后，设计了一种新颖的，大体积的1-金刚烷基取代的二亚砜配体，使烯丙基氧化C-N偶联反应可以在较低的催化剂负载量下进行，而所需的试剂用量则更少。另外，当使用TsNHCOOCH 2 CCl 3（一种允许在酸性和碱性条件下将产物脱保护的新型试剂）时，该配体可提高收率。
• The toxicity of organic sulphides to the eggs and larvae of the glasshouse red spider mite. I.—SS′-disubstituted alkane-αω-dithiols
  作者：R. F. Brookes、J. E. Cranham、W. A. W. Cummings、D. Greenwood、B. S. Jackson、H. A. Stevenson

  DOI：10.1002/jsfa.2740080106

  日期：1957.1

  A laboratory test method for assessing the activity of chemicals against the eggs and young mites of the glasshouse red spider (Tetranychus telarius L.) is described. The results given by a series of SS′-disubstituted alkane-αω-dithiols using this test method are tabulated and discussed.

  描述了一种实验室测试方法，用于评估化学品对温室红蜘蛛（Tetranychus telarius L.）的卵和幼螨的活性。使用该测试方法由一系列 SS'-二取代烷烃-αω-二硫醇给出的结果列表和讨论。
• REACTIONS OF 2,3,5,6-TETRAKIS(β-HYDROXYETHYLMERCAPTO)-1,4-HYDROQUINONE AND RELATED COMPOUNDS
  作者：Marshall Kulka

  DOI：10.1139/v62-191

  日期：1962.7.1

  The treatment of chloranil (I) with alkali and 2-mercaptoethanol resulted not only in replacement of the chlorine atoms but also in reduction to form 2,3,5,6-tetrakis(β-hydroxyethylmercapto)-1,4-hydroquinone (II). The conditions for the preparation of 2,3,5,6-tetrakis(β-chloroethylmercapto)-1,4-hydroquinone (III) from II differed from those required for the preparation of a lower-melting compound (IV) from II by such a narrow margin that exact control of temperature and concentration were necessary in order to avoid erratic behavior in the preparation. The structure of the lower-melting compound has been established as 2,3-dihydro-5,7,8-tris(β-chloroethylmercapto)-6-hydroxy-1,4-benzoxathiin (IV) by analyses and cyclization reactions. The treatment of 2,3-dichloro-1,4-naphthoquinone (VIII) with 2-mercaptoethanol yielded 2,3-bis(β-hydroxyethylmercapto)-1,4-naphthoquinone (IX) and not the quinol as was the case with chloranil. The quinone (IX) could not be converted to 2,3-bis(β-chloroethylmercapto)-1,4-naphthoquinone by treatment with hydrogen chloride because under these conditions only 1,4-oxathio-5,10-anthraquinone (X) was formed. A mechanism for the formation of X which involves intramolecular addition, elimination, and cyclization is described.

  氯醌（I）与碱和2-巯基乙醇的处理不仅导致氯原子的取代，还导致还原形成2,3,5,6-四(β-羟乙基巯基)-1,4-氢醌（II）。从II制备2,3,5,6-四(β-氯乙基巯基)-1,4-氢醌（III）的条件与从II制备较低熔点化合物（IV）的条件有所不同，需要精确控制温度和浓度，以避免制备过程中的不稳定行为。通过分析和环化反应，已确定较低熔点化合物的结构为2,3-二氢-5,7,8-三(β-氯乙基巯基)-6-羟基-1,4-苯并噻嗪（IV）。将2,3-二氯-1,4-萘醌（VIII）与2-巯基乙醇处理得到2,3-双(β-羟乙基巯基)-1,4-萘醌（IX），而不像氯醌那样生成醌醇。醌（IX）无法通过氯化氢处理转化为2,3-双(β-氯乙基巯基)-1,4-萘醌，因为在这些条件下只形成了1,4-氧硫-5,10-蒽醌（X）。描述了涉及分子内加成、消除和环化的X形成机制。