S-phenyl 2-hydroxy-2-phenyl(thioethanoate) | 65544-99-2

• 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-phenyl 2-hydroxy-2-phenyl(thioethanoate)
• 英文别名: S-phenyl hydroxy-phenyl-thioacetate；S-phenyl 2-hydroxy-2-phenylethanethioate
• CAS: 65544-99-2
• 化学式: C₁₄H₁₂O₂S
• 分子量: 244.314
• InChiKey: AWPMRQAOIWVCQY-UHFFFAOYSA-N

物化性质

• 熔点：
  58-61 °C
• 沸点：
  405.2±38.0 °C(Predicted)
• 密度：
  1.26±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.04
• 重原子数：
  17.0
• 可旋转键数：
  3.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  37.3
• 氢给体数：
  1.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  S-phenyl 2-hydroxy-2-phenyl(thioethanoate) 在 chiral vanadium(V) 氧气 作用下， 以 甲苯 为溶剂， 反应 7.0h， 生成 (R)-S-phenyl hydroxy-phenyl-thioacetate 、 (S)-S-phenyl hydroxy-phenyl-thioacetate 、 phenyl phenylthioglyoxylate
  参考文献：
  名称：

  Asymmetric Aerobic Oxidation of α-Hydroxy Acid Derivatives by C₄-Symmetric, Vanadate-Centered, Tetrakisvanadyl(V) Clusters Derived from N-Salicylidene-α-aminocarboxylates

  摘要：

  A series of chiral vanadyl(V) methoxides bearing 3-t-butyl-5-substituted N-salicylene-L-valinate and L-t-leucinate as chiral auxiliaries has been prepared. In all cases except the 3,5-di-t-butyl analogue, they exist as monomers both in solution and in the single crystal state. In the case of the 3,5-di-t-butyl analogue, the architectural nature of the vanadyl(V) complex highly depends on the base used during the complex formation event. A pentanuclear C-4-symmetric complex was formed when potassium salts were employed instead of the corresponding sodium salts. A central vanadate(V) unit serves to grip four identical chiral monomeric vanadyl(V) units together, by which a potassium ion sits on top of the four flanking units through carbonyl coordinations and serves to hold the whole cluster by cooperation with the central vanadate(V) unit. In comparison with the corresponding monomeric vanadyl(V) methoxide complex, the cluster complex was utilized to facilitate the asymmetric aerobic oxidations of various racemic alpha-hydroxyesters, -amides, and -thioesters with excellent selectivity factors (k(rel) 40 to >500).

  DOI：

  10.1021/jo070575f
• 作为产物：
  描述：

  扁桃酸 在 4-二甲氨基吡啶 作用下， 以 四氢呋喃 为溶剂， 生成 S-phenyl 2-hydroxy-2-phenyl(thioethanoate)
  参考文献：
  名称：

  Gais,H.-J.; Lied,T., Angewandte Chemie, 1978, vol. 90, p. 283 - 285

  摘要：

  DOI：

文献信息

• Preparation of 2-halogeno S-phenyl thioesters from 2-phenylsulphony -2-phenylthiooxiranes. Crystal structures of 2-phenylsulphonyloxiranes
  作者：Cheryl T. Hewkin、Richard F. W. Jackson、William Clegg

  DOI：10.1039/p19910003091

  日期：——

  the preparation of 3,3-dialkyl2-phenylsulphonyl-2-phenylthiooxiranes. The oxiranes 4 react with lithium or magnesium halides to give good yields of 2-halogeno S-phenyl thioesters 5, 6 and 7. 2-lodo S-phenyl thioesters 7 are deiodinated by further treatment with magnesium iodide. In an analogous manner, 2-bromo Smethyl thioesters 15 and a 2-bromo Se-phenyl selenoester 17b are also prepared from the

  1-苯磺酰基-1- phenylthioalkenes 8与高立体选择性为（制备ê在一个单釜法）异构体通过的反应苯基苯硫基甲基砜9与醛，随后消除。用叔丁基氢过氧化物锂对这些烯烃进行亲核环氧化，得到2-苯基磺酰基-2-苯基硫代肟酸酯4，为单一的非对映异构体，而未检测到苯硫基官能团的氧化。还可以通过用丁基锂处理苯磺酰基氧肟酮13，然后再用二苯基二硫化物来制备环氧乙烷，这使得可以制备3,3-二烷基2-苯基磺酰基-2-苯基硫代环氧乙烷。oxiranes 4与锂或卤化镁反应得到的2-卤代良好的收率小号-苯基硫酯5，6和7。通过用碘化镁进一步处理使2-卤代S-苯基硫代酯7脱碘。以类似的方式，也从相应的肟酸酯制备2-溴S甲基硫代酯15和2-溴Se-苯基硒酸酯17b。2-苯基磺酰氧杂环戊烷4b，13e和14b的X射线晶体结构，表明远离磺酰基的C-O键的一致延长，以及与磺酰基相邻的C-O键的显着缩短。
• Transition‐Metal‐Free Reduction of <i>α</i> ‐Keto Thioesters with Hydrosilanes at Room Temperature: Divergent Synthesis through Reagent‐Controlled Chemoselectivities
  作者：Rajib Maity、Bhanuranjan Das、Indrajit Das

  DOI：10.1002/adsc.201900222

  日期：2019.5.14

  acid as a promoter can be used for the reagent‐controlled chemoselective reduction at room temperature of conjugated C=C bond, enone moiety, or the carbonyl of (β,γ‐unsaturated) α‐keto thioesters, providing facile access to β,γ‐saturated α‐keto thioesters, α‐hydroxy thioesters, or silyl ethers. The reaction pathway and the chemoselectivity can be fine‐tuned through the judicious choice of the hydrosilane

  氢硅烷与布朗斯台德酸或路易斯酸作为促进剂的组合可用于在室温下进行试剂控制的化学选择还原反应，以还原共轭C = C键，烯酮部分或（β，γ-不饱和）α-酮的羰基硫酯，可轻松获得β，γ-饱和的α-酮硫代酯，α-羟基硫代酯或甲硅烷基醚。可以通过明智地选择氢化硅烷或反应条件来微调反应途径和化学选择性。该反应可耐受包括不稳定的硫酯在内的各种官能团，并且通常以中等至极好的收率获得产物。不对称硫醚也可以使用PMHS和催化性B（C 6 F 5）3合成通过两个羰基的还原性脱氧。β，γ-不饱和α-羟基硫代酯和β，γ-饱和α-酮硫代酯的饱和α-酮酰胺的胺介导和无偶联剂的合成突出了其适用性。