1-((2-bromophenyl)thio)propan-2-one | 17514-55-5

• 分子结构分类: 有机化合物 - 有机硫化合物 - 硫醚类
• 英文名称: 1-((2-bromophenyl)thio)propan-2-one
• 英文别名: 1-[(2-Bromophenyl)sulfanyl]propan-2-one；1-(2-bromophenyl)sulfanylpropan-2-one
• CAS: 17514-55-5
• 化学式: C₉H₉BrOS
• mdl: MFCD12147360
• 分子量: 245.14
• InChiKey: GYJCNXHTLAJBCT-UHFFFAOYSA-N

物化性质

• 沸点：
  161-162 °C(Press: 5 Torr)
• 密度：
  1.49±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  12
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.222
• 拓扑面积：
  42.4
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  1-((2-bromophenyl)thio)propan-2-one 在 正丁基锂 、 四甲基乙二胺 作用下， 以 四氢呋喃 、 乙醚 、 正戊烷 为溶剂， 生成 3-methyl-7-(ethylglyoxyl)benzothiophene
  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：

  2-溴硫代苯酚 、 一氯丙酮 在 potassium carbonate 作用下， 以 丙酮 为溶剂， 反应 12.0h， 以86%的产率得到1-((2-bromophenyl)thio)propan-2-one
  参考文献：
  名称：

  用于通过酮还原酶在 C-O 或 C-S 键处具有立体中心的 β-羟基硫化物的对映选择性合成的化学酶级联反应

  摘要：

  鉴定了四种酮还原酶 (KRED) 用于 β-羟基硫化物的对映选择性合成。KRED311 和 KRED349 通过苯硫酚/硫醇和 α-卤代酮/醇的化学酶级联催化合成在 C-O 键处具有立体中心且绝对构型相反的 β-羟基硫化物。KRED253 和 KRED384 通过外消旋 α-硫代醛的动态动力学拆分 (DKR) 催化合成在 C-S 键处具有立体中心并具有相反对映选择性的 β-羟基硫化物。

  DOI：

  10.1002/anie.202202363

文献信息

• α-Arylchalcogenation of acetone with diaryl dichalcogenide via metal-free oxidative C(sp3)–H bond functionalization
  作者：Guobing Yan、Arun Jyoti Borah、Lianggui Wang、Zhangjin Pan、Shuangshuang Chen、Xuqian Shen、Xiangmei Wu

  DOI：10.1016/j.tetlet.2015.05.059

  日期：2015.7

  Direct α-arylchalcogenation of acetone with diaryl dichalcogenides has been achieved by using a mixture of TBHP and DTBP oxidants at 120 °C without transition-metal catalyst via oxidative C(sp3)–H bond functionalization. The method exhibits good functional group tolerance and products were isolated in moderate to high yields.

  通过在120°C下使用TBHP和DTBP氧化剂的混合物，而无过渡金属催化剂通过C（sp3）–H键的氧化作用，可实现丙酮与二芳基二卤代丙酮的直接α-芳基硫醇化。该方法表现出良好的官能团耐受性，并且以中等至高收率分离出产物。
• Benzylamine derivatives, their preparation and their application in
  申请人：Synthelabo

  公开号：US06060508A1

  公开（公告）日：2000-05-09

  Compounds of general formula (I) ##STR1## in which: A represents either a hydrogen atom, a hydroxyl, a C.sub.1-6 hydroxyalkyl group, a thiol, a C.sub.1-6 alkylsulphanyl group, an amino group, a C.sub.1-6 alkylamino group, a di(C.sub.1-6 alkyl)amino group, a C.sub.1-6 alkylhydroxylamine group, a C.sub.1-6 alkoxy group, a hydroxylamine group, an N,O-di(C.sub.1-6 alkyl)hydroxylamine group, an azido or a halogen such as fluorine, chlorine or bromine, B represents a hydrogen atom, a linear or branched C.sub.1-6 alkyl group, a C.sub.2-6 alkenyl group, a C.sub.1-6 fluoroalkyl group, a C.sub.1-2 perfluoroalkyl group, a C.sub.1-6 alkoxy group, a phenyl group or an oxo group, X represents an oxygen or sulphur atom. Application in therapeutics.

  通式为（I）##STR1##的化合物，其中：A代表氢原子，羟基，C.sub.1-6羟基烷基，硫醇，C.sub.1-6烷基硫基，氨基，C.sub.1-6烷基氨基，二（C.sub.1-6烷基）氨基，C.sub.1-6烷基羟肟基，C.sub.1-6烷氧基，羟肟基，N，O-二（C.sub.1-6烷基）羟肟基，偶氮基或氟、氯或溴等卤素；B代表氢原子，线性或支链C.sub.1-6烷基，C.sub.2-6烯基，C.sub.1-6氟烷基，C.sub.1-2全氟烷基，C.sub.1-6烷氧基，苯基或氧代基；X代表氧或硫原子。在治疗方面的应用。
• FabI酶抑制剂及其制备方法和应用
  申请人：广州白云山医药集团股份有限公司白云山制药总厂

  公开号：CN117886805A

  公开（公告）日：2024-04-16

  本发明提供FabI酶抑制剂及其制备方法和应用，所述FabI酶抑制剂具有如式I所示的化合物，本发明化合物具有良好的FabI酶抑制活性，对耐药菌以及敏感金葡菌具有明显抑菌作用。#imgabs0#
• [EN] alpha -AZACYCLOMETHYL BENZOTHIOPHENE AND alpha -AZACYCLOMETHYL BENZOFURANE DERIVATIVES, PREPARATION AND THERAPEUTIC APPLICATION<br/>[FR] DERIVES DE alpha -AZACYCLOMETHYL BENZOTHIOPHENE ET DE alpha -AZACYCLOMETHYL BENZOFURANE, LEUR PREPARATION ET LEUR APPLICATION EN THERAPEUTIQUE
  申请人：SANOFI-SYNTHELABO

  公开号：WO1998033793A1

  公开（公告）日：1998-08-06

  (EN) The invention concerns compounds of formula (I) in which A represents either a hydrogen atom or a hydroxyl group, R1, R2, R4, identical or different, each represent a hydrogen atom, a halogen such as fluorine, chlorine or bromine, a cyano group, a C1-6 alkyl group, a C2-6 alkenyl group, a C3-6 cycloalkyl group, a C3-6 cycloalkenyl group, a C6-14 aryl, a C1-6 alcoxycarbonyl group, a C1-6 hydroxyalkyl group, a C1-6 alcoxy group, a C1-6 alcoxyalkyl group, a C1-6 fluoroalkyl group, a C1-2 perfluoroalkyl group, or R1 and R2 together form, with the benzothiophene or benzofurane carbons bearing R1 and R2, a phenyl; R3 represents a hydrogen atom, a C1-6 alkyl group, a C2-6 alkenyl group, a C1-6 fluoroalkyl group, a C1-2 perfluoroalkyl group, C3-6 cycloalkyl group, C3-6 cycloalkenyl group, a phenyl or a benzyl, a C1-6 alcoxycarbonyl group; R5 represents a hydrogen atom or a halogen such as fluorine, chlorine or bromine; and n represents a whole number from 1 to 6. The invention is applicable in therapy.(FR) Composés de formule (I) dans laquelle: A représente soit un atome d'hydrogène, soit un groupe hydroxyle; R1, R2, R4, identiques ou différents, représentent chacun un atome d'hydrogène, un halogène tel que le fluor, le chlore ou le brome, un groupe cyano, un groupe C1-6 alkyle, un groupe C2-6 alkényle, un groupe C3-6 cycloalkyle, un groupe C3-6 cycloalkényle, un aryle en C6-14, un groupe C1-6 alcoxycarbonyle, un groupe C1-6 hydroxyalkyle, un groupe C1-6 alcoxy, un groupe C1-6 alcoxyalkyle, un groupe C1-6 fluoroalkyle, un groupe C1-2 perfluoroalkyle, ou R1 et R2 forment ensemble une chaîne C1-6 alkylène, une chaîne C3-6 alkénylène, ou R1 et R2 forment ensemble, avec les carbones du benzothiophène ou du benzofurane portant R1 et R2, un phényle; R3 représente un atome d'hydrogène, un groupe C1-6 alkyle, un groupe C2-6 alkényle, un groupe C1-6 fluoroalkyle, un groupe C1-2 perfluoroalkyle, C3-6 cycloalkyle, C3-6 cycloalkényle, un phényle ou un benzyle, un groupe C1-6 alcoxycarbonyle; R5 représente un atome d'hydrogène ou un halogène tel que le fluor, le chlore ou le brome, et n représente un nombre entier de 1 à 6. Application en thérapeutique.
• Orally absorbable cephalosporin antibiotics. 2. Structure-activity studies of bicyclic glycine derivatives of 7-aminodeacetoxycephalosporanic acid
  作者：Stjepan Kukolja、Susan E. Draheim、Bernard J. Graves、David C. Hunden、Janice L. Pfeil、Robin D. G. Cooper、John L. Ott、Fred T. Counter

  DOI：10.1021/jm00150a023

  日期：1985.12

  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.