phenyl (p-toluenesulfonyl)acetate

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚酯
• 英文名称: phenyl (p-toluenesulfonyl)acetate
• 英文别名: phenyl 2-tosylacetate；phenyl (tolylsulfonyl)acetate；Phenyl 2-(4-methylphenyl)sulfonylacetate；phenyl 2-(4-methylphenyl)sulfonylacetate
• 化学式: C₁₅H₁₄O₄S
• 分子量: 290.34
• InChiKey: ZBILGXUBFMMFRG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  20
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.13
• 拓扑面积：
  68.8
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  tetracyanothiophene 、 phenyl (p-toluenesulfonyl)acetate 在 sodium hydride 作用下， 以 四氢呋喃 、 mineral oil 为溶剂， 反应 1.0h， 以78%的产率得到sodium 1-(tert-butoxycarbonyl)-2,3,4,5-tetracyanocyclopentadienide
  参考文献：
  名称：

  由四苯甲基噻吩和砜合成功能化四苯甲基环戊二烯化物

  摘要：

  四苯并噻吩并四氰基-1,4-二硫氨酸与离去基团取代的碳亲核试剂如乙基苯磺酰基乙酸酯反应，通过推定的缩合和脱硫途径以中等至高收率提供取代的四氰基环戊二烯基钠衍生物。在CP阴离子环在随后的官能团转化反应提供各种C语言5 R（CN）4 -衍生物。

  DOI：

  10.1021/jo401946j
• 作为产物：
  描述：

  phenyl diazoacetate 、 对甲苯磺酰肼 在 四丁基碘化铵 作用下， 以 异丙醇 为溶剂， 反应 24.0h， 以62%的产率得到phenyl (p-toluenesulfonyl)acetate
  参考文献：
  名称：

  Bu₄NI-Catalyzed Cross-Coupling between Sulfonyl Hydrazides and Diazo Compounds To Construct β-Carbonyl Sulfones Using Molecular Oxygen

  摘要：

  A new cross-coupling reaction between sulfonyl hydrazides and diazo compounds has been established, leading to a variety of beta-carbonyl sulfones in good yields. This methodology was distinguished by simple manipulation, easily available starting materials, and wide substrate scope. A plausible mechanism involving a radical process was proposed based upon the experimental observations and literature.

  DOI：

  10.1021/acs.orglett.6b02532

文献信息

• Bu₄NI-Catalyzed Cross-Coupling between Sulfonyl Hydrazides and Diazo Compounds To Construct β-Carbonyl Sulfones Using Molecular Oxygen
  作者：Yaxiong Wang、Liang Ma、Meihua Ma、Hao Zheng、Ying Shao、Xiaobing Wan

  DOI：10.1021/acs.orglett.6b02532

  日期：2016.10.7

  A new cross-coupling reaction between sulfonyl hydrazides and diazo compounds has been established, leading to a variety of beta-carbonyl sulfones in good yields. This methodology was distinguished by simple manipulation, easily available starting materials, and wide substrate scope. A plausible mechanism involving a radical process was proposed based upon the experimental observations and literature.
• Synthesis of Functionalized Tetracyanocyclopentadienides from Tetracyanothiophene and Sulfones
  作者：Takeo Sakai、Shohei Seo、Junpei Matsuoka、Yuji Mori

  DOI：10.1021/jo401946j

  日期：2013.11.1

  Tetracyanothiophene and tetracyano-1,4-dithiin react with a leaving group substituted carbon nucleophile such as ethyl benzenesulfonylacetate to afford substituted tetracyanocyclopentadienyl sodium derivatives in moderate to high yields through a putative condensation and desulfurization pathway. Subsequent functional-group transformation reactions on the Cp anion ring provided various C5R(CN)4– derivatives

  四苯并噻吩并四氰基-1,4-二硫氨酸与离去基团取代的碳亲核试剂如乙基苯磺酰基乙酸酯反应，通过推定的缩合和脱硫途径以中等至高收率提供取代的四氰基环戊二烯基钠衍生物。在CP阴离子环在随后的官能团转化反应提供各种C语言5 R（CN）4 -衍生物。