α-acetoxybenzyl phenyl sulfide | 60586-53-0

• 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: α-acetoxybenzyl phenyl sulfide
• 英文别名: phenyl(phenylthio)methyl acetate；(α-Acetoxy-benzyl)-phenyl-sulfid；acetic acid-(α-phenylsulfanyl-benzyl ester)；Essigsaeure-(α-phenylmercapto-benzylester)；[phenyl(phenylsulfanyl)methyl] acetate
• CAS: 60586-53-0
• 化学式: C₁₅H₁₄O₂S
• 分子量: 258.341
• InChiKey: IVZLIHGOKNMAQP-UHFFFAOYSA-N

物化性质

• 熔点：
  49-50 °C
• 沸点：
  143 °C(Press: 11 Torr)
• 密度：
  1.18±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.04
• 重原子数：
  18.0
• 可旋转键数：
  4.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.13
• 拓扑面积：
  26.3
• 氢给体数：
  0.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  α-acetoxybenzyl phenyl sulfide 、 disodium;carbonate 生成 苯甲醛
  参考文献：
  名称：

  JRIUCHIJIMA SHINOBU; SAKAKIBARA TERUO; TSUCHIHASHI GEN-ICHI, AGR. AND BIOL. CHEM. , 1976, 40, NO 7, 1369-1372

  摘要：

  DOI：
• 作为产物：
  描述：

  苯基双(苯硫基)甲烷 、 溶剂黄146 以80%的产率得到
  参考文献：
  名称：

  UGUEN, D., TETRAHEDRON LETT., 1984, 25, N 5, 541-542

  摘要：

  DOI：

文献信息

• Pummerer Reaction of Sulfoxides in Acetic Anhydride Catalyzed by Al-MCM-41
  作者：Suguru Ito、Yoshihiro Kubota、Masatoshi Asami

  DOI：10.1246/cl.150896

  日期：2016.1.5

  The Pummerer reaction of acetic anhydride with both alkyl aryl sulfoxides and dialkyl sulfoxides was efficiently promoted by a mesoporous aluminosilicate Al-MCM-41 to afford the corresponding α-ace...

  乙酸酐与烷基芳基亚砜和二烷基亚砜的Pummerer反应被介孔铝硅酸盐Al-MCM-41有效促进，得到相应的α-ace...
• Copper induced solvolysis of sulfur compounds
  作者：D. Uguen

  DOI：10.1016/s0040-4039(00)99932-5

  日期：1984.1

  The displacement of a phenylthio group by an acetate ion in some allylic or α-alcoxy sulfides and thioacetals was cleanly performed by treating them with a mixture of copper powder and cupric acetate in acetic acid.

  通过用铜粉和乙酸铜在乙酸中的混合物处理，可以干净地进行乙酸烯丙基或α-烷氧基硫化物和硫代乙缩醛中乙酸根离子对苯硫基的置换。
• Direct α-acyloxylation of organic sulfides with the hypervalent (diacyloxyiodo)benzene/tetra-n-butylammonium bromide (TBAB) reagent combination
  作者：Dan Zhu、Denghu Chang、Shaoyan Gan、Lei Shi

  DOI：10.1039/c6ra01799a

  日期：——

  A novel metal-free approach to directly synthesize α-acyloxy sulfides from readily available alkyl sulfides utilizing the hypervalent (diacyloxyiodo)benzene and TBAB reagent combination is reported. This transformation is characterized by its broad substrate scope in moderate to excellent yields, convenient operating conditions and outstanding functional group tolerance.

  报道了一种新颖的无金属方法，该方法利用超价（二酰氧基碘）苯和TBAB试剂的组合，从容易获得的烷基硫化物中直接合成α-酰氧基硫化物。这种转变的特征在于其广泛的底物范围，具有中等至优异的产率，便利的操作条件和出色的官能团耐受性。
• Horner; Kaiser, Justus Liebigs Annalen der Chemie, 1959, vol. 626, p. 19,20,24
  作者：Horner、Kaiser

  DOI：——

  日期：——
• Medium and structure effects on the anodic oxidation of aryl arylmethyl sulfides
  作者：Enrico Baciocchi、Cesare Rol、Emanuela Scamosci、Giovanni V. Sebastiani

  DOI：10.1021/jo00019a005

  日期：1991.9

  The anodic oxidation of a number of XC6H4CH2SC6H4Y has been investigated under a variety of conditions (AcOH/AcO-,AcOH/NO3-,AcOH/ClO4-,CH3CN/ClO4-) and the relative weight of the various reaction paths available to the intermediate radical cation (C-alpha-H deprotonation, C-S bond cleavage, attack on sulfur) evaluated via product analysis. It has been observed that in AcOH/AcO- (presence of a strong base) the main reaction is C-alpha-H deprotonation, which is also favored when X is an electron-withdrawing substituent and depressed by electron-donating Y. The C-S bond cleavage reaction is particularly important in CH3CN/ClO4-; its relative contribution is enhanced by an electron-donating X, which makes the benzyl carbocation more stable. The pathway leading to sulfoxides is favored in AcOH/NO3- and, to a lesser extent, in AcOH/ClO4-. Formation of sulfoxide is also favored when Y is an electron-donating group.