(phenylsulfenyl)zinc bromide | 1449477-04-6

• 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: (phenylsulfenyl)zinc bromide
• 英文别名: phenylthiozinc(II) bromide；(Phenylsulfenyl)ZINC bromide；benzenethiolate;bromozinc(1+)
• CAS: 1449477-04-6
• 化学式: Br*C₆H₅S*Zn
• 分子量: 254.466
• InChiKey: MZSOUYFWHHTVHJ-UHFFFAOYSA-L

计算性质

• 辛醇/水分配系数(LogP)：
  -1.41
• 重原子数：
  9
• 可旋转键数：
  0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  1
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (phenylsulfenyl)zinc bromide 、 methyloxirane 以 水 为溶剂， 反应 0.25h， 以70%的产率得到1-(苯基硫代)丙烷-2-醇
  参考文献：
  名称：

  “On-water” thiolysis of epoxides promoted by PhSZnBr

  摘要：

  The synthesis of a new bench-stable and odorless zinc thiolate is here reported. The thiolysis of epoxides effected using this reagent showed a considerable rate acceleration of the reaction when effected in "on-water" conditions. In addition, the reactions evidenced a good regioselectivity combining the advantage of the procedures effected in organic solvent with those effected using Lewis acid catalysis.[GRAPHICS].

  DOI：

  10.1080/17415993.2013.781604
• 作为产物：
  描述：

  phenylsulfenyl bromide 在 锌 作用下， 以 四氢呋喃 为溶剂， 以70%的产率得到(phenylsulfenyl)zinc bromide
  参考文献：
  名称：

  “On-water” thiolysis of epoxides promoted by PhSZnBr

  摘要：

  The synthesis of a new bench-stable and odorless zinc thiolate is here reported. The thiolysis of epoxides effected using this reagent showed a considerable rate acceleration of the reaction when effected in "on-water" conditions. In addition, the reactions evidenced a good regioselectivity combining the advantage of the procedures effected in organic solvent with those effected using Lewis acid catalysis.[GRAPHICS].

  DOI：

  10.1080/17415993.2013.781604

文献信息

• Synthesis of Thiol Esters Using PhSZnBr as Sulfenylating Agent: A DFT-Guided Optimization of Reaction Conditions
  作者：Luca Sancineto、Caterina Tidei、Luana Bagnoli、Francesca Marini、Vito Lippolis、Massimiliano Arca、Eder João Lenardão、Claudio Santi

  DOI：10.1002/ejoc.201600366

  日期：2016.6

  The use of PhSZnBr as sulfenylating agent in a solvent-free protocol to prepare thiol esters in excellent yields from acyl chlorides is reported. The products were efficiently obtained by grinding the neat reagents for 5 min in a mortar. DFT calculations showed that the coordination of solvent molecules to the metal center of PhSZnBr results in the destabilization of the frontier MOs, thus reducing

  报道了在无溶剂方案中使用 PhSZnBr 作为亚磺酰化剂从酰氯以优异的产率制备硫羟酸酯。通过在研钵中研磨纯试剂 5 分钟，有效地获得了产品。DFT 计算表明，溶剂分子与 PhSZnBr 金属中心的配位导致前沿 MO 的不稳定，从而与无溶剂条件相比降低了对酰氯的反应性。提出了基于酰氯的羰基与 PhSZnBr 金属中心配位的可能机制。
• “<i>On-water</i>” thiolysis of epoxides promoted by PhSZnBr
  作者：Simona Propersi、Caterina Tidei、Luana Bagnoli、Francesca Marini、Lorenzo Testaferri、Claudio Santi

  DOI：10.1080/17415993.2013.781604

  日期：2013.12.1

  The synthesis of a new bench-stable and odorless zinc thiolate is here reported. The thiolysis of epoxides effected using this reagent showed a considerable rate acceleration of the reaction when effected in "on-water" conditions. In addition, the reactions evidenced a good regioselectivity combining the advantage of the procedures effected in organic solvent with those effected using Lewis acid catalysis.[GRAPHICS].