2-Phenylthiohexansaeureethylester | 156730-69-7

• 分子结构分类: 有机化合物 - 有机硫化合物 - 硫醚类
• 英文名称: 2-Phenylthiohexansaeureethylester
• 英文别名: Ethyl 2-phenylsulfanylhexanoate
• CAS: 156730-69-7
• 化学式: C₁₄H₂₀O₂S
• 分子量: 252.378
• InChiKey: YVDYGNOASYYQKC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.5
• 重原子数：
  17
• 可旋转键数：
  8
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.5
• 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：

  2-Phenylthiohexansaeureethylester 在 lithium aluminium tetrahydride 作用下， 以 乙醚 为溶剂， 反应 6.0h， 生成 2-Phenylsulfanyl-hexan-1-ol
  参考文献：
  名称：

  Do the Electronic Effects of Sulfur Indeed Control the π-Selectivity of γ-Sulfenyl Enones? An Investigation

  摘要：

  The electronic effects of sulfur in gamma-sulfenyl enones are not transmitted to the carbonyl carbon through the pi bond as reported previously. The diastereoselectivity is rather controlled by a combination of several other factors. The steric effects arising from the substituents on the sulfur atom and the gamma-carbon and the bulk of the nucleophile constitute the major control elements.

  DOI：

  10.1021/jo034608c
• 作为产物：
  描述：

  正丁基丙二酸二乙酯 以40%的产率得到
  参考文献：
  名称：

  ASAOKA M.; MIYAKE K.; TAKEI H., BULL. CHEM. SOC. JAP., 1978, 51, NO 10, 3008-3010

  摘要：

  DOI：

文献信息

• Stannyl Radical-Mediated Cleavage of π-Deficient Heterocyclic Sulfones. Synthesis of α-Fluoro Esters
  作者：Stanislaw F. Wnuk、Jeannette M. Rios、Jahanzeb Khan、Ya-Li Hsu

  DOI：10.1021/jo000342n

  日期：2000.6.1

  1 h under these conditions. This represents a mild new methodology for removal of the synthetically useful sulfone moiety. Substitution of Bu(3)SnD for Bu(3)SnH gave access to alpha-deuterium-labeled esters. Treatment of the alpha-(pyrimidin-2-ylsulfonyl) enolates derived from several esters with Selectfluor gave high yields of the 2-fluoro-2-(pyrimidin-2-ylsulfonyl)alkanoates, which were smoothly

  用三丁基锡烷和偶氮双（2-甲基-2-丙腈）（AIBN）在苯中回流处理2-（吡啶-2-基磺酰基）己酸乙酯36小时，导致氢解生成己酸乙酯（60％），而没有回流48小时后，观察到与2-（苯磺酰基）己酸乙酯反应。在这些条件下，在1小时内对2-（嘧啶-2-基磺酰基）己酸乙酯进行定量氢解。这代表了去除合成上有用的砜部分的温和的新方法。用Bu（3）SnD代替Bu（3）SnH可以访问α-氘标记的酯。用Selectfluor处理衍生自几种酯的α-（嘧啶-2-基磺酰基）烯醇酸酯，可高产率地生产2-氟-2-（嘧啶-2-基磺酰基）链烷酸酯，将其平滑地进行磺酰化[Bu（3）SnH（2当量）/ AIBN /苯/δ]，得到2-氟链烷酸酯。在氟化钾的存在下，由氯化三苯甲基氯化锡（0.15当量）和过量的聚甲基氢硅氧烷生成的“催化”氢化锡，还以高收率实现了从酸衍生物中去除pi不足的α-（嘧啶-2-基磺酰基）部分。建议通过烷氧基酮基型自由基和烯醇锡进行脱磺酰化。
• Sulfenylation Accompanied by Dealkoxycarbonylation of β-Keto Esters, Geminal Diesters, and α-Cyano Ester in Hexamethylphosphoric Triamide (HMPA)
  作者：Morio Asaoka、Kazutoshi Miyake、Hisashi Takei

  DOI：10.1246/bcsj.51.3008

  日期：1978.10

  In the presence of sodium iodide, diphenyl disulfide reacted with geminal diesters, β-keto esters, and α-cyano esters in hexamethylphosphoric triamide (HMPA) at 150–160 °C to give alkyl phenyl sulfides and α-phenylthio esters, ketones, and nitriles, respectively, along with evolution of carbon dioxide.

  在碘化钠存在下，二苯基二硫化物在 150-160 °C 的温度下与六甲基三磷酰胺 (HMPA) 中的宝石二酯、β-酮酯和α-氰酯发生反应，分别生成烷基苯基硫化物和α-苯基硫代酯、酮和腈，同时产生二氧化碳。
• Solid-Liquid Phase Transfer Catalytic Synthesis. XI. The Convenient and Efficient Alkylation of Ethyl Phenylmercapto-Acetate in the Presence of Quaternary Ammonium Salts Under Microwave Irradiation
  作者：Runhua Deng、Yuliang Wang、Yaozhong Jiang

  DOI：10.1080/00397919408010199

  日期：1994.7

  Abstract The rapid alkylation of ethyl phenylmercapto—acetate with a series of halides was performed in 650W domestic microwave oven to yield the alkylated products in 58 to 83%.

  摘要 苯巯基乙酸乙酯与一系列卤化物在650W家用微波炉中进行快速烷基化反应，烷基化产物的产率为58%～83%。
• Stannyl Radical-Mediated Cleavage of π-Deficient Heterocyclic Sulfones. Synthesis of α-Fluoro Esters and the First Homonucleoside α-Fluoromethylene Phosphonate¹
  作者：Stanislaw F. Wnuk、Morris J. Robins

  DOI：10.1021/ja953513s

  日期：1996.1.1
• Do the Electronic Effects of Sulfur Indeed Control the π-Selectivity of γ-Sulfenyl Enones? An Investigation
  作者：Veejendra K. Yadav、K. Ganesh Babu、Masood Parvez

  DOI：10.1021/jo034608c

  日期：2004.5.1

  The electronic effects of sulfur in gamma-sulfenyl enones are not transmitted to the carbonyl carbon through the pi bond as reported previously. The diastereoselectivity is rather controlled by a combination of several other factors. The steric effects arising from the substituents on the sulfur atom and the gamma-carbon and the bulk of the nucleophile constitute the major control elements.