4-(α-acetoxyacetyl)benzoic acid Ethyl Ester

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 4-(α-acetoxyacetyl)benzoic acid Ethyl Ester
• 英文别名: ethyl 4-(2-acetoxyacetyl)benzoate；ethyl 4-(2-acetyloxyacetyl)benzoate
• 化学式: C₁₃H₁₄O₅
• 分子量: 250.251
• InChiKey: UJBCVWGHAIUYNL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  18
• 可旋转键数：
  7
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  69.7
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  4-(α-acetoxyacetyl)benzoic acid Ethyl Ester 在 盐酸 、 水 作用下， 以 甲醇 为溶剂， 以85%的产率得到4-(α-hydroxyacetyl)benzoic acid ethyl ester
  参考文献：
  名称：

  Synthesis of α-Hydroxyacetophenones

  摘要：

  A general method for the preparation of alpha-hydroxyacetophenones is presented. Functionalized arylmagnesium species are transmetalated to the corresponding arylzinc intermediates, which undergo Cu(I)-catalyzed reaction with acetoxyacetyl chloride. Acidic hydrolysis of the acetate group releases the target alpha-hydroxyacetophenones with minimal production of undesired polymeric degradates that are often observed under alternative conditions.

  DOI：

  10.1021/jo3005556
• 作为产物：
  描述：

  对碘苯甲酸乙酯 、 乙酰氧基乙酰氯 在 异丙基氯化镁 、 zinc(II) chloride 、 copper(l) chloride 作用下， 以 四氢呋喃 为溶剂， 反应 1.17h， 以63%的产率得到4-(α-acetoxyacetyl)benzoic acid Ethyl Ester
  参考文献：
  名称：

  Synthesis of α-Hydroxyacetophenones

  摘要：

  A general method for the preparation of alpha-hydroxyacetophenones is presented. Functionalized arylmagnesium species are transmetalated to the corresponding arylzinc intermediates, which undergo Cu(I)-catalyzed reaction with acetoxyacetyl chloride. Acidic hydrolysis of the acetate group releases the target alpha-hydroxyacetophenones with minimal production of undesired polymeric degradates that are often observed under alternative conditions.

  DOI：

  10.1021/jo3005556

文献信息

• Synthesis and Biological Evaluation of Quinoline Salicylic Acids As P-Selectin Antagonists
  作者：Neelu Kaila、Kristin Janz、Silvano DeBernardo、Patricia W. Bedard、Raymond T. Camphausen、Steve Tam、Desirée H. H. Tsao、James C. Keith、Cheryl Nickerson-Nutter、Adam Shilling、Ruth Young-Sciame、Qin Wang

  DOI：10.1021/jm0602256

  日期：2007.1.1

  junctions into the underlying tissue. The initial rolling step is mediated by the interaction of leukocyte glycoproteins containing active moieties such as sialyl Lewisx (sLex) with P-selectin expressed on endothelial cells. Consequently, inhibition of this interaction by means of a small molecule P-selectin antagonist is an attractive strategy for the treatment of inflammatory diseases such as arthritis

  白细胞炎症和组织损伤部位的募集涉及白细胞沿内皮壁滚动，然后白细胞牢固粘附，最后白细胞跨细胞连接转运到下面的组织中。初始滚动步骤由包含活性部分的白细胞糖蛋白（如唾液酸化的Lewisx（sLex））与在内皮细胞上表达的P-选择蛋白的相互作用介导。因此，借助于小分子P-选择蛋白拮抗剂抑制这种相互作用是治疗炎性疾病如关节炎的有吸引力的策略。惠氏化学文库的高通量筛选确定了喹啉水杨酸类化合物（1）作为P-选择素的拮抗剂，其体外和基于细胞的测定方法的功效远远优于sLex。通过迭代药物化学，我们鉴定出具有改善的P-选择素活性，减少的二氢Orate脱氢酶抑制作用和可接受的CYP谱的类似物。铅化合物36在类风湿关节炎的大鼠AIA模型中有效。
• Synthesis of α-Hydroxyacetophenones
  作者：Mark McLaughlin、Kevin M. Belyk、Gang Qian、Robert A. Reamer、Cheng-yi Chen

  DOI：10.1021/jo3005556

  日期：2012.6.1

  A general method for the preparation of alpha-hydroxyacetophenones is presented. Functionalized arylmagnesium species are transmetalated to the corresponding arylzinc intermediates, which undergo Cu(I)-catalyzed reaction with acetoxyacetyl chloride. Acidic hydrolysis of the acetate group releases the target alpha-hydroxyacetophenones with minimal production of undesired polymeric degradates that are often observed under alternative conditions.