2-ethylsulfanyl benzoic acid chloride | 173312-15-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 2-ethylsulfanyl benzoic acid chloride
• 英文别名: 2-ethylsulfanyl-benzoyl chloride；2-Aethylmercapto-benzoylchlorid；2-Aethylmercapto-benzoesaeure-chlorid；2-(ethylthio)benzoyl chloride；2-ethylsulfanylbenzoyl chloride
• CAS: 173312-15-7
• 化学式: C₉H₉ClOS
• 分子量: 200.689
• InChiKey: PRFYPNGSTNJXQV-UHFFFAOYSA-N

物化性质

• 沸点：
  283.4±23.0 °C(Predicted)
• 密度：
  1.24±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  12
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.22
• 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：

  2-ethylsulfanyl benzoic acid chloride 在 sodium hydroxide 、 sodium periodate 、 三氯化铝 、 四丁基氟化铵 、 四丁基硫酸氢铵 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 、 xylene 、 苯 为溶剂， 反应 13.75h， 生成 1-methyl-4H-<1>benzothiopyrano<2,3-b>pyrrol-4-one
  参考文献：
  名称：

  Sulfenylation Using Sulfoxides. Intramolecular Cyclization of 2- and 3-Acylpyrroles

  摘要：

  AlCl3-catalyzed acylation of N-(phenylsulfonyl)pyrrole with 2-(ethylthio)benzoyl chloride followed by hydrolysis provided 2-(2-(ethylthio)benzoyl)pyrrole (3). Compound 3 was also available from ethyl 2-(ethylthio)benzoate and pyrrolylmagnesium chloride (Scheme 2). Oxidation(NaIO4) gave the corresponding sulfoxide 4 which when refluxed 6 h inp-xylene (bp 138 degrees C) gave predominately the C-3 cyclization product 11 (51%) along with the rearrangement product 12 (17%). Conducting the thermal reaction in the presence of DMAP in refluxing toluene gave mainly the N-1 cyclization product 13 (46%) also accompanied by the rearrangement product 12 (20%). Formation of a 2H-pyrrole spirocyclic intermediate from thermally promoted intramolecular ipso-sulfenylation in 4 is suggested to account for the formation of 12. The N-methyl derivative of 4 (i.e. 6) produced 9 and 10 after 9 h at 138 degrees C; in the presence of DMAP only 9 is produced after 18 h at 138 degrees C. The 3-acyl sulfoxide 8 cyclized to 17 during 6.5 h at 138 degrees C. These results indicate that although sulfoxides are useful for intramolecular sulfenylation reactions, care must be taken in assigning structures to the product(s) because rearrangement may take place during and/or after the initial cyclization reaction. Addition of a basic amine to the reaction mixture may prevent acid-catalyzed rearrangements of the initially formed products.

  DOI：

  10.1021/jo00105a026
• 作为产物：
  描述：

  邻氨基苯甲酸 在 盐酸 、 五氯化磷 、 sodium nitrite 作用下， 生成 2-ethylsulfanyl benzoic acid chloride
  参考文献：
  名称：

  The Synthesis of Some Alkamine Esters of Alkylthiobenzoic Acids

  摘要：

  DOI：

  10.1021/ja01858a063

文献信息

• [EN] DIARYLTRIAZOLES AS INHIBITORS OF 11-BETA-HYDROXYSTEROID DEHYDROGENASE-1<br/>[FR] UTILISATION DE DIARYLTRIAZOLES COMME INHIBITEURS DE LA 11-BETA-HYDROXYSTEROIDE DESHYDROGENASE-1
  申请人：MERCK & CO INC

  公开号：WO2005097759A1

  公开（公告）日：2005-10-20

  2,5-Diaryl-1,2,4-triazole derivatives of structural formula I are selective inhibitors of the 11β-hydroxysteroid dehydrogenase Type 1 enzyme (11β-HSD-1). The compounds are useful for the treatment of diabetes, hyperglycemia, obesity, insulin resistance, atherosclerosis, dyslipidemia, hyperlipidemia, hypertension, and Metabolic Syndrome. Also disclosed are novel compounds of structural formula II which are inhibitors of 11β-HSD-1.

  2,5-二芳基-1,2,4-三唑衍生物的结构式I是11β-羟基类固醇脱氢酶1型酶（11β-HSD-1）的选择性抑制剂。这些化合物用于治疗糖尿病、高血糖、肥胖、胰岛素抵抗、动脉硬化、血脂异常、高血脂、高血压和代谢综合征。还公开了结构式II的新化合物，它们是11β-HSD-1的抑制剂。
• [EN] FUSED HETEROCYCLIC COMPOUND AND USE FOR PEST CONTROL THEREOF<br/>[FR] COMPOSÉ HÉTÉROCYCLIQUE FUSIONNÉ ET SON UTILISATION POUR LA LUTTE CONTRE LES RAVAGEURS
  申请人：SUMITOMO CHEMICAL CO

  公开号：WO2012086848A1

  公开（公告）日：2012-06-28

  A fused heterocyclic compound the formula (1) : wherein A1 represents -NR8-, and the like; A2 represents a nitrogen atom, and the like; A3 represents a nitrogen atom, and the like; R1 represents a C1-C6 chain hydrocarbon group optionally having one or more atoms or groups selected from Group X, and the like; R2, R3, R4, and R5 are same or different and represent independently a C1-C6 chain hydrocarbon group optionally having one or more halogen atoms, and the like; R6 and R7 are same or different and represent independently a C1-C6 chain hydrocarbon group optionally having one or more atoms or groups selected from Group X, and the like; R8 represents a C1-C6 chain hydrocarbon group optionally having one or more atoms or groups selected from Group W, and the like; n represents 0, 1 or 2. The compound has an excellent activity of controlling pests.

  一种融合的杂环化合物，其化学式（1）：其中A1代表-NR8-等；A2代表一个氮原子等；A3代表一个氮原子等；R1代表一个C1-C6链烃基，可选地具有来自X组的一个或多个原子或基团等；R2、R3、R4和R5相同或不同，独立地代表一个C1-C6链烃基，可选地具有一个或多个卤素原子等；R6和R7相同或不同，独立地代表一个C1-C6链烃基，可选地具有来自X组的一个或多个原子或基团等；R8代表一个C1-C6链烃基，可选地具有来自W组的一个或多个原子或基团等；n代表0、1或2。该化合物具有优异的控制害虫活性。
• Synthesis, spectral characterization and electrochemical properties of (2-alkylthiobenzoyl)ferrocenes. Crystal structures of 2-methylthio, 2-ethylthio and 2-isopropylthio derivatives
  作者：Zoran Ratković、Slađana B. Novaković、Goran A. Bogdanović、Dejan Šegan、Rastko D. Vukićević

  DOI：10.1016/j.poly.2010.04.034

  日期：2010.7

  (2-alkylthiobenzoyl)ferrocenes has been achieved by Friedel–Crafts acylation of ferrocene with acid chlorides generated in situ from the corresponding carboxylic acids and phosphorous trichloride. The obtained compounds were characterized by spectroscopic data (UV, IR, 1H and 13C NMR), whereas their electrochemical properties have been investigated by cyclic voltammetry. The single-crystal X-ray structure determinations

  一锅法合成了七种新的（2-烷基硫代苯甲酰基）二茂铁，这是通过将二茂铁与相应的羧酸和三氯化磷原位生成的酰氯进行Friedel-Crafts酰化反应而实现的。所得化合物通过光谱数据（UV，IR，1 H和13NMR），而其电化学性质已通过循环伏安法研究。还报告了其中三个的单晶X射线结构测定。这三种衍生物均表现出分子内C–H…O相互作用，其中涉及环戊二烯基（Cp）环的供体和羰基氧作为受体。这种相互作用有利于两个部分的共面排列。符合C–O键的向量与相应的Cp平面之间的夹角均小于6.4°。常规的氢键在这三个晶体结构中都不存在，但是已经发现并详细分析了某些类型的C–H…O，C–H…S和C–H…π类型的弱分子间相互作用。
• Diaryltriazoles as Inhibitors of 11-Beta-Hydroxysteroid Dehydrogenase-1
  申请人：Aster Susan D.

  公开号：US20080255216A1

  公开（公告）日：2008-10-16

  2,5-Diaryl-1,2,4-triazole derivatives of structural formula I are selective inhibitors of the 11&bgr;-hydroxysteroid dehydrogenase Type 1 enzyme (11&bgr;-HSD-1). The compounds are useful for the treatment of diabetes, hyperglycemia, obesity, insulin resistance, atherosclerosis, dyslipidemia, hyperlipidemia, hypertension, and Metabolic Syndrome. Also disclosed are novel compounds of structural formula II which are inhibitors of 11&bgr;-HSD-1.

  结构式为I的2,5-二芳基-1,2,4-三唑衍生物是11β-羟类固醇脱氢酶1型酶（11β-HSD-1）的选择性抑制剂。这些化合物可用于治疗糖尿病、高血糖、肥胖症、胰岛素抵抗、动脉硬化、血脂异常、高脂血症、高血压和代谢综合征。还披露了结构式II的新化合物，它们是11β-HSD-1的抑制剂。
• Diaryltriazoles as inhibitors of 11-beta-hydroxysteroid dehydrogenase-1
  申请人：Merck Sharp & Dohme Corp.

  公开号：US08178546B2

  公开（公告）日：2012-05-15

  2,5-Diaryl-1,2,4-triazole derivatives of structural formula I are selective inhibitors of the 11β-hydroxysteroid dehydrogenase Type 1 enzyme (11β-HSD-1). The compounds are useful for the treatment of diabetes, hyperglycemia, obesity, insulin resistance, atherosclerosis, dyslipidemia, hyperlipidemia, hypertension, and Metabolic Syndrome. Also disclosed are novel compounds of structural formula II which are inhibitors of 11β-HSD-1.

  结构式I中的2,5-二芳基-1,2,4-三唑衍生物是11β-羟基类固醇脱氢酶1型酶（11β-HSD-1）的选择性抑制剂。这些化合物可用于治疗糖尿病、高血糖、肥胖症、胰岛素抵抗、动脉粥样硬化、血脂异常、高脂血症、高血压和代谢综合征。此外，还披露了结构式II的新化合物，它们是11β-HSD-1的抑制剂。