S-t-butyl oxo-p-tolyl-thioacetate | 959161-61-6

• 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-t-butyl oxo-p-tolyl-thioacetate
• CAS: 959161-61-6
• 化学式: C₁₃H₁₆O₂S
• 分子量: 236.335
• InChiKey: DKGZNKFUAZYDBL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.24
• 重原子数：
  16.0
• 可旋转键数：
  2.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  34.14
• 氢给体数：
  0.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  S-t-butyl oxo-p-tolyl-thioacetate 在 chiral vanadium(V) sodium tetrahydroborate 、 氧气 作用下， 以 四氢呋喃 、 甲苯 为溶剂， 反应 90.0h， 生成 (R)-S-t-butyl hydroxy-p-tolyl-thioacetate
  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：

  4-甲基苯基乙醛酸 在 草酰氯 、 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 0.5h， 生成 S-t-butyl oxo-p-tolyl-thioacetate
  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

文献信息

• Phase-transfer catalysed asymmetric synthesis of α-chiral tetrasubstituted α-aminothioesters
  作者：Yasushi Yoshida、Reina Kasuya、Takashi Mino、Masami Sakamoto

  DOI：10.1039/d1ob00829c

  日期：——

  α-Tetrasubstituted-α-amino thioesters were synthesised through chiral phase-transfer catalysed Michael reaction of imino thioesters in up to 97% yield with up to 81% ee.

  α-四取代-α-氨基硫酯通过手性相转移催化的Michael反应合成，产率高达97%，对映选择性高达81%。