[2-methoxy-6-[(1S)-1-methylsulfanylethyl]phenyl] selenohypobromite | 819852-45-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: [2-methoxy-6-[(1S)-1-methylsulfanylethyl]phenyl] selenohypobromite
• CAS: 819852-45-4
• 化学式: C₁₀H₁₃BrOSSe
• 分子量: 340.143
• InChiKey: XKIZCSBMBODUQK-ZETCQYMHSA-N

物化性质

• 沸点：
  373.1±42.0 °C(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.76
• 重原子数：
  14
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  34.5
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  [2-methoxy-6-[(1S)-1-methylsulfanylethyl]phenyl] selenohypobromite 以 甲醇 、 二氯甲烷 为溶剂， 反应 12.0h， 生成 (S)-1-Methoxy-2-[2-methoxy-6-((S)-1-methylsulfanyl-ethyl)-phenylselanyl]-heptan-3-ol
  参考文献：
  名称：

  Kinetic Resolution of Allylic Alcohols Promoted by Electrophilic Selenium Reagents

  摘要：

  The first example of a kinetic resolution process promoted by an electrophilic selenium reagent is reported. Racemic allylic alcohols react with half equivalents of a selenenylating agent in methanol leading to the regiospecific formation, of the corresponding addition products with a very high level of facial selectivity (98% de). The unreacted alcohol can be recovered in a optically enriched form (92% ee).

  DOI：

  10.1080/10426500590906355
• 作为产物：
  描述：

  bis[2-methoxy-6-[(1S)-1-(methythio)ethyl]phenyl]diselenide 在 溴 作用下， 以 乙醚 为溶剂， 生成 [2-methoxy-6-[(1S)-1-methylsulfanylethyl]phenyl] selenohypobromite
  参考文献：
  名称：

  Kinetic Resolution of Allylic Alcohols Promoted by Electrophilic Selenium Reagents

  摘要：

  The first example of a kinetic resolution process promoted by an electrophilic selenium reagent is reported. Racemic allylic alcohols react with half equivalents of a selenenylating agent in methanol leading to the regiospecific formation, of the corresponding addition products with a very high level of facial selectivity (98% de). The unreacted alcohol can be recovered in a optically enriched form (92% ee).

  DOI：

  10.1080/10426500590906355

文献信息

• A Chiral Electrophilic Selenium Reagent To Promote the Kinetic Resolution of Racemic Allylic Alcohols
  作者：Marcello Tiecco、Lorenzo Testaferri、Claudio Santi、Cristina Tomassini、Rosaria Bonini、Francesca Marini、Luana Bagnoli、Andrea Temperini

  DOI：10.1021/ol048001+

  日期：2004.12.1

  [reaction: see text] The first example of a kinetic resolution process promoted by electrophilic selenium reagents is reported. Racemic allylic alcohols react with half equivalents of a selenenylating agent in methanol leading to the regiospecific formation of the corresponding addition products with a very high level of facial selectivity (from 95:5 to 98:2 dr). The unreacted alcohols can be recovered

  [反应：见正文]报告了由亲电子硒试剂促进的动力学拆分过程的第一个例子。外消旋烯丙醇与甲醇中半当量的硒烯化剂反应，导致具有非常高的面部选择性（从95：5至98：2 dr）的相应加成产物区域特异性形成。未反应的醇可以光学富集的形式（从90％到94％ee）回收。