4,4'-dichlorothiobenzophenone S-oxide | 33240-29-8

• 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: 4,4'-dichlorothiobenzophenone S-oxide
• 英文别名: bis-(4-chloro-phenyl)-methanethione S-oxide；bis-(4-chloro-phenyl)-sulfinyl-methane；4,4'-dichloro-thiobenzophenone S-oxide；Methanethione, bis(4-chlorophenyl)-, S-oxide；1-chloro-4-[(4-chlorophenyl)-sulfinylmethyl]benzene
• CAS: 33240-29-8
• 化学式: C₁₃H₈Cl₂OS
• 分子量: 283.178
• InChiKey: PRHLZYHQMYVTCB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.5
• 重原子数：
  17
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  18.1
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  4,4'-dichlorothiobenzophenone S-oxide 以 氘代氯仿 为溶剂， 生成 4,4'-二氯二苯甲酮
  参考文献：
  名称：

  Direct Thioepoxidation of Strained Cyclic Alkenes by the Photolytic Sulfur-Atom Transfer from Thiocarbonyl S-Oxides (Sulfines)

  摘要：

  DOI：

  10.1021/jo971133e
• 作为产物：
  描述：

  4,4'-二氯二苯甲酮 在 盐酸 、 oxygen 、 硫化氢 作用下， 以 乙醇 、 乙腈 为溶剂， 反应 24.0h， 生成 4,4'-dichlorothiobenzophenone S-oxide
  参考文献：
  名称：

  Photochemical oxidation of thio ketones: steric and electronic aspects

  摘要：

  DOI：

  10.1021/jo00150a015

文献信息

• Mechanistic investigations into the photochemical oxidation of thioketones
  作者：N. Ramnath、V. Ramesh、V. Ramamurthy

  DOI：10.1039/c39810000112

  日期：——

  Singlet-oxygen reaction with dialkyl, aryl alkyl, and diaryl thioketones is found to give the corresponding sulphines and ketones in proportions depending on the nature of the thioketone.

  发现与二烷基，芳基烷基和二芳基硫代酮的单线态氧反应可根据硫代酮的性质按比例产生相应的硫磺和酮。
• Carbonyl sulfides as possible intermediates in the photolysis of oxathiiranes
  作者：Lars Carlsen、James P. Snyder、Arne Holm、Erik Pedersen

  DOI：10.1016/s0040-4020(01)92060-5

  日期：1981.1

  Diphenyl oxathiirane, formed by irradiation of thiobenzophenone S-oxide at 77 K, is photochemically converted into a blue, thermally unstable compound which decomposes at ca 100–110 K (λmax 550 nm, (ϵ ca 11,000). Lack of change in magnetic susceptibility during the light induced conversion of sulfine to ketone via the oxathiirane and the subsequent blue intermediate implies the absence of triplet and

  二苯氧杂环乙烷是由硫代二苯甲酮S-氧化物在77 K的辐射下形成的，被光化学转化为一种蓝色的热不稳定化合物，其在大约100–110 K时分解（λ最大550 nm，（ϵ大约11,000））。到酮经由oxathiirane和随后的蓝色中间锍化的光致转换期间敏感性意味着不存在三重态和双自由基单峰瞬变的。未知硫化羰的功能，R 2 COS，从而出现作为制造的有力候选可见吸收。
• Study of reactions leading to sulfine formation. 5. Methoxide-catalyzed decomposition of diarylmethyl(arylsulfonyl)methyl sulfoxides: a sulfine-forming elimination on the E1cBrev/(E1cB)irrev borderline
  作者：John L. Kice、Lidia Kupczyk-Subotkowska

  DOI：10.1021/jo00004a017

  日期：1991.2

  In 7:3 CH3OH-DMSO (v/v) in the presence of methoxide ion, diarylmethyl (arylsulfonyl)methyl sulfoxides (Ar2CHS(O)CH2SO2Ar') 4, undergo elimination remarkably easily to afford the diarylsulfine and the aryl methyl sulfone (eq 4). Comparison of the rate of cleavage of 4 (k(elim)) and the rate of disappearance of the H-1 NMR signal (k(CHSO)) for the Ar2CHS(O) proton in CD3OD-DMSO shows that the mechanism for the elimination is on the (E1cB)rev/(E1cB)irrev borderline, (k(CHSO)/k(elim)) ranging from 1.2 to 5.2, depending on the nature of the Ar and Ar' groups in 4. Slight changes in structure can shift the mechanism from (E1cB)rev to (E1cB)irrev as a result of their effect on the partitioning of the alpha-sulfinyl carbanion intermediate (Ar2CBARS(O)CH2SO2Ar') 5, between cleavage to diarylsulfine plus ArSO2CH2- (step k(ii), eq 8) and protonation to regenerate 4 (step k(-i). Structural changes that make Ar'SO2CH2 a better leaving group increase k(ii)/k(-i)[MeOD] and shift the mechanism toward (E1cB)irrev as does also an increase in the percentage of DMSO in the solvent. Structural changes in Ar that enhance the stability of 5 decrease k(ii)/k(-i)[MeOD] and shift the mechanism toward (E1cB)rev. It is also shown that for 4 in general k(ii) appears larger than would be expected for a leaving group of the basicity of Ar'SO2CH2-. Repulsion between the dipoles of the S(O) and SO2 groups in 5 is thought to be responsible.
• Elimination reactions of alkanesulfinyl derivatives: mechanism and reactivity in base-induced sulfine formation from methyl diarylmethanesulfinates
  作者：John L. Kice、Juliusz J. Rudzinski

  DOI：10.1021/ja00242a027

  日期：1987.4
• A Convenient Preparation of Sulfines (R₂CSO) from Thioketones
  作者：Ruili Huang、James H. Espenson

  DOI：10.1021/jo990967p

  日期：1999.9.1