S-Isopropyl 2-oxo-2-phenylethanethioate

• 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: S-Isopropyl 2-oxo-2-phenylethanethioate
• 英文别名: S-isopropyl oxo-phenyl-thioacetate；S-propan-2-yl 2-oxo-2-phenylethanethioate
• 化学式: C₁₁H₁₂O₂S
• 分子量: 208.281
• InChiKey: RIWIXGBNJZQCNT-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  14
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  59.4
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  S-Isopropyl 2-oxo-2-phenylethanethioate 在 三乙基硅烷 、 三氟乙酸 作用下， 反应 0.17h， 以97%的产率得到S-isopropyl 2-hydroxy-2-phenylethanethioate
  参考文献：
  名称：

  室温下用氢硅烷对α-酮基硫代酸酯进行无过渡金属还原：通过试剂控制的化学选择性进行合成

  摘要：

  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。

  DOI：

  10.1002/adsc.201900222
• 作为产物：
  描述：

  氧代(苯基)乙酰氯 、 异丙硫醇 在 三乙胺 作用下， 以 乙醚 为溶剂， 以75%的产率得到S-Isopropyl 2-oxo-2-phenylethanethioate
  参考文献：
  名称：

  羧酸酯的 ESR 研究。第 13 部分——2-氧代-碳硫酸酯和 2-氧-碳二硫酸酯的自由基阴离子的电子自旋共振光谱和分子轨道计算

  摘要：

  烷基α-氧代碳硫酸酯和α-氧代碳二硫代的自由基阴离子是通过原位电还原产生的。根据 ESR 谱和半经验（McLachlan 型和 AM1）MO 计算讨论了它们的自旋密度分布和配置。

  DOI：

  10.1002/mrc.1260321011

文献信息

• Direct Access to 2-Thioxooxazolidin-4-ones and Oxazolidine-2,4-diones from α-Keto Thioesters through Thiolate Transfer
  作者：Rajib Maity、Sandip Naskar、Kanchan Mal、Sandipa Biswas、Indrajit Das

  DOI：10.1002/adsc.201701020

  日期：2017.12.19

  We report a direct synthesis of 2‐thioxooxazolidin‐4‐ones and oxazolidine‐2,4‐diones from α‐keto thioesters with sodium thiocyanate or potassium cyanate, respectively. The reactions proceed through nucleophilic substitution of a thioester with thiocyanate/cyanate anion, thiolate anion addition to carbonyl carbon, and subsequent intramolecular C−O heterocyclization.

  我们报道了分别由α-酮硫酯与硫氰酸钠或氰酸钾直接合成2-thioxooxazolidlin-4-ones和oxazolidine-2,4-diones。反应通过硫氰酸盐/氰酸盐阴离子的硫酯的亲核取代，向羰基碳上的硫醇盐阴离子的亲核取代以及随后的分子内C-O杂环化而进行。
• Asymmetric Aerobic Oxidation of α-Hydroxy Acid Derivatives by <i>C</i>₄-Symmetric, Vanadate-Centered, Tetrakisvanadyl(V) Clusters Derived from <i>N</i>-Salicylidene-α-aminocarboxylates
  作者：Chien-Tien Chen、Sampada Bettigeri、Shiue-Shien Weng、Vijay D. Pawar、Ya-Hui Lin、Cheng-Yuan Liu、Way-Zen Lee

  DOI：10.1021/jo070575f

  日期：2007.10.1

  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).
• ESR studies on carboxylic esters. Part 13—electron spin resonance spectroscopy and molecular orbital calculations on the radical anions of 2-oxo-carbothioate and 2-oxo-carbodithioate esters
  作者：J. Gassmann、H. Günther、K. Osternack、A. Sawluk、K. Thimm、J. Voss

  DOI：10.1002/mrc.1260321011

  日期：1994.10

  Radical anions of alkyl α‐oxocarbothioates and α‐oxocarbodithioates are generated by in situ electroreduction. Their spin density distribution and configuration are discussed in terms of the ESR spectra and semi‐empirical (McLachlan‐type and AM1) MO calculations.

  烷基α-氧代碳硫酸酯和α-氧代碳二硫代的自由基阴离子是通过原位电还原产生的。根据 ESR 谱和半经验（McLachlan 型和 AM1）MO 计算讨论了它们的自旋密度分布和配置。
• 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。