(Z)-1-methyl-4-(styrylsulfinyl)benzene | 41103-85-9

• 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: (Z)-1-methyl-4-(styrylsulfinyl)benzene
• 英文别名: (Z)-2-phenylvinyl p-tolyl sulfoxide；1-(p-tolylsulfinyl)-2-phenylethene；(+/-)-p-tolyl-cis-styryl sulfoxide；(+/-)-p-Tolyl-cis-styryl-sulfoxyd；1-methyl-4-[(Z)-2-phenylethenyl]sulfinylbenzene
• CAS: 41103-85-9；42970-39-8；56246-14-1；63268-44-0；71883-94-8；137693-72-2
• 化学式: C₁₅H₁₄OS
• 分子量: 242.342
• InChiKey: NZYCZBAOSXWZJS-QXMHVHEDSA-N

物化性质

• 熔点：
  82 °C
• 沸点：
  447.2±34.0 °C(predicted)
• 密度：
  1.19±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  17
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.07
• 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：

  (Z)-1-methyl-4-(styrylsulfinyl)benzene 在 氘代乙腈 、 tetramethylammonium tetrafluoroborate 作用下， 生成 C₁₅H₁₃⁽²⁾HOS
  参考文献：
  名称：

  A specific and regioselective electrocatalytic monodeuteriation of α,β-Unsaturated sulfoxides

  摘要：

  Unexpectedly the cathodic activation of a,a-ethylenic sulfoxides in deuteriated polar solvents permitted quantitative conversion into monodeuteriated analogs on condition that electrolyses were stopped after a catalytic amount of electricity has passed through the electrolysis cell.

  DOI：

  10.1016/0040-4039(95)01803-p
• 作为产物：
  描述：

  甲基对甲苯亚砜 在 正丁基锂 、 苯基锂 作用下， 以 乙醚 为溶剂， 反应 2.58h， 生成 (Z)-1-methyl-4-(styrylsulfinyl)benzene
  参考文献：
  名称：

  Stereoselective Synthesis of Racemic and Optically Active E-Vinyl and E-Dienyl Sulfoxides via Wittig Reaction of α-Sulfinyl Phosphonium Ylides

  摘要：

  A series of ol-sulfinyl phosphonium ylides have been obtained in the reaction of phosphonium mono- and diylides with sulfinic acid esters. The use of(-)-(S)-menthyl-p-toluenesulfinate in this reaction afforded the corresponding (S)-((p-tolylsulfinyl)methyl)triphenylphosphonium ylide. The Wittig reaction of these ylides with saturated and unsaturated aldehydes resulted in the formation of racemic and optically active (+)-(R)-vinyl and dienyl sulfoxides with the E-geometry. The synthesis of (+)-(R)-((p-tolylsulfinyl)methyl)triphenyl iodide as a precursor of the optically active ylide has also been described.

  DOI：

  10.1021/jo981100e

文献信息

• Metal-free, one-pot highly selective synthesis of (E)-vinyl sulfones and sulfoxides via addition–oxidation of thiols with alkynes
  作者：Qicai Xue、Zhijie Mao、Yan Shi、Haibin Mao、Yixiang Cheng、Chengjian Zhu

  DOI：10.1016/j.tetlet.2012.01.135

  日期：2012.4

  We have developed a highly selective one-pot method for the synthesis of (E)-vinyl sulfones and sulfoxides from thiols with terminal alkynes. The sulfones and sulfoxides could be obtained with excellent selectivity in good isolated yields. It is simple, efficient and environmentally benign, and metal-free. The mechanism for the formation of the (E)-vinyl sulfones was also proposed.

  我们已经开发了一种高度选择性的一锅法，用于从具有末端炔烃的硫醇合成（E）-乙烯基砜和亚砜。可以以良好的选择性和良好的分离收率获得砜和亚砜。它简单，高效且对环境无害，并且不含金属。还提出了形成（E）-乙烯基砜的机理。
• Synthesis of Vinyl Sulfoxides Using Sulfinyl Chlorides and Olefins
  作者：Xiancai Ding、Jianming Wen、Jianqiang Wang、Jun Yu、Jing-Hua Li

  DOI：10.3184/174751915x14304098020793

  日期：2015.5

  synthesis of vinyl sulfoxides, using sulfinyl chlorides and olefins as starting materials and DBU as an HCl scavenger, has been developed. Vinyl sulfoxides were obtained from the ZnCl2 catalysed addition of sulfinyl chlorides to olefins followed by the elimination with DBU. However, the direct reaction of sulfinyl chlorides with olefins in the presence of DBU, usually leads to generation of vinyl sulfones

  已经开发了一种合成乙烯基亚砜的通用方法，使用亚磺酰氯和烯烃作为起始原料，DBU 作为 HCl 清除剂。乙烯基亚砜是通过 ZnCl2 催化将亚磺酰氯加成到烯烃中，然后用 DBU 消除而获得的。然而，在 DBU 存在下，亚磺酰氯与烯烃的直接反应通常会导致生成乙烯基砜。由 DBU 介导的亚磺酰基歧化产生的磺酰基自由基与烯烃发生加成消除反应，得到乙烯基砜。
• (Diphenoxyphosphoryl)methyl <i>p</i>-tolyl sulfoxide: A new reagent for <i>Z</i>-selective synthesis of racemic and optically active vinyl sulfoxides
  作者：Wanda H. Midura、Ashraf M. Mohamed Ewas、Marian Mikołajczyk

  DOI：10.1080/10426507.2015.1114489

  日期：2016.3.3

  GRAPHICAL ABSTRACT ABSTRACT Racemic and optically active (+)-(S)-(diphenoxyphosphoryl)methyl p-tolyl sulfoxide were prepared and used as Horner olefination reagents. Their reaction with aromatic and aliphatic aldehydes afforded the corresponding racemic and enantiomeric α,β-unsaturated sulfoxides with moderate to high Z-selectivity. The E/Z ratio was found to be dependent on the structure of aldehyde

  图形摘要摘要制备了外消旋的和旋光的(+)-(S)-(二苯氧基磷酰基)甲基对甲苯基亚砜并用作Horner烯化试剂。它们与芳香族和脂肪族醛反应得到相应的外消旋和对映异构 α,β-不饱和亚砜，具有中等至高的 Z 选择性。发现 E/Z 比取决于醛的结构、碱的性质、反应条件和 18-crown-6 的添加。
• New carbon–carbon bond formation by the Pummerer-type reaction of vinylic sulphoxides with allylmagnesium bromide
  作者：Chuzo Iwata、Naoyoshi Maezaki、Toshiki Kurumada、Hidenori Fukuyama、Kenji Sugiyama、Takeshi Imanishi

  DOI：10.1039/c39910001408

  日期：——

  Vinylic sulphoxides underwent Pummerer-type reactions with allylmagnesium bromide to give diallylated sulphides together with monoallylated vinylic sulphides.

  乙烯基硫醚与烯丙基溴化镁发生普默尔型反应，生成二烯丙基硫化物和单烯丙基乙烯基硫化物。
• The Properties of Unsaturated Sulfur Compounds. I. Alpha Beta Unsaturated Sulfones
  作者：E. P. Kohler、H. Potter

  DOI：10.1021/ja01310a045

  日期：1935.7