tert-butyl 2-(3-chloro-4,5-dihydroxybenzoyl)acetate | 141613-45-8

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: tert-butyl 2-(3-chloro-4,5-dihydroxybenzoyl)acetate
• 英文别名: tert-butyl 3-(3-chloro-4,5-dihydroxyphenyl)-3-oxopropanoate
• CAS: 141613-45-8
• 化学式: C₁₃H₁₅ClO₅
• 分子量: 286.712
• InChiKey: FJXCXQYZJFIRSA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.67
• 重原子数：
  19.0
• 可旋转键数：
  3.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  83.83
• 氢给体数：
  2.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  tert-butyl 2-(3-chloro-4,5-dihydroxybenzoyl)acetate 在 三氟化硼乙醚 、 水 作用下， 以 环丁砜 为溶剂， 反应 16.0h， 生成 7-amino-3-<3-(3-chloro-4,5-dihydroxyphenl)-3-oxopropyl>ceph-3-em-4-carboxylic acid
  参考文献：
  名称：

  Synthesis and structure-activity relationships of cephalosporins with C-3' catechol-containing residues

  摘要：

  Cephalosporins with new catechol substituents at C-3' have been synthesized, including novel compounds with C-3' carbon-carbon bonds. Many of these compounds have high potency against Gram-negative bacteria, in particular against resistant strains like Pseudomonas aeruginosa. Structure-activity relationships are discussed in terms of their dependence on the pK(a) of the C-3' catechol and also in terms of steric and conformational factors of the C-3' substituent. The best overall properties were found in compounds with a bulky and/or conformationally restricted acidic C-3' catechol.

  DOI：

  10.1021/jm00092a014
• 作为产物：
  描述：

  3-氯-4,5-二羟基苯甲酸 在 氯化亚砜 、 TEA 、 sodium acetate 、 sodium hydride 作用下， 以 叔丁醇 为溶剂， 生成 tert-butyl 2-(3-chloro-4,5-dihydroxybenzoyl)acetate
  参考文献：
  名称：

  Synthesis and structure-activity relationships of cephalosporins with C-3' catechol-containing residues

  摘要：

  Cephalosporins with new catechol substituents at C-3' have been synthesized, including novel compounds with C-3' carbon-carbon bonds. Many of these compounds have high potency against Gram-negative bacteria, in particular against resistant strains like Pseudomonas aeruginosa. Structure-activity relationships are discussed in terms of their dependence on the pK(a) of the C-3' catechol and also in terms of steric and conformational factors of the C-3' substituent. The best overall properties were found in compounds with a bulky and/or conformationally restricted acidic C-3' catechol.

  DOI：

  10.1021/jm00092a014