(E)-1-phenyl-2,2-dimethylpropane-1-thione S-oxide | 78132-53-3

• 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: (E)-1-phenyl-2,2-dimethylpropane-1-thione S-oxide
• 英文别名: (Z)-1-phenyl-2,2-dimethylpropane-1-thione S-oxide；thiopivalophenone S-oxide；(2,2-Dimethyl-1-sulfinylpropyl)benzene
• CAS: 78132-53-3；87974-06-9；87974-07-0
• 化学式: C₁₁H₁₄OS
• 分子量: 194.298
• InChiKey: XUVJNLVVPZIFLM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  13
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.36
• 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：

  (E)-1-phenyl-2,2-dimethylpropane-1-thione S-oxide 在 劳森试剂 作用下， 以 二氯甲烷 为溶剂， 反应 0.08h， 生成 3-tert-butyl-3-phenyldithiirane
  参考文献：
  名称：

  Deoxygenation of Dithiirane 1-Oxides with Lawesson's Reagent Leading to the Corresponding Dithiiranes

  摘要：

  3,3-Disubstituted dithiirane 1-oxides were efficiently reduced with Lawesson's reagent (LR) to give the corresponding dithiiranes. X-ray diffraction analysis of 3,3di(1-adamantyl)dithiirane is reported. Reaction of S-34- labeled 3,3-di(1-adamantyl)dithiirane 1-oxide with LR produced the corresponding dithiirane in which the S-34 atoms were retained quantitatively.

  DOI：

  10.1021/jo026367z
• 作为产物：
  描述：

  2,2-二甲基-1-苯基丙烷-1-硫酮 在 二甲基二环氧乙烷 、 sulfur 作用下， 以 二氯甲烷 为溶剂， 反应 149.0h， 生成 (E)-1-phenyl-2,2-dimethylpropane-1-thione S-oxide
  参考文献：
  名称：

  通过 X 射线晶体学和 DFT 计算对 6-t-Butyl-6-phenylpentathane 一氧化物进行结构解析

  摘要：

  6-t-Butyl-6-phenylpentathiane 用三氟过乙酸 (CF3CO3H) 或二甲基二环氧乙烷 (DMD) 在 -20 °C 下氧化。用 CF3CO3H 氧化生成主要产物为戊四烷 3-氧化物，而 DMD 氧化生成 1- 和 3-氧化物。1-和3-氧化物的结构最终通过X-射线晶体学分析确定。NMR 化学位移的 DFT 计算是在 B3LYP/6-31G* 水平上使用 GIAO 方法对戊烷的椅子和扭曲形式和一氧化物的 16 种异构体进行的。计算出的化学位移经证实与戊烷和分离的 1- 和 3- 氧化物的实验数据实际一致。

  DOI：

  10.1246/bcsj.75.319

文献信息

• An S-oxide of 6-tert-butyl-6-phenylpentathiane. Structure in the crystalline state and in solution and thermal decomposition
  作者：Akihiko Ishii、Hideaki Oshida、Juzo Nakayama

  DOI：10.1016/s0040-4039(01)00383-5

  日期：2001.4

  Oxidation of 6-tert-butyl-6-phenylpentathiane with trifluoroperacetic acid gave the pentathiane 3-oxide mainly as the monooxide. The 3-oxide takes a twist conformation both in the crystalline state and in solution. Thermal decomposition of the 3-oxide in the presence of 2,3-dimethyl-1,3-butadiene yielded both S2O- and S2-transferred products.

  用三氟过氧乙酸氧化6-叔丁基-6-苯基戊烷得到的戊烷3-氧化物主要为一氧化物。3-氧化物在晶体状态和溶液中均具有扭曲构象。在2，3-二甲基-1，3-丁二烯存在下3-氧化物的热分解产生了S 2 O-和S 2转移的产物。
• Mechanism of oxidation of α,β-unsaturated thiones by singlet oxygen
  作者：V.Pushkara Rao、V. Ramamurthy

  DOI：10.1016/s0040-4020(01)96589-5

  日期：1985.1

  of α,β-unsaturated thiones yields the corresponding ketones as the only product. Studies carried out on three systems, namely thioketones, α,β-unsaturated thiones and thioketenes, have revealed that there exists a similarity in their mechanism of oxidation. It has been suggested that the thiocarbonyl chromophore is the site of attack by singlet oxygen in α,β-unsaturated thiones and that the adjacent

  α，β-不饱和硫酮的光氧化产生相应的酮作为唯一产物。对硫酮，α，β-不饱和硫酮和硫烯酮这三种体系进行的研究表明，它们的氧化机理存在相似之处。已经提出，硫代羰基发色团是α，β-不饱和硫酮中单线态氧的攻击位点，并且在这些条件下，相邻的CC双键是惰性的。α，β-不饱和硫酮氧化过程中缺少硫，归因于两性离子/双自由基中间体上的电子因子。尽管α，β-不饱和酮的反应性很差，但是α，β-不饱和的硫酮对单线态氧的反应性很高。
• 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。
• Photochemical oxidation of thio ketones: steric and electronic aspects
  作者：N. Ramnath、V. Ramesh、V. Ramamurthy

  DOI：10.1021/jo00150a015

  日期：1983.1
• Oxidation of <i>cis</i>- and <i>trans</i>-3,5-Di-<i>tert</i>-butyl-3,5-diphenyl-1,2,4-trithiolanes:  Isolation and Properties of the 1-Oxides and the 1,2-Dioxides
  作者：Hideaki Oshida、Akihiko Ishii、Juzo Nakayama

  DOI：10.1021/jo0354591

  日期：2004.3.1

  Oxidation of trans-3,5-di-tert-butyl-3,5-diphenyl-1,2,4-trithiolane with dimethyldioxirane (DMD) or m-chloroperbenzoic acid MCPBA) gave two stereoisomeric (1S*,3S*,5S*)- and (1R*,3S*,5S*)1-oxides (16 and 17, respectively). Oxidation of 16 with DMD gave the (1S*,2R*,3S*,5S*)-1,2-dioxide (18) and the 1,1-dioxide 19, and that of 17 yielded the (1R*,2R*,3S*,5S*)-1,2-dioxide (20) mainly along with IS and 19. The structures of the 1,2-dioxides 18 and 20 were determined by X-ray crystallography. 1,2-Dioxides 18 and 20 isomerized to each other in solution, and the equilibrium constant K (20/18) is 19 in CDCl3 at 295 K. The kinetic study suggested a biradical mechanism for the isomerization. Isomerization of 16 and 17 to cis-3,5-di-tert-butyl-1,2,4-trithiolane I-oxides by treatment with Me3O+BF4- is also described.