4,5,6,7-tetrahydro-α-hydroxy-4-oxobenzothiophene-5-acetic acid ethyl ester | 98799-80-5

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 4,5,6,7-tetrahydro-α-hydroxy-4-oxobenzothiophene-5-acetic acid ethyl ester
• CAS: 98799-80-5
• 化学式: C₁₂H₁₄O₄S
• 分子量: 254.307
• InChiKey: YAEXYIAKJBHMFO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.42
• 重原子数：
  17.0
• 可旋转键数：
  3.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  63.6
• 氢给体数：
  1.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  4,5,6,7-tetrahydro-α-hydroxy-4-oxobenzothiophene-5-acetic acid ethyl ester 在 对甲苯磺酸 作用下， 以 甲苯 为溶剂， 以88%的产率得到(6,7-dihydro-4-oxobenzothiene-5(4H)-ylidene)acetic acid ethyl ester
  参考文献：
  名称：

  Orally absorbable cephalosporin antibiotics. 2. Structure-activity studies of bicyclic glycine derivatives of 7-aminodeacetoxycephalosporanic acid

  摘要：

  Three positional analogues (4-, 5-, and 7-) of benzothienylglycine and (N-acetylindolinyl)-5-glycine were prepared and coupled to 7-aminodeacetoxycephalosporanic acid (7-ADCA) to give the cephalosporins 17a-c. In addition two isomeric (2,3-b and 3,2-b) thienothiopheneglycines were synthesized and coupled to 7-ADCA to yield cephalosporins 30d and 30e. In vitro testing of these new cephalosporins indicates good activity against Gram-positive bacteria. Against Streptococcus pneumoniae infections compound 25 displayed better mouse protection (both orally and subcutaneously) than cephalexin.

  DOI：

  10.1021/jm00150a023
• 作为产物：
  描述：

  4,5,6,7-四氢-4-苯并噻吩 在 sodium tetrahydroborate 、 乙醇 、 sodium hydride 作用下， 以 乙醚 、 乙醇 为溶剂， 反应 9.0h， 生成 4,5,6,7-tetrahydro-α-hydroxy-4-oxobenzothiophene-5-acetic acid ethyl ester
  参考文献：
  名称：

  Orally absorbable cephalosporin antibiotics. 2. Structure-activity studies of bicyclic glycine derivatives of 7-aminodeacetoxycephalosporanic acid

  摘要：

  Three positional analogues (4-, 5-, and 7-) of benzothienylglycine and (N-acetylindolinyl)-5-glycine were prepared and coupled to 7-aminodeacetoxycephalosporanic acid (7-ADCA) to give the cephalosporins 17a-c. In addition two isomeric (2,3-b and 3,2-b) thienothiopheneglycines were synthesized and coupled to 7-ADCA to yield cephalosporins 30d and 30e. In vitro testing of these new cephalosporins indicates good activity against Gram-positive bacteria. Against Streptococcus pneumoniae infections compound 25 displayed better mouse protection (both orally and subcutaneously) than cephalexin.

  DOI：

  10.1021/jm00150a023