1-phenylethenyl(phenyl)sulfoxide | 49833-32-1

• 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: 1-phenylethenyl(phenyl)sulfoxide
• 英文别名: 1-phenyl-1-(phenylsulfinyl)-ethene；[1-(phenylsulfinyl)vinyl]benzene；1-(Benzenesulfinyl)ethenylbenzene
• CAS: 49833-32-1
• 化学式: C₁₄H₁₂OS
• 分子量: 228.315
• InChiKey: BTHJYZWXASQPRN-UHFFFAOYSA-N

物化性质

• 沸点：
  444.5±24.0 °C(Predicted)
• 密度：
  1.20±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  16
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  36.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  1-phenylethenyl(phenyl)sulfoxide 在 碘代三甲硅烷 作用下， 以 氯仿 为溶剂， 反应 6.0h， 以70%的产率得到苯乙酮
  参考文献：
  名称：

  An investigation of the behaviour of α,β-unsaturated sulfoxides in the presence of trimethylsilyl iodide

  摘要：

  A mild, efficient and seemingly general method for converting alpha,beta-unsaturated sulfoxides into carbonyl compounds by means of trimethylsilyl iodide (TMSI) is described. Experiments on different substrates and trimethylsilyl halides lead to the conclusion that the oxidation state of the sulfur atom, on one hand, and halogen kind in TMSX on the other, assume a determining role in the progression of the reaction. The ease of experimental procedure, the possibility of H-1 NMR monitoring, and good yields of final products constitute advantages of the TMSI-promoted conversion of alpha,beta-unsaturated sulfoxides into carbonyl compounds. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(02)01365-0
• 作为产物：
  描述：

  α-phenylthiostyrene 在 sodium periodate 作用下， 生成 1-phenylethenyl(phenyl)sulfoxide
  参考文献：
  名称：

  Reactions of Vinyl Sulfoxides with Magnesium Amides. One-Pot Synthesis of Symmetrical and Unsymmetrical β-(Dialkylamino) Dithioacetals

  摘要：

  Vinyl sulfoxides (PhSOCR1=CHR2: R-1 = H, Me, or Ph; R-2 = H Or Me) were treated with (dialkylamino)magnesium reagents, generated in situ from the reaction of EtMgBr with secondary amines ((RRNH)-R-3-N-4: R-3 = Et, i-Pr, or Bn; R-4 = Me, Et, or i-Pr) in refluxing Et2O for 1 h, and stirring at room-temperature overnight gave the corresponding symmetrical beta-(dialkylamino) dithioacetals [(PhS)(2)(CRCHRNRR4)-C-1-N-2-R-3] in 24-84% yields. When the (diethylamino)magnesium reagent was treated with appropriate thiols (RSH; R = p-ClC6H4 or Bn) prior to the interaction with phenyl vinyl sulfoxide, the corresponding unsymmetrical beta-(diethylamino) dithioacetals [(PhS)(RS)CHCH2NEt2] were produced in 63-67% yields.

  DOI：

  10.1021/jo970741r

文献信息

• Stabilization of Organic Materials
  申请人：Gerster Michele

  公开号：US20080269382A1

  公开（公告）日：2008-10-30

  The invention describes a process for stabilizing an organic material against oxidative, thermal or light-induced degradation, which comprises incorporating therein or applying thereto at least a compound of the formula (I) wherein the general symbols are as defined in claim 1 . The compounds of the formula I are especially useful as processing stabilizers for synthetic polymers.

  该发明描述了一种用于稳定有机材料抵抗氧化、热降解或光诱导降解的过程，其中包括将化合物（I）至少混入其中或应用于其中，其中通式中的一般符号如权利要求1所定义。通式I的化合物特别适用作合成聚合物的加工稳定剂。
• Exploiting Substrate Diversity for Preparing Synthetically Valuable Sulfoxides via Asymmetric Hydrogenative Kinetic Resolution
  作者：Héctor Fernández-Pérez、Joan R. Lao、Arnald Grabulosa、Anton Vidal-Ferran

  DOI：10.1002/ejoc.202000592

  日期：2020.8.2

  The ability of a rhodium catalyst derived from phosphine‐phosphite ligands to hydrogenatively resolve a set of structurally diverse α,β‐unsaturated vinyl sulfoxides is reported. The practicality of the methodology was applied to the preparation of precursors of biologically active compounds.

  据报道，衍生自膦-亚磷酸酯配体的铑催化剂能够氢化分解一组结构多样的α，β-不饱和乙烯基亚砜。该方法的实用性被用于制备生物活性化合物的前体。
• Conjugate addition of alkyl groups to α,β-unsaturated sulfoxides via Michael addition of nitroparaffins and subsequent denitration with tributyltin hydride
  作者：Noboru Ono、Hideyoshi Miyake、Akio Kamimura、Nobuo Tsukui、Aritsune Kaji

  DOI：10.1016/s0040-4039(00)87505-x

  日期：1982.1

  Michael addition of nitroparaffins to α,β-unsaturated sulfoxides is well effected in the presence of DBU. The nitro group in the adduct is replaced by hydrogen with Bu3SnH without influence to the sulfinyl function. The overall reations provide an efficient method for the conjugate addition of alkyl groups to α,β-unsaturated sulfoxides.

  在DBU的存在下，将硝基链烷烃迈克尔加成到α，β-不饱和亚砜上是有效的。加合物中的硝基被Bu 3 SnH取代为氢，而不影响亚磺酰基的功能。整体反应为将烷基共轭加成到α，β-不饱和亚砜上提供了一种有效的方法。
• Contrasting pathways for the directed homogeneous hydrogenation of vinyl sulfoxides and vinyl sulfones
  作者：David Ando、Christopher Bevan、John M. Brown、David W. Price

  DOI：10.1039/c39920000592

  日期：——

  Rh-complex catalysed directed hydrogenation of (α-hydroxyalkyl)vinyl sulfones follows the same stereochemical course as the corresponding acrylates, via HO-coordination; hydrogenation of the related (α-hydroxyalkyl)vinyl sulfoxides is directed by S–O coordination, which overrides HO-participation and is shown to be general.

  Rh 络合物催化的（α-羟烷基）乙烯基砜的直接氢化反应遵循与相应丙烯酸酯相同的立体化学过程，通过 HO 配位；相关的（α-羟烷基）乙烯基亚砜的氢化是由S-O配位指导的，它优先于HO-参与，并且被证明是普遍的。
• Unexpected conversion of vinyl sulfoxides into carbonyl compounds by means of iodotrimethylsilane
  作者：Maria C Aversa、Anna Barattucci、Paola Bonaccorsi、Giuseppe Bruno、Placido Giannetto、Manuela Policicchio

  DOI：10.1016/s0040-4039(00)00612-2

  日期：2000.6

  The unexpected and previously unknown TMSI-promoted conversion of α,β-unsaturated sulfoxides into carbonyl compounds and disulfides is described. It occurs in good yields under mild conditions. The examples provided support the generality and efficiency of this procedure which acts as a good method for removing the sulfinyl group with the advantage of transforming the vinyl sulfoxides into carbonyl

  描述了出乎意料且以前未知的TMSI促进的α，β-不饱和亚砜转化为羰基化合物和二硫化物。在温和条件下产量高。所提供的实施例支持了该方法的一般性和效率，该方法是除去亚磺酰基的良好方法，具有将乙烯基亚砜转化为羰基化合物的优点。