Phenyl-dimethyl-carbinyl-thiolbenzoat | 7429-01-8

• 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: Phenyl-dimethyl-carbinyl-thiolbenzoat
• 英文别名: S-(2-phenylpropan-2-yl) benzenecarbothioate
• CAS: 7429-01-8
• 化学式: C₁₆H₁₆OS
• 分子量: 256.368
• InChiKey: CSJVRRUXXSPTQM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.4
• 重原子数：
  18
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.19
• 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：

  2-苯基-2-丙基苯并二硫 在 偶氮二异丁腈 、 氧气 作用下， 以 苯 为溶剂， 反应 4.0h， 生成 Phenyl-dimethyl-carbinyl-thiolbenzoat
  参考文献：
  名称：

  Radical-induced oxidation of RAFT agents-A kinetic study

  摘要：

  AbstractRadical‐induced oxidation of reversible addition‐fragmentation chain transfer (RAFT) agents is investigated with respect to the effect of molecular structure on oxidation rate. The radicals are generated by homolysis of either azobisisobutyronitrile or alkoxyamine and transformed in situ immediately into peroxy radicals through transfer to molecular oxygen. It is found that the oxidation rate depends on the structure of Z‐ and R‐group of thiocarbonylthio compounds. For dithioesters with identical Z‐phenyl substituent, the oxidation rate decreases in the order of cyanoisopropyl (C(Me)2CN) > cumyl (C(Me)2Ph) > phenylethyl (CH(Me)Ph) > 2‐methoxy‐1‐methyl‐2‐oxoethyl (CH(Me) C(O)OCH3) > benzyl (CH2Ph). For dithioesters with identical R‐group, the oxidation rate decreases in the order of Z = phenyl− ∼ benzyl− > RS− (trithiocarbonates) > RO− (xanthates). The stability of the RAFT agents toward oxidation correlates well with the chain transfer abilities as those previously reported by Rizzardo and coworkers. The priority of the oxidation reaction over the RAFT process, and the subsequent influence on RAFT polymerization are also investigated. © 2011 Wiley Periodicals, Inc. J Polym Sci Part A: Polym Chem, 2011

  DOI：

  10.1002/pola.24554

文献信息

• Montmorillonite K 10-catalyzed regioselective addition of thiols and thiobenzoic acids onto olefins: an efficient synthesis of dithiocarboxylic esters
  作者：Subbareddy Kanagasabapathy、Arumugam Sudalai、Brian C Benicewicz

  DOI：10.1016/s0040-4039(01)00570-6

  日期：2001.6

  The addition of thiols and thiobenzoic acids onto olefins proceeded regioselectively in a Markovnikov manner in the presence of Montmorillonite K 10 (Mont K 10) clay as the catalyst to afford thioethers and thiocarboxylic S-esters, while high selectivity to anti-Markovnikov products was realized in the absence of any catalyst. Treatment of the esters with Lawesson's reagent provided the corresponding

  在蒙脱石K 10（Mont K 10）粘土作为催化剂提供硫醚和硫代羧酸S酯的存在下，以马尔科夫尼科夫方式选择性地将硫醇和硫代苯甲酸加到烯烃上，同时实现了对反马尔科夫尼科夫产物的高选择性。在没有任何催化剂的情况下。用Lawesson试剂处理酯类，可以高收率得到相应的二硫代羧酸酯。
• Application of Halogen-Bonding Catalysis for Markovnikov-Type Hydrothiolation of Alkenes
  作者：Zhankui Sun、Xue Zhang、Nuoyu Liang、Ruining Li

  DOI：10.1055/a-1984-9105

  日期：2023.3

  Carbon–sulfur bond-formation reactions are applied widely in organic synthesis and chemical biology. Hydrothiolation of alkenes provides a direct way to build carbon–sulfur bonds. Most known methods proceed via radical processes and result in anti-Markovnikov-type products. Herein, we demonstrate that I2 catalyzes the hydrothiolation of alkenes and provides Markovnikov-type products in good to excellent

  碳硫键形成反应在有机合成和化学生物学中有着广泛的应用。烯烃的氢硫醇化提供了建立碳硫键的直接方法。大多数已知方法通过激进过程进行并产生反马尔可夫尼科夫型产品。在此，我们证明 I 2催化烯烃的氢硫醇化反应，并以良好至优异的收率提供 Markovnikov 型产品。滴定研究表明硫醇被 I 2通过卤键激活。这种无金属反应具有绿色温和、功能耐受性高、底物适用范围广、原子经济等优点。它的应用在肽合成中得到进一步证明。
• Leaving group effects in solvolysis reactions
  作者：Rodney L. Buckson、Stanley Glen Smith

  DOI：10.1021/jo01278a028

  日期：1967.3
• Radical-induced oxidation of RAFT agents-A kinetic study
  作者：Changxi Li、Junpo He、Yanwu Zhou、Yuankai Gu、Yuliang Yang

  DOI：10.1002/pola.24554

  日期：2011.3.15

  AbstractRadical‐induced oxidation of reversible addition‐fragmentation chain transfer (RAFT) agents is investigated with respect to the effect of molecular structure on oxidation rate. The radicals are generated by homolysis of either azobisisobutyronitrile or alkoxyamine and transformed in situ immediately into peroxy radicals through transfer to molecular oxygen. It is found that the oxidation rate depends on the structure of Z‐ and R‐group of thiocarbonylthio compounds. For dithioesters with identical Z‐phenyl substituent, the oxidation rate decreases in the order of cyanoisopropyl (C(Me)2CN) > cumyl (C(Me)2Ph) > phenylethyl (CH(Me)Ph) > 2‐methoxy‐1‐methyl‐2‐oxoethyl (CH(Me) C(O)OCH3) > benzyl (CH2Ph). For dithioesters with identical R‐group, the oxidation rate decreases in the order of Z = phenyl− ∼ benzyl− > RS− (trithiocarbonates) > RO− (xanthates). The stability of the RAFT agents toward oxidation correlates well with the chain transfer abilities as those previously reported by Rizzardo and coworkers. The priority of the oxidation reaction over the RAFT process, and the subsequent influence on RAFT polymerization are also investigated. © 2011 Wiley Periodicals, Inc. J Polym Sci Part A: Polym Chem, 2011