S-(p-tolyl) 2-(4-chlorophenyl)ethanethioate

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯硫酚酯
• 英文名称: S-(p-tolyl) 2-(4-chlorophenyl)ethanethioate
• 英文别名: S-(4-methylphenyl) 2-(4-chlorophenyl)ethanethioate
• 化学式: C₁₅H₁₃ClOS
• 分子量: 276.787
• InChiKey: XYBHIFBVFZPJLB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.8
• 重原子数：
  18
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.13
• 拓扑面积：
  42.4
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  S-(p-tolyl) 3-(4-chlorophenyl)oxirane-2-carbothioate 在 1,3-双(二苯基膦)丙烷 、 三乙胺 、 nickel dichloride 作用下， 以 甲苯 为溶剂， 以58 %的产率得到S-(p-tolyl) 2-(4-chlorophenyl)ethanethioate
  参考文献：
  名称：

  镍催化合成苄基硫酯和苄基硫醚：环氧硫酯串联工艺的单脱羰基和双脱羰基/重排

  摘要：

  描述了一种用于 Ni 催化的环氧硫酯脱羰基和重排的策略。通过改变催化条件选择性地实现单脱羰基和双脱羰基反应，从而以中等至优异的收率生产苄基硫酯和苄基硫醚。新协议以直接的方式为 C-S 键的形成提供了一条简便的途径。

  DOI：

  10.1016/j.tet.2023.133437

文献信息

• Palladium‐Catalyzed Thiocarbonylation of Benzyl Chlorides with Sulfonyl Chlorides for the Synthesis of Arylacetyl Thioesters
  作者：Wei Wang、Xinxin Qi、Xiao‐Feng Wu

  DOI：10.1002/adsc.202100112

  日期：2021.5.18

  A convenient procedure for the synthesis of thioesters has been developed via a palladium-catalyzed thiocarbonylation of benzyl chlorides with sulfonyl chlorides. Various arylacetyl thioesters were produced in good yields by using sulfonyl chlorides as an odorless sulfur source. Furthermore, W(CO)6 exhibited dual roles as both a solid CO surrogate and reductant here.

  通过苄基氯与磺酰氯的钯催化的硫代羰基化，已经开发了一种方便的合成硫酯的方法。通过使用磺酰氯作为无味硫源，以高收率生产了各种芳基乙酰基硫代酯。此外，W（CO）6在这里既表现出固体CO替代物又具有还原剂的双重作用。
• Autocatalytic Synthesis of Thioesters via Thiocarbonylation of <i>gem</i>-Difluoroalkenes
  作者：Xinpeng Jiang、Guan Wang、Zicong Zheng、Xiaohui Yu、Ye Hong、Haoqi Xia、Chuanming Yu

  DOI：10.1021/acs.orglett.0c03860

  日期：2020.12.18

  Herein, we report a new method for the synthesis of acyethanethioates via thiocarbonylation of gem-difluoroalkenes with thiols. This reaction provides a new pathway to prepare thioesters under mild conditions without the use of any additives. Mechanistic studies revealed that in situ generated HF facilitated the C-F bond cleavage in an autocatalytic manner.
• Nickel-catalyzed synthesis of benzyl thioesters and benzyl thioethers: Mono and double decarbonylations/rearrangement of epoxy thioester tandem process
  作者：Rui Tian、Jia-Xin Li、Yong-Ming Zhu

  DOI：10.1016/j.tet.2023.133437

  日期：2023.6

  A strategy for Ni-catalyzed decarbonylation and rearrangement of epoxy thioester is described. Mono- and double-decarbonylations were selectively achieved by changing catalytic condition, leading to the production of benzyl-thioesters and benzyl-thioethers in moderate to excellent yields. The new protocol enables a facile route for C–S bond formation in a straightforward fashion.

  描述了一种用于 Ni 催化的环氧硫酯脱羰基和重排的策略。通过改变催化条件选择性地实现单脱羰基和双脱羰基反应，从而以中等至优异的收率生产苄基硫酯和苄基硫醚。新协议以直接的方式为 C-S 键的形成提供了一条简便的途径。