(4-chlorophenyl)(2-methoxyphenyl)sulfane | 14100-92-6

• 分子结构分类: 有机化合物 - 有机硫化合物 - 硫醚类
• 英文名称: (4-chlorophenyl)(2-methoxyphenyl)sulfane
• 英文别名: 1-Chloro-4-(2-methoxyphenyl)sulfanylbenzene
• CAS: 14100-92-6
• 化学式: C₁₃H₁₁ClOS
• 分子量: 250.749
• InChiKey: LQBOZQNHUNUXAJ-UHFFFAOYSA-N

物化性质

• 熔点：
  144-146 °C
• 沸点：
  349.9±27.0 °C(Predicted)
• 密度：
  1.26±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.6
• 重原子数：
  16
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.08
• 拓扑面积：
  34.5
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  (4-氯苯基硫)丙-2-酮 在 镍 sodium hydroxide 、 氢气 作用下， 生成 (4-chlorophenyl)(2-methoxyphenyl)sulfane
  参考文献：
  名称：

  Govindachari,T.R. et al., Indian Journal of Chemistry, 1966, vol. 4, p. 433 - 437

  摘要：

  DOI：

文献信息

• Visible-light-promoted synthesis of diaryl sulfides under air
  作者：Boseok Hong、Juyoung Lee、Anna Lee

  DOI：10.1016/j.tetlet.2017.06.006

  日期：2017.7

  A convergent, organocatalytic visible-light-mediated process for the synthesis of diaryl sulfides has been developed. A broad range of aryl thiols reacted with various aryl diazonium salts in the presence of eosin Y under air atmosphere to afford the desired diaryl sulfides in high yields. This novel and environmentally friendly method provides an alternative route to established synthetic approaches

  已经开发了一种收敛的，有机催化的可见光介导的合成二芳基硫的方法。在曙红Y存在下，在空气气氛下，各种各样的芳基硫醇与各种芳基重氮盐反应，以高收率得到所需的二芳基硫醚。这种新颖且环保的方法为建立合成方法提供了另一种途径。
• CuI‐catalyzed direct synthesis of diaryl thioethers from aryl boronic acids and arylsulfonyl chlorides
  作者：Keke Huang、Min Yang、Xiao‐Jing Lai、Xin Hu、Guanyinsheng Qiu、Jin‐Biao Liu

  DOI：10.1002/aoc.5385

  日期：2020.2

  A CuI‐catalyzed direct coupling of aryl boronic acids with arylsulfonyl chlorides for the preparation of diaryl thioethers was developed. The reaction is initiated by a PPh3 reduction of the arylsulfonyl chloride, followed by a CuI‐catalyzed C–S coupling with an aryl boronic acid. Various arylsulfonyl chlorides can directly serve as a sulfur source in this mild and efficient reaction giving the desired

  开发了CuI催化的芳基硼酸与芳基磺酰氯的直接偶联，用于制备二芳基硫醚。通过PPh 3还原芳基磺酰氯开始反应，然后CuI催化的C–S与芳基硼酸偶合。在这种温和而有效的反应中，各种芳基磺酰氯可直接用作硫源，以中等至良好的收率得到所需产物。而且，该实用方法也已经应用于芳基碘化物和乙酰丙酮的硫醚化。
• Dechalcogenization of Aryl Dichalcogenides to Synthesize Aryl Chalcogenides via Copper Catalysis
  作者：Yongqiang Wang、Jiedan Deng、Jinhong Chen、Fei Cao、Yongsheng Hou、Yuhang Yang、Xuemei Deng、Jinru Yang、Lingxi Wu、Xiangfeng Shao、Tao Shi、Zhen Wang

  DOI：10.1021/acscatal.9b04931

  日期：2020.2.21

  An application for dechalcogenization of aryl dichalcogenides via copper catalysis to synthesize aryl chalcogenides is disclosed. This approach is highlighted by the practical conditions, broad substrate scope, and good functional group tolerance with several sensitive groups such as aldehyde, ketone, ester, amide, cyanide, alkene, nitro, and methylsulfonyl. Furthermore, the robustness of this methodology

  公开了一种通过铜催化将芳族二硫属元素进行脱硫反应以合成芳基硫属元素化物的应用。实际条件，广泛的底物范围以及对几个敏感基团（如醛，酮，酯，酰胺，氰化物，烯烃，硝基和甲基磺酰基）的良好官能团耐受性突出了该方法。此外，该方法的鲁棒性通过雌酮的后期修饰和伏替西汀的合成来描述。值得注意的是，通过该方案成功地完成了在较温和条件下具有较大环张力的更具挑战性的有机材料的合成，以及某些不能通过金属催化的芳基卤素偶合反应合成的含卤素的二芳基硫醚的合成。
• Reaction of Arynes with Sulfoxides
  作者：Hong-Ying Li、Li-Juan Xing、Mei-Mei Lou、Han Wang、Rui-Hua Liu、Bin Wang

  DOI：10.1021/ol5036326

  日期：2015.3.6

  A S–O bond insertion reaction of sulfoxides with arynes is reported. This reaction represents a rare instance of semipolar single bond insertion in aryne chemistry. The study of mechanism indicates that a sulfur ylide triggered by aryne is the key intermediate, which further transfers its methylene group to carbonyl compounds to give epoxides and thioethers through a sequential process.

  据报道亚砜与芳烃的AS-O键插入反应。该反应代表了芳烃化学中半极性单键插入的罕见情况。机理研究表明，芳烃引发的硫叶立德是关键中间体，它通过一个连续的过程进一步将其亚甲基转移至羰基化合物，从而生成环氧化物和硫醚。
• One-Pot, Three-Component Assembly of Sulfides Using a Sulfoxide Reagent as a Sulfur Dication Equivalent
  作者：Fumito Saito、Simon Euteneuer

  DOI：10.1021/acs.orglett.3c02301

  日期：2023.8.18

  We report a one-pot, three-component synthesis of sulfides by exploiting a sulfoxide reagent as a formal sulfur dication equivalent. Our protocol consists of three simple chemical operations involving two Grignard reagents and trimethylsilyl chloride (TMSCl) to sequentially form sulfenate anions, sulfenate esters, and sulfides. We demonstrate a wide range of Grignard reagents to be coupled, thereby

  我们报告了通过利用亚砜试剂作为形式的硫双标等价物来一锅三组分合成硫化物。我们的方案由三个简单的化学操作组成，涉及两种格氏试剂和三甲基氯硅烷 (TMSCl)，依次形成磺酸根阴离子、磺酸酯和硫化物。我们展示了多种可偶联的格氏试剂，从而可以模块化、无硫醇合成硫化物，包括二烯基和烯基-炔基硫化物。