benzothiophene-5-acetic acid ethyl ester | 98820-66-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并噻吩类
• 英文名称: benzothiophene-5-acetic acid ethyl ester
• 英文别名: ethyl 2-(1-benzothiophen-5-yl)acetate；ethyl 2-(benzo[b]thiophen-5-yl)acetate
• CAS: 98820-66-7
• 化学式: C₁₂H₁₂O₂S
• 分子量: 220.292
• InChiKey: PBBOLVGWXFGFED-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  15
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  54.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  benzothiophene-5-acetic acid ethyl ester 在 亚硝酸丁酯 、 sodium ethanolate 作用下， 以 乙醇 为溶剂， 以31%的产率得到oxime of benzothiophene-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
• 作为产物：
  描述：

  (6,7-dihydro-4-hydroxybenzothien-5(4H)-ylidene)acetic acid ethyl ester 在 对甲苯磺酸 作用下， 以 甲苯 为溶剂， 反应 2.0h， 生成 benzothiophene-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

文献信息

• Copper-Catalyzed Ullmann-Type Coupling and Decarboxylation Cascade of Arylhalides with Malonates to Access α-Aryl Esters
  作者：Fei Cheng、Tao Chen、Yin-Qiu Huang、Jia-Wei Li、Chen Zhou、Xiao Xiao、Fen-Er Chen

  DOI：10.1021/acs.orglett.1c03688

  日期：2022.1.14

  We have developed a high-efficiency and practical Cu-catalyzed cross-coupling to directly construct versatile α-aryl-esters by utilizing readily available aryl bromides (or chlorides) and malonates. These gram-scale approaches occur with turnovers of up to 1560 and are smoothly conducted by the usage of a low catalyst loading, a new available ligand, and a green solvent. A variety of functional groups

  我们开发了一种高效实用的铜催化交叉偶联，通过利用容易获得的芳基溴化物（或氯化物）和丙二酸盐直接构建多功能的 α-芳基酯。这些克级方法的周转率高达 1560，并且通过使用低催化剂负载、新的可用配体和绿色溶剂顺利进行。可以耐受多种官能团，并且使用 α-芳基酯来获得克级的非甾体抗炎药 (NSAID)。
• Organic Base Enabled Nickel‐Catalyzed Mono‐α‐Arylation of Feedstock Solvents
  作者：Joshua W. M. MacMillan、Ryan T. McGuire、Mark Stradiotto

  DOI：10.1002/chem.202200764

  日期：2022.5.16

  We report on our successful development of the first metal-catalyzed mono-α-arylation of carbonyl compounds employing a soluble organic base. The scope of these Ni/DalPhos-catalyzed transformations encompasses a range of (hetero)aryl halides (Cl, Br, I) and phenol-derived electrophiles (sulfonates, carbonates, carbamates, sulfamates), including active pharmaceutical ingredients (chloroquine, clozapine)

  我们报告了我们使用可溶性有机碱成功开发了第一个金属催化的羰基化合物单α-芳基化。这些 Ni/DalPhos 催化转化的范围包括一系列（杂）芳基卤化物（Cl、Br、I）和苯酚衍生的亲电子试剂（磺酸盐、碳酸盐、氨基甲酸盐、氨基磺酸盐），包括活性药物成分（氯喹、氯氮平） ，与通常有问题的原料小分子底物丙酮、二甲基乙酰胺结合，并首次与任何金属催化剂/碱、乙酸乙酯结合。
• JP5763313
  申请人：——

  公开号：——

  公开（公告）日：——