acetoxy-p-tolyl-acetic acid | 145297-16-1

• 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: acetoxy-p-tolyl-acetic acid
• 英文别名: Acetoxy-p-tolyl-essigsaeure；2-Acetyloxy-2-(4-methylphenyl)acetic acid
• CAS: 145297-16-1；91143-62-3
• 化学式: C₁₁H₁₂O₄
• 分子量: 208.214
• InChiKey: BQMUZEVJRMGICP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  15
• 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：
  63.6
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  acetoxy-p-tolyl-acetic acid 、 三甲基硅烷化重氮甲烷 以 甲醇 、 乙醚 为溶剂， 反应 1.0h， 生成 methyl (+/-)-α-acetoxy-α-(4-methylphenyl)acetate
  参考文献：
  名称：

  Synthesis of Arylglycine and Mandelic Acid Derivatives through Carboxylations of α-Amido and α-Acetoxy Stannanes with Carbon Dioxide

  摘要：

  Incorporation reactions of carbon dioxide (CO2) with N-Boc-alpha\-amido and a-acetoxy stannanes were developed using CsF as a mild tin activator. Monoprotected alpha-amido stannanes could be used, and the corresponding arylglycine derivatives were obtained in moderate-to-high yields under 1 MPa (10 atm) of CO2 pressure. alpha-Acetoxy stannanes also underwent carboxylation to afford mandelic acid derivatives in excellent yields under ambient CO2 pressure. Both transformations enabled the synthesis of alpha-tertiary and alpha-quaternary carboxylic acid derivatives. In addition, the chirality of (S)-N-tert-butylsulfonyl-alpha-amido stannanes was transferred with up to 90% inversion of configuration at 100 degrees C.

  DOI：

  10.1021/jo202597p
• 作为产物：
  描述：

  二氧化碳 、 4-tolyl(tributylstannyl)methyl acetate 在 cesium fluoride 、 盐酸 作用下， 以 N,N-二甲基甲酰胺 、 乙醚 、 水 为溶剂， 60.0 ℃ 、100.0 kPa 条件下， 反应 3.0h， 生成 acetoxy-p-tolyl-acetic acid
  参考文献：
  名称：

  Synthesis of Arylglycine and Mandelic Acid Derivatives through Carboxylations of α-Amido and α-Acetoxy Stannanes with Carbon Dioxide

  摘要：

  Incorporation reactions of carbon dioxide (CO2) with N-Boc-alpha\-amido and a-acetoxy stannanes were developed using CsF as a mild tin activator. Monoprotected alpha-amido stannanes could be used, and the corresponding arylglycine derivatives were obtained in moderate-to-high yields under 1 MPa (10 atm) of CO2 pressure. alpha-Acetoxy stannanes also underwent carboxylation to afford mandelic acid derivatives in excellent yields under ambient CO2 pressure. Both transformations enabled the synthesis of alpha-tertiary and alpha-quaternary carboxylic acid derivatives. In addition, the chirality of (S)-N-tert-butylsulfonyl-alpha-amido stannanes was transferred with up to 90% inversion of configuration at 100 degrees C.

  DOI：

  10.1021/jo202597p

文献信息

• Electron-transfer processes: oxidation of arylacetic acids by peroxydisulphate in acetic acid
  作者：Claudio Giordano、Aldo Belli、Attilio Citterio、Francesco Minisci

  DOI：10.1039/p19810001574

  日期：——

  The oxidation of arylacetic acids by peroxydisulphate in acetic acid media in the presence of potassium and coppe-(II) acetates leads to the corresponding benzylacetates. The mechanism of the reaction is rationalized by the occurence of two pathways: the intermediate formation of aromatic radical cations or the direct decarboxylation of the arylacetate ion. The importance of acetic acid as a rection

  在乙酸钾和乙酸铜-（II）存在下，过乙酸在乙酸介质中被过氧二硫酸盐氧化，生成相应的乙酸苄酯。该反应的机理通过两条途径的出现而得以合理化：芳族自由基阳离子的中间形成或芳基乙酸根离子的直接脱羧。强调了乙酸作为反应介质的重要性。
• N-alkyl derivatives of 2-amino-6,7-dimethoxy tetraline, process for their preparation and pharmaceutical compositions having antihypertensive activity containing same
  申请人：SIGMA TAU Industrie Farmaceutiche Riunite S.p.A.

  公开号：EP0273017B1

  公开（公告）日：1992-09-16
• The Preparation of Substituted Mandelic Acids and their Bacteriological Effects. III
  作者：J. L. Riebsomer、Dale Stauffer、Francis Glick、Frederick Lambert

  DOI：10.1021/ja01261a021

  日期：1942.9
• US5047433A
  申请人：——

  公开号：US5047433A

  公开（公告）日：1991-09-10
• US5641475A
  申请人：——

  公开号：US5641475A

  公开（公告）日：1997-06-24