2,2'-disulfanediylbis[1-(4-chlorophenyl)ethanone] | 5409-94-9

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2,2'-disulfanediylbis[1-(4-chlorophenyl)ethanone]
• 英文别名: bis[2-(4-chlorophenyl)-2-oxoethyl] disulfide；2,2'-dithiobis[1-(4-chlorophenyl)ethanone]；bis(4-chlorophenacyl) disulfide；Bis-(p-chlor-phenacyl)-disulfid；1-(4-chlorophenyl)-2-[[2-(4-chlorophenyl)-2-oxoethyl]disulfanyl]ethanone
• CAS: 5409-94-9
• 化学式: C₁₆H₁₂Cl₂O₂S₂
• 分子量: 371.308
• InChiKey: HWLHHXIRZITARP-UHFFFAOYSA-N

物化性质

• 熔点：
  123-124 °C
• 沸点：
  536.9±45.0 °C(Predicted)
• 密度：
  1.399±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5
• 重原子数：
  22
• 可旋转键数：
  7
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  84.7
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2,2'-disulfanediylbis[1-(4-chlorophenyl)ethanone] 在 一水合肼 作用下， 以 溶剂黄146 为溶剂， 反应 1.67h， 以64%的产率得到(4Z,6Z)-4,7-Bis-(4-chloro-phenyl)-3,8-dihydro-[1,2,5,6]dithiadiazocine
  参考文献：
  名称：

  An Eight-Membered N,N,S,S-Heterocyclic Compound: 4,7-Bis(4-chlorophenyl)-3,8-dihydro-1,2,5,6-dithiadiazocine

  摘要：

  The eight-membered ring in the title compound, C16H12Cl2N2S2, adopts a non-planar conformation as expected, and the least-squares planes of the 4-substituted aromatic ring form a dihedral angle of 83.3(2)degrees as a result of steric constraints. The molecular dimensions are of general interest for comparison with structural data of analogous compounds.

  DOI：

  10.1107/s0108270197002588
• 作为产物：
  描述：

  Sodium;1-chloro-4-(2-sulfonatosulfanylacetyl)benzene 在 碘 作用下， 反应 1.0h， 以63%的产率得到2,2'-disulfanediylbis[1-(4-chlorophenyl)ethanone]
  参考文献：
  名称：

  An Eight-Membered N,N,S,S-Heterocyclic Compound: 4,7-Bis(4-chlorophenyl)-3,8-dihydro-1,2,5,6-dithiadiazocine

  摘要：

  The eight-membered ring in the title compound, C16H12Cl2N2S2, adopts a non-planar conformation as expected, and the least-squares planes of the 4-substituted aromatic ring form a dihedral angle of 83.3(2)degrees as a result of steric constraints. The molecular dimensions are of general interest for comparison with structural data of analogous compounds.

  DOI：

  10.1107/s0108270197002588

文献信息

• Synthesis of imidazolyl dithiocarbamates and their reactions with phenacyl bromides
  作者：O. S. El’tsov、V. S. Mokrushin、M. V. Smirnova、M. Z. Shafikov

  DOI：10.1007/s11172-011-0138-3

  日期：2011.5

  The reactions of ethyl (5-carbamoyl-3H-imidazol-4-yl)dithiocarbamate with phenacyl bromides afford the S-alkylation products as a mixture of E/Z-isomers, which undergo cyclization to 5-(2-oxo-4-arylthiazol-3-yl)-1H-imidazole-4-carboxamides under the action of a base.

  (5-氨基甲酰基-3H-咪唑-4-基)二硫代氨基甲酸乙酯与苯甲酰溴反应得到S-烷基化产物，为E/Z-异构体的混合物，其环化为5-(2-oxo-4-芳基噻唑-3-基)-1H-咪唑-4-甲酰胺在碱作用下。
• One-step synthesis of N-acetylcysteine and glutathione derivatives using the Ugi reaction
  作者：Alexander G. Zhdanko、Anton V. Gulevich、Valentine G. Nenajdenko

  DOI：10.1016/j.tet.2009.04.030

  日期：2009.6

  Cys–Gly, glutathione, and homoglutathione derivatives were synthesized by the Ugi four-component reaction using various benzylthio aldehydes and ketones as carbonyl building blocks. The scope and limitations of the method were investigated. Formation of imidazoline by-products in the Ugi reaction was discussed. 2,2,2-Trifluoroethanol was shown to be a superior reaction media than methanol in some reactions

  通过Ugi四组分反应，使用各种苄硫基醛和酮作为羰基结构单元，可以合成得到完全保护的天然和非天然N-乙酰半胱氨酸，二肽Cys-Gly，谷胱甘肽和高谷胱甘肽衍生物。研究了该方法的范围和局限性。讨论了在Ugi反应中咪唑啉副产物的形成。在某些反应中，显示2,2,2-三氟乙醇是一种比甲醇更好的反应介质。同样，当异氰基乙酸的更高反应性时，异氰基乙酸的4-甲基-2,6,7-三氧杂双环[2.2.2]辛基衍生物（OBO-酯）被证明比异氰基乙酸乙酯更适合用作肽合成前体。需要异氰酸酯。
• A green protocol for the synthesis of conformationally rigid sulfur linked bisquinolines by double Friedlander reaction in water
  作者：Nidhin Paul、Shanmugam Muthusubramanian、Nattamai Bhuvanesh

  DOI：10.1039/c1nj20539k

  日期：——

  bis(2-aryl-4-arylquinolin-3-yl)sulfanes and 1,2-bis(2-aryl-4-arylquinolin-3-yl)disulfanes were synthesised in good to excellent yields by double Friedlander reaction between 2-[(2-oxo-2-arylethyl)sulfanyl]-1-aryl-1-ethanones/2-[(2-oxo-2-arylethyl)disulfanyl]-1-aryl-1-ethanones and 2-aminobenzophenone with p-toluenesulfonic acid in water medium. An interesting restricted rotation of aryl rings has been noticed in b

  通过两次Friedlander反应，以良好的收率合成了一系列的双（2-芳基-4-芳基喹啉-3-基）硫烷和1,2-双（2-芳基-4-芳基喹啉-3-基）二硫烷。 2-[（（2-氧代-2-芳基乙基）硫烷基] -1-芳基-1-乙炔/ 2 / [[（2-氧代-2-芳基乙基）二硫烷基] -1-芳基-1-乙酮和 2-氨基二苯甲酮 和 对甲苯磺酸 在 水中等的。如NMR和晶体数据所示，在双（2-芳基-4-芳基喹啉-3-基）硫烷中注意到了芳基环的一个有趣的受限制的旋转。
• Mn(III)-based reactions of alkenes and alkynes with thiols. An approach toward substituted 2,3-dihydro-1,4-oxathiins and simple route to (E)-vinyl sulfides
  作者：Van-Ha Nguyen、Hiroshi Nishino、Shougo Kajikawa、Kazu Kurosawa

  DOI：10.1016/s0040-4020(98)00707-8

  日期：1998.9

  reaction with thioglycolic acid gave 1,4-oxathiolan-2-one 7. While thiyl radicals easily formed by manganese(III) oxidation with ethanethiol or benzenethiol reacted with alkynes to give preferentially (E)-vinyl sulfides 10 in quantitative yields.

  考察了在1,1-二芳烃与α-巯基酮反应中使用乙酸锰（III）的第一个实例。用乙酸锰（III）在乙酸中处理乙烯和α-巯基酮的混合物，得到中等收率的环加成产物以及取代的产物。该反应可能涉及碳正离子的形成和随后的环化，以得到取代的2,3-二氢-1,4-氧杂环丁烷3。与巯基乙酸的类似反应得到1，4-氧杂硫杂环戊烷-2-酮7。尽管通过锰（III）与乙硫醇或苯硫醇的氧化而容易形成的噻吩基与炔烃反应，以定量收率优先得到（E）-乙烯基硫化物10。
• Gas–solid chlorination of 4-phenylthiazole-2(1H)-thione
  作者：Veerapaneni Nalini、Gautam R. Desiraju

  DOI：10.1039/c39870001046

  日期：——

  The title compound (1) is converted into an unusual chlorophenacyl disulphide (2) through a crystal structure controlled chlorination–oxidation reaction.

  通过晶体结构控制的氯化-氧化反应，标题化合物（1）转化为不寻常的氯代苯甲酰二硫化物（2）。