cyclopropyl phenyl sulfoxide | 50337-59-2

• 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: cyclopropyl phenyl sulfoxide
• 英文别名: (cyclopropylsulfinyl)benzene；phenyl cyclopropyl sulfoxide；Benzene, (cyclopropylsulfinyl)-；cyclopropylsulfinylbenzene
• CAS: 50337-59-2
• 化学式: C₉H₁₀OS
• 分子量: 166.244
• InChiKey: UCXWXPWJUXXCPX-UHFFFAOYSA-N

物化性质

• 沸点：
  319.2±11.0 °C(Predicted)
• 密度：
  1.26±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  11
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.33
• 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：

  cyclopropyl phenyl sulfoxide 在 N-氯代丁二酰亚胺 作用下， 以 四氯化碳 为溶剂， 生成 1-chlorocyclopropyl phenyl sulfoxide
  参考文献：
  名称：

  基于环亚丙基镁与α-磺酰基碳负离子反应的亚烷基环丙烷的合成新方法

  摘要：

  在低温下用异丙基氯化镁处理1-氯环丙基苯基亚砜，得到环亚丙基镁。发现产生的类胡萝卜素与α-磺酰基碳负离子锂的反应以中等至良好的产率提供了亚烷基环丙烷。该反应提供了一种新颖，前所未有，用途广泛的方法，可以在较短的时间内由烯烃合成几种亚烷基环丙烷。

  DOI：

  10.1016/j.tetlet.2003.10.162
• 作为产物：
  描述：

  苯硫酚 在 间氯过氧苯甲酸 、 sodium hydroxide 作用下， 以 乙醇 、 二氯甲烷 为溶剂， 反应 19.5h， 生成 cyclopropyl phenyl sulfoxide
  参考文献：
  名称：

  亚砜到亚磺胺的转化：使用修饰的Burgess型试剂

  摘要：

  AbstractSulfoxides can directly be converted into N‐cyanosulfilimines using a new Burgess‐type reagent. By applying this strategy with a related reagent variant, synthetically valuable NH‐sulfoximines have been prepared from sulfoxides via N‐protected sulfilimines. The practical three‐step reaction sequence is generally high yielding and applicable to a wide range of substrates. The sulfoxide‐to‐sulfilimine conversion can also be performed under solvent‐reduced conditions in a ball mill.magnified image

  DOI：

  10.1002/adsc.201300766

文献信息

• Polyoxomolybdate-Calix[4]arene Hybrid: A Catalyst for Sulfoxidation Reactions with Hydrogen Peroxide
  作者：Sara Meninno、Alessandro Parrella、Giovanna Brancatelli、Silvano Geremia、Carmine Gaeta、Carmen Talotta、Placido Neri、Alessandra Lattanzi

  DOI：10.1021/acs.orglett.5b02607

  日期：2015.10.16

  polyoxomolybdate–calix[4]arene hybrid 1 has been synthesized and applied as a heterogeneous catalyst in the sulfoxidation of thioethers to sulfoxides and to sulfones under strictly stoichiometric amounts of 30% H2O2 in CH3CN as the solvent. This study represents the first promising example of successful employment of calixarenes–polyoxometalate (POM) hybrid materials in the area of catalytic oxidations.

  合成了一种容易获得的聚氧钼酸盐-杯[4]芳烃杂化物1，并作为非均相催化剂在严格化学计量的CH 3 CN中以30％H 2 O 2为溶剂将硫醚硫氧化为亚砜和砜。这项研究代表了在催化氧化领域成功使用杯芳烃-多金属氧酸盐（POM）杂化材料的第一个有希望的例子。
• A highly efficient reusable homogeneous copper catalyst for the selective aerobic oxygenation sulfides to sulfoxides
  作者：Cheng Ren、Runxing Fang、Xiaochun Yu、Shun Wang

  DOI：10.1016/j.tetlet.2018.01.066

  日期：2018.3

  catalysis of oxidation of sulfides to sulfoxides using molecular oxygen as the oxidant. The reaction proceeds under mild conditions in the presence of a catalytic amount of TEMPO. Importantly, the catalysts could be conveniently recovered and reused. And this methodology was proved to be applicable for the transformation of various aromatic and aliphatic sulfides into the corresponding sulfoxides with high

  现成的铜对于使用分子氧作为氧化剂的硫化物氧化为亚砜的均相催化，显示出高效的活性和很高的选择性。反应在温和条件下在催化量的TEMPO存在下进行。重要的是，催化剂可以方便地回收和再利用。事实证明，该方法适用于以高转化率和高选择性将各种芳族和脂族硫化物转化为相应的亚砜。
• Photocatalytic Deoxygenation of Sulfoxides Using Visible Light: Mechanistic Investigations and Synthetic Applications
  作者：Aimee K. Clarke、Alison Parkin、Richard J. K. Taylor、William P. Unsworth、James A. Rossi-Ashton

  DOI：10.1021/acscatal.0c00690

  日期：2020.5.15

  The photocatalytic deoxygenation of sulfoxides to generate sulfides facilitated by either Ir[(dF(CF3)ppy)2(dtbbpy)]PF6 or fac-Ir(ppy)3 is reported. Mechanistic studies indicate that a radical chain mechanism operates, which proceeds via a phosphoranyl radical generated from a radical/polar crossover process. Initiation of the radical chain was found to proceed via two opposing photocatalytic quenching

  报道了通过Ir [（dF（CF 3）ppy）2（dtbbpy）] PF 6或fac -Ir（ppy）3促进的亚砜的光催化脱氧生成硫化物。机理研究表明，自由基链机理起作用，其通过由自由基/极性交叉过程产生的磷酰基自由基进行。发现自由基链的引发通过两种相反的光催化猝灭机理进行，从而提供互补的反应性。自由基脱氧过程的温和性质使得能够以通常的高分离收率还原多种官能化的亚砜，包括那些含有酸敏感基团的亚砜。
• Electrochemical Properties and Fluorination of Cyclopropane Derivatives Bearing Arylthio Groups
  作者：Sayaka Oyanagi、Hideki Ishii、Shinsuke Inagi、Toshio Fuchigami

  DOI：10.1149/1945-7111/abb83b

  日期：2020.1.12

  Electrochemical analyses of phenylthiocyclopropane derivatives and bis(arylthio)cyclopropanes were comparatively studied by cyclic voltammetric measurements. Based on the substituent effects on their oxidation potentials, a cyclopropane ring was confirmed to have a double bond system as reported. Anodic fluorination of phenylthiocyclopropanes resulted in the formation of sulfoxide and/or ring opening

  通过循环伏安法比较研究了苯硫基环丙烷衍生物和双（芳硫基）环丙烷的电化学分析。基于取代基对其氧化电势的影响，已证实环丙烷环具有双键系统。苯硫基环丙烷的阳极氟化导致形成亚砜和/或开环氟化产物，而1,1-双（芳硫基）环丙烷主要提供脱硫的单氟化环丙烷和亚砜以及开环氟化产物。这是环丙烷环的首次成功的电化学氟化。
• Nickel ferrite nanoparticles–hydrogen peroxide: a green catalyst-oxidant combination in chemoselective oxidation of thiols to disulfides and sulfides to sulfoxides
  作者：Aparna M. Kulkarni、Uday V. Desai、Kapil S. Pandit、Makarand A. Kulkarni、Prakash P. Wadgaonkar

  DOI：10.1039/c4ra04095c

  日期：——

  and efficient catalyst-oxidant combination in the chemoselective oxidation of thiols to disulfides and sulfides to sulfoxides. This magnetically separable catalyst was found to be reusable for five consecutive runs without appreciable change in the activity, as well as composition of the catalyst. The mechanism for the oxidation of thiols and sulfides has also been proposed.

  镍铁氧体纳米粒子-过氧化氢作为硫醇化学选择性氧化成二硫化物和硫化物成亚砜的绿色和有效的催化剂-氧化剂组合首次被证明。发现该磁性可分离的催化剂可连续五次重复使用，而活性以及催化剂的组成没有明显变化。还已经提出了硫醇和硫化物的氧化机理。