tert-butyl 2-hydroxy-3-methylbenzoate | 221646-18-0

• 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: tert-butyl 2-hydroxy-3-methylbenzoate
• CAS: 221646-18-0
• 化学式: C₁₂H₁₆O₃
• 分子量: 208.257
• InChiKey: RZOCQXKVGCNXBC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.2
• 重原子数：
  15
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  46.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  tert-butyl 2-hydroxy-3-methylbenzoate 在 4-二甲氨基吡啶 、 N-溴代丁二酰亚胺(NBS) 、 三乙胺 作用下， 以 四氯化碳 、 二氯甲烷 为溶剂， 生成 2-Acetoxy-3-bromomethyl-benzoic acid tert-butyl ester
  参考文献：
  名称：

  “头孢菌素样”环状双肽：与β-内酰胺识别酶的合成和反应。

  摘要：

  已合成了环状二烯肽8-羧基-3-苯基乙酰胺基-3,4-二氢-2H-1-苯并吡喃-2-酮（一种与头孢菌素具有结构相似性的芳基苯乙酸酯的环状类似物），作为B的潜在底物/抑制剂-内酰胺识别酶。发现它是紧密结合的，A类β-内酰胺酶的弱底物和几种DD-肽酶的不可逆抑制剂。

  DOI：

  10.1016/s0960-894x(98)00739-2
• 作为产物：
  描述：

  3-甲基水杨酸 、 N,N-二甲基甲酰胺二叔丁基缩醛 以 四氢呋喃 为溶剂， 生成 tert-butyl 2-hydroxy-3-methylbenzoate
  参考文献：
  名称：

  “头孢菌素样”环状双肽：与β-内酰胺识别酶的合成和反应。

  摘要：

  已合成了环状二烯肽8-羧基-3-苯基乙酰胺基-3,4-二氢-2H-1-苯并吡喃-2-酮（一种与头孢菌素具有结构相似性的芳基苯乙酸酯的环状类似物），作为B的潜在底物/抑制剂-内酰胺识别酶。发现它是紧密结合的，A类β-内酰胺酶的弱底物和几种DD-肽酶的不可逆抑制剂。

  DOI：

  10.1016/s0960-894x(98)00739-2

文献信息

• Microwave-Assisted Ester Formation Using <i>O</i>-Alkylisoureas: A Convenient Method for the Synthesis of Esters with Inversion of Configuration
  作者：Alessandra Chighine、Stefano Crosignani、Marie-Claire Arnal、Mark Bradley、Bruno Linclau

  DOI：10.1021/jo900476y

  日期：2009.7.3

  The formation of carboxylic esters via reaction of carboxylic acids with O-alkylisoureas proceeds in excellent yields with very short reaction times when conducted in a monomode microwave synthesizer. Efficient processes were developed using preformed or commercially available isoureas derived from primary and secondary alcohols, with a reaction time of only 5 min or less. It was demonstrated that under these microwave conditions, ester formation proceeded in good yields with clean inversion of configuration where appropriate. The process was validated using menthol, a hindered substrate for S(N)2 reactions. In addition, starting from primary alcohols, ester formation was successfully accomplished using ail in situ isourea formation procedure. A polymer-assisted solution-phase procedure was also developed by employing preformed solid-supported isoureas and by an efficient "catch and release" ester formation procedure whereby primary alcohols were caught on resin as isoureas by reaction with immobilized carbodiimide and released as esters by subsequent treatment with a carboxylic acids.
• A “cephalosporin-like” cyclic depsipeptide: Synthesis and reaction with ß-lactam-recognizing enzymes
  作者：S.A Adediran、D Cabaret、R.F Pratt、M Wakselman

  DOI：10.1016/s0960-894x(98)00739-2

  日期：1999.2

  8-carboxy-3-phenylacetamido-3,4-dihydro-2H-1-benzopyran-2-one, a cyclic analog of aryl phenaceturates with structural similarity to cephalosporins, has been synthesized as a potential substrate/inhibitor of B-lactam-recognizing enzymes. It was found to be a tight-binding, poor substrate of class A beta-lactamases and an irreversible inhibitor of several DD-peptidases.

  已合成了环状二烯肽8-羧基-3-苯基乙酰胺基-3,4-二氢-2H-1-苯并吡喃-2-酮（一种与头孢菌素具有结构相似性的芳基苯乙酸酯的环状类似物），作为B的潜在底物/抑制剂-内酰胺识别酶。发现它是紧密结合的，A类β-内酰胺酶的弱底物和几种DD-肽酶的不可逆抑制剂。