2-(phenylsulfanyl)ethyl phenyl sulfone | 29290-71-9

• 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: 2-(phenylsulfanyl)ethyl phenyl sulfone
• 英文别名: phenyl 2-(phenylthio)ethyl sulfone；phenyl(2-(phenylsulfonyl)ethyl)sulfane；1-benzenesulfonyl-2-phenylsulfanyl-ethane；(2-phenylsulfanyl-ethanesulfonyl)-benzene；1-Benzolsulfonyl-2-phenylmercapto-aethan；Benzene, [[2-(phenylsulfonyl)ethyl]thio]-；2-(benzenesulfonyl)ethylsulfanylbenzene
• CAS: 29290-71-9
• 化学式: C₁₄H₁₄O₂S₂
• 分子量: 278.396
• InChiKey: HVRFBKAMRWDDMG-UHFFFAOYSA-N

物化性质

• 熔点：
  71-71.5 °C
• 沸点：
  469.6±37.0 °C(Predicted)
• 密度：
  1.28±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 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：
  67.8
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2-(phenylsulfanyl)ethyl phenyl sulfone 在 双氧水 、 溶剂黄146 作用下， 生成 1,2-联苯磺酰乙烷
  参考文献：
  名称：

  Benzothiophene Chemistry. VI. A Peroxide Effect in the Addition of Thiophenols to Benzothiophene 1-Dioxide

  摘要：

  DOI：

  10.1021/ja01643a009
• 作为产物：
  描述：

  在 甲醇 、 三苯基膦 作用下， 以85%的产率得到2-(phenylsulfanyl)ethyl phenyl sulfone
  参考文献：
  名称：

  Reactivity in Z-philic displacements in α-halogenosulfones

  摘要：

  β-取代的α-溴砜中的亲Z反应速率已被测定；对于取代-质子化反应，速率比 ρ*= 2.9，且接近2.4的同位素分馏因子表明过渡结构中存在广泛的碳-质子化。

  DOI：

  10.1039/c39930001609

文献信息

• Organocatalytic Asymmetric Synthesis of Sulfoxides from Sulfenic Acid Anions Mediated by a <i>Cinchona</i>-Derived Phase-Transfer Reagent
  作者：Fabien Gelat、Jayadevan Jayashankaran、Jean-François Lohier、Annie-Claude Gaumont、Stéphane Perrio

  DOI：10.1021/ol2010962

  日期：2011.6.17

  Preliminary results concerning a conceptually novel route to chiral sulfoxides based on the asymmetric alkylation of sulfenate salts with alkyl halides mediated by a chiral phase-transfer catalyst are described. As a representative example, o-anisyl methyl sulfoxide was produced in 96% yield and with an enantiomeric excess of 58% using commercial cinchonidinium derivative 2a.

  本文描述了有关手性亚砜在手性相转移催化剂介导的亚磺酸盐与烷基卤化物的不对称烷基化的基础上获得手性亚砜的新颖方法的初步结果。作为代表性的例子，ö -anisyl甲基亚砜，96％收率和58％对映体过量使用商业金鸡尼丁衍生物制备2A。
• Elimination and addition reactions. Part 33. Formation and behaviour of carbanions derived from sulphones and nitriles bearing β-′onium substituents
  作者：Kenneth N. Barlow、Donald R. Marshall、Charles J. M. Stirling

  DOI：10.1039/p29770001920

  日期：——

  Kinetics of elimination reactions of β-arylsulphonylethyl- and β-cyanoethyl-ammonium and -sulphonium salts have been measured in ethanolic triethylamine buffers. The reactions show buffer saturation kinetics; at low buffer base concentrations ionisation to form the intermediate carbanion is rate-determining, but at higher buffer base concentrations the intermediate carbanion is formed in a rapidly

  已经在乙醇三乙胺缓冲液中测量了β-芳基磺酰基乙基-和β-氰基乙基铵和-磺酸盐的消除反应的动力学。反应显示出缓冲液饱和动力学。在低缓冲碱浓度下，电离形成中间碳负离子是决定速率的，但是在较高缓冲碱浓度下，中间碳负离子是在快速建立的预平衡步骤中形成的，在恒定缓冲液下，观察到的速率常数不会随碱浓度的增加而变化。比率。
• One‐pot <scp>sulfa‐Michael</scp> addition reactions of disulfides using a pyridine‐borane complex under blue light irradiation
  作者：Changhee Park、Sunggi Lee

  DOI：10.1002/bkcs.12574

  日期：2022.7

  We report a one-pot sulfa-Michael addition reaction using a disulfide and a pyridine-borane complex under blue light irradiation. This novel synthetic approach has a broad substrate scope and a high functional group tolerance. Mechanistic studies suggest that sequential radical and ionic processes provide a practical solution for constructing carbon–sulfur bonds.

  我们报告了在蓝光照射下使用二硫化物和吡啶-硼烷复合物的单锅磺胺-迈克尔加成反应。这种新的合成方法具有广泛的底物范围和高官能团耐受性。机理研究表明，连续的自由基和离子过程为构建碳硫键提供了实用的解决方案。
• Selectivity Reversal during Thia-Michael Additions Using Tetrabutylammonium Hydroxide: Operationally Simple and Extremely High Turnover
  作者：Daniel Nicponski、Jennifer Marchi

  DOI：10.1055/s-0033-1341106

  日期：——

  The use of tetrabutylammonium hydroxide as a novel and exceedingly efficient thia-Michael addition catalyst is herein described. This extremely simple methodology allows for the conjugate addition of a wide variety of mercaptan nucleophiles, and functions remarkably well with a very wide range of both classical and non-classical Michael acceptors. Contradistinctive to current literature reports, the use of this catalyst more efficiently promotes the addition of more basic thiols. This methodology is especially attractive and operationally simple, as it generally proceeds with only 1 mol% catalytic loading and without excess reagent, and the produced products typically require no purification.
• Aryl vinyl sulfones as thiol protective group
  作者：Yoshiaki Kuroki、Robert Lett

  DOI：10.1016/s0040-4039(00)99838-1

  日期：1984.1