Ethyl 2-(ethylthio)benzoate | 100058-70-6

• 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: Ethyl 2-(ethylthio)benzoate
• 英文别名: 2-Aethylmercapto-benzoesaeure-aethylester；2-ethylsulfanyl-benzoic acid ethyl ester；S-Aethyl-thiosalicylsaeure-aethylester；Benzoic acid, 2-(ethylthio)-, ethyl ester；ethyl 2-ethylsulfanylbenzoate
• CAS: 100058-70-6
• 化学式: C₁₁H₁₄O₂S
• 分子量: 210.297
• InChiKey: KPBGTWGFCNKPOM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  14
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  51.6
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  Ethyl 2-(ethylthio)benzoate 在 sodium periodate 、 甲基氯化镁 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 36.83h， 生成 2-<2-(Ethylsulfinyl)benzoyl>pyrrole
  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：

  Cumarin-diethylacetal 以61%的产率得到
  参考文献：
  名称：

  SATO KOZO; NAGAMORI YUKITO; OKAZAKI MITSUO, NIXON KAGAKU KAJSI, NIRRON KAGAKU KAISNI , J. CHEM. SOS. JAR., C+

  摘要：

  DOI：

文献信息

• New Thiosemicarbazides and 1,2,4-Triazolethiones Derived from 2-(Ethylsulfanyl) Benzohydrazide as Potent Antioxidants
  作者：Nafal Nazarbahjat、Nurdiana Nordin、Zanariah Abdullah、Mahmood Abdulla、Wageeh Yehye、Siti Halim、Chin Kee、Azhar Ariffin

  DOI：10.3390/molecules190811520

  日期：——

  New thiosemicarbazide derivatives 2–6 were synthesised by reacting 2-(ethylsulfanyl)benzohydrazide with various aryl isothiocyanates. The cyclisation of compounds 2–6 under reflux conditions in a basic medium (aqueous NaOH, 4 N) yielded compounds 7–11 that contain a 1,2,4-triazole ring. All of the synthesised compounds were screened for their antioxidant activities. Compounds 2, 3, and 7 showed better radical scavenging in a 2,2-diphenyl-1-picrylhydrazyl (DPPH) assay, with IC50 values of 1.08, 0.22, and 0.74 µg/mL, respectively, compared to gallic acid (IC50, 1.2 µg/mL). Compound 3 also showed superior results in a ferric reducing antioxidant power (FRAP) assay (3054 µM/100 g) compared to those of ascorbic acid (1207 µM/100 g).

  新型硫代氨基脲衍生物2-6是通过将2-(乙基硫基)苯腙与各种芳基异硫氰酸酯反应合成的。在基本介质（4 N NaOH水溶液）中，化合物2-6经回流反应环化得到含有1,2,4-三唑环的化合物7-11。所有合成的化合物均进行了抗氧化活性筛选。化合物2、3和7在2,2-二苯基-1-苦味腙（DPPH）实验中显示出更好的自由基清除能力，其IC50值分别为1.08、0.22和0.74 µg/mL，相比于没食子酸（IC50为1.2 µg/mL）。化合物3在铁还原抗氧化能力（FRAP）实验中也显示出优越的结果（3054 µM/100 g），而抗坏血酸的结果为1207 µM/100 g。
• Pyrrolo(1,2-b)-(1,2)-benzothiazin-10-one and its use as an antimicrobial
  申请人：The Dow Chemical Company

  公开号：US05270307A1

  公开（公告）日：1993-12-14

  Pyrrolo-(1,2-b)-(1,2)-benzothiazin-10-one is prepared which corresponds to the formula: ##STR1## This compound has been found to exhibit antimicrobial activity in industrial and commercial applications and compositions containing this compound are so employed.

  制备了对应于以下式子的吡咯-(1,2-b)-(1,2)-苯并噻唑-10-酮：##STR1## 发现该化合物在工业和商业应用中表现出抗微生物活性，并且含有该化合物的组合物被应用于此类用途。
• Transition-Metal-Free Dehydrogenative Cyclization via α-Csp3–H Activation of Ethers and Thioethers
  作者：Ranjan Jana、Kartic Manna、Hasina Mamataj Begam

  DOI：10.1055/a-2017-6065

  日期：——

  S-alkylated salicylic or thiosalicylic acid derivatives to access 4H-benzo[d][1,3]dioxin-4-ones or 4H-benzo[d][1,3]oxathiin-4-ones, respectively. The oxidative cyclization of salicylic acid derivatives proceeds through a radical pathway at 110 °C. In contrast, the cyclization of the thiosalicylic acids proceeds smoothly at room temperature via an ionic pathway. Notably, the overall reactions are fast, completed

  我们在此报道了四乙基溴化铵催化 O- 或 S- 烷基化水杨酸或硫代水杨酸衍生物的分子内氧化环化以获得 4 H -苯并[ d ] [1,3] 二恶英-4-酮或 4 H -苯并[ d ] [ 1,3]oxathiin-4-ones，分别。水杨酸衍生物的氧化环化在 110 °C 通过自由基途径进行。相反，硫代水杨酸的环化在室温下通过离子途径顺利进行。值得注意的是，整体反应速度快，反应时间短，产品收率高，季碳中心形成顺利。
• Brand; Stein, Journal fur praktische Chemie (Leipzig 1954), 1924, vol. <2> 108, p. 25
  作者：Brand、Stein

  DOI：——

  日期：——
• Bonnema,J.; Arens,J.F., Recueil des Travaux Chimiques des Pays-Bas, 1960, vol. 79, p. 1137 - 1149
  作者：Bonnema,J.、Arens,J.F.

  DOI：——

  日期：——