ethyl 2-(benzylthio)benzoate | 92737-52-5

• 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-(benzylthio)benzoate
• 英文别名: ethyl 2-benzylthiobenzoate；2-benzylsulfanyl-benzoic acid ethyl ester；2-Benzylmercapto-benzoesaeure-aethylester；Ethyl-(benzylthio)benzoat；Ethyl 2-benzylsulfanylbenzoate
• CAS: 92737-52-5
• 化学式: C₁₆H₁₆O₂S
• 分子量: 272.368
• InChiKey: YZGKBTCTSMYUCM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.1
• 重原子数：
  19
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.19
• 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-(benzylthio)benzoate 在 sodium tetrahydroborate 、 N,N-二甲基苯胺 、 zinc(II) chloride 作用下， 以 四氢呋喃 为溶剂， 反应 2.0h， 以98%的产率得到2-(phenylmethylthio)benzenemethanol
  参考文献：
  名称：

  在叔胺存在下用硼氢化钠和氯化锌还原某些羧酸酯的新方法

  摘要：

  在叔胺的存在下，硼氢化钠 (NaBH4) 与氯化锌 (ZnCl2) 结合显示出强大的还原性能，羧酸酯被顺利还原成它们的对应物。

  DOI：

  10.1246/bcsj.64.2730
• 作为产物：
  描述：

  2-苄基磺酰基苯羧酸 在 氯化亚砜 作用下， 生成 ethyl 2-(benzylthio)benzoate
  参考文献：
  名称：

  5-邻巯基苯基-3-甲基-1-苯基吡唑的衍生物

  摘要：

  DOI：

  10.1039/jr9540000138

文献信息

• 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。
• A Highly Efficient Cu-Catalyzed S-Transfer Reaction: From Amine to Sulfide
  作者：Yiming Li、Jiahua Pu、Xuefeng Jiang

  DOI：10.1021/ol5009747

  日期：2014.5.16

  A highly efficient Cu-catalyzed dual C-S bonds formation reaction, proceeding in alcohol and water under air, is reported, in which inodorous stable Na2S2O3 is used as a sulfurating reagent. This powerful strategy provides a practical and efficient approach to construct thioethers, using readily available aromatic amines and alkyl halides as starting materials. Sensitive and synthetic useful functional groups could be tolerated. Furthermore, pharmaceuticals, glucose, an amino acid, and a chiral ligand are successfully furnished by this late-stage sulfuration strategy.
• Reactions of Benzyl Aryl Sulfides with Excess Active Halogen Reagents
  作者：Mingde Xia、Shaowu Chen、Dallas K. Bates

  DOI：10.1021/jo961565+

  日期：1996.1.1

  1,2,3-Tribromopyrrolo[1,2-b][1,2]benzothiazin-10-one (2) is produced from 2-[2-(benzylthio)benzoyl]pyrrole (1) when treated with excess (5 equiv) NBS in CHCl3. With NCS, a mixture is obtained in which di- and trichloropyrrolo[1,2-b][1,2]benzothiazin-10-ones are present. If ethanol is present in the NCS reaction, compound 4 Is formed as the major product. Further, compound 3 is also formed by the reaction of compound 1 or the corresponding disulfide with excess SOCl2. A novel route to alkyl arenesulfinic esters is also reported: Treatment of a benzyl aryl sulfide with excess (5 equiv) NCS in the presence of an n-alkyl alcohol (7 equiv) produces an n-alkyl arenesulfinic ester in good yield. An arenesulfonyl chloride is the major product in the presence of benzyl alcohol.
• N-(2-Alkoxycarbonylbenzenesulfenyl)benzimidazoles as Nitrogen-, Sulfur-, and Carbon-Sulfenylation Reagents
  作者：Masao Shimizu、Hidenori Fukazawa、Junﾕichi Inoue、Yoshimoto Abe、Takeo Konakahara

  DOI：10.3987/com-06-10904

  日期：——

  N-(2-Alkoxycarbonylbenzenesulfenyl)benzimidazoles reacted with nucleophiles such as amides, imidates, thiols, Grignard reagents, and active methylene compounds to yield the corresponding sulfenylated products: N-acylsulfenamides, N-sulfenylimidates, disulfides, sulfides, and sulfenylated active methylene compounds, respectively.
• Reactions of N-sulfenyl-1,2-benzisothiazolin-3-ones with nucleophiles
  作者：Ming Bao、Masao Shimizu、Shigeru Shimada、Jun'ichi Inoue、Takeo Konakahara

  DOI：10.1016/j.tet.2004.09.093

  日期：2004.12

  Reactions of N-[2-(alkoxycarbonyl)benzenesulfenyl]-1,2-benzisothiazolin-3-ones (1) with various nucleophiles were examined. Anions of active methylene compounds attacked the sulfur atoms of the suffenyl moieties of I to afford sulfide compounds, while thiols attacked the sulfur atoms of the benzisothiazolinone moieties of 1 to afford ring-opened products. Grignard reagents attacked both the above sulfur atoms to give ring-opened products along with sulfide compounds. (C) 2004 Published by Elsevier Ltd.