2-Acetyloxy-2-(2-methoxyphenyl)acetic acid | 108447-52-5

• 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: 2-Acetyloxy-2-(2-methoxyphenyl)acetic acid
• CAS: 108447-52-5
• 化学式: C₁₁H₁₂O₅
• 分子量: 224.213
• InChiKey: SWBANHHWHPBPOJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  16
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  72.8
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  2-Acetyloxy-2-(2-methoxyphenyl)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-(2-methoxyphenyl)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 、 2-methoxyphenyl(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 2-Acetyloxy-2-(2-methoxyphenyl)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

• ——
  作者：LERCH U.、 HENNING R.、 KAISER J.

  DOI：——

  日期：——
• Indolinonderivate, Verfahren zu ihrer Herstellung, sie enthaltende Arzneimittel und deren Verwendung
  申请人：HOECHST AKTIENGESELLSCHAFT

  公开号：EP0212481B1

  公开（公告）日：1990-09-12
• US4882329A
  申请人：——

  公开号：US4882329A

  公开（公告）日：1989-11-21
• Synthesis of Arylglycine and Mandelic Acid Derivatives through Carboxylations of α-Amido and α-Acetoxy Stannanes with Carbon Dioxide
  作者：Tsuyoshi Mita、Masumi Sugawara、Hiroyuki Hasegawa、Yoshihiro Sato

  DOI：10.1021/jo202597p

  日期：2012.3.2

  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.