S-乙基噻吩-3-硫代甲酸酯 | 333355-28-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 噻吩类
• 中文名称: S-乙基噻吩-3-硫代甲酸酯
• 英文名称: 3-Thiophenecarbothioic acid, S-ethyl ester
• 英文别名: S-ethyl thiophene-3-carbothioate
• CAS: 333355-28-5
• 化学式: C₇H₈OS₂
• 分子量: 172.272
• InChiKey: GUAHQVACISEYRA-UHFFFAOYSA-N

物化性质

• 沸点：
  242.5±22.0 °C(Predicted)
• 密度：
  1.222±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  10
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  70.6
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  ethyl pentanoate,iodozinc(1+) 、 S-乙基噻吩-3-硫代甲酸酯 在 5% Pd(OH)₂/C 、 N,N-二甲基甲酰胺 作用下， 以 四氢呋喃 、 甲苯 为溶剂， 反应 68.0h， 生成 乙基6-氧代-6-(3-噻吩基)己酸酯
  参考文献：
  名称：

  SYNTHESIS OF MULTI-FUNCTIONALIZED KETONES THROUGH THE FUKUYAMA COUPLING REACTION CATALYZED BY PEARLMAN'S CATALYST: PREPARATION OF ETHYL 6-OXOTRIDECANOATE

  摘要：

  DOI：

  10.15227/orgsyn.084.0285

文献信息

• A Practical Synthesis of Multifunctional Ketones through the Fukuyama Coupling Reaction
  作者：Yoshikazu Mori、Masahiko Seki

  DOI：10.1002/adsc.200600610

  日期：2007.8.6

  A highly efficient, robust and scalable protocol for the synthesis of multifunctional ketones through Fukuyama coupling, i.e., cross-coupling of thiol esters with zinc reagents, has been developed. Treatment of thiol esters with alkylzinc iodides or dialkyl zincs in the presence of palladium on activated carbon (Pd/C) or palladium acetate [Pd(OAc)2] furnished the corresponding ketones in high yields

  已经开发出一种通过福山偶联法合成硫酮的高效，稳健和可扩展的方案，即硫醇酯与锌试剂的交叉偶联。在活性炭上钯（Pd / C）或乙酸钯[Pd（OAc）2 ]存在下，用烷基碘化锌或二烷基锌处理硫醇酯可提供相应的酮，收率很高。对Pd / C催化反应的性质-活性关系的评估已证明，在硫代内酯1a与锌试剂2a反应中，氧化Pd / C比还原的Pd / C更有效。。基于Pd / C催化反应对Pd / C性质的依赖性以及Pd从Pd / C浸出到溶液中的程度，Pd / C催化福山偶联反应的双重反应机理提出了包括多相和均相催化循环的方法。当添加溴化锌时，锌试剂的显着减少和Pd（OAc）2的使用量大大减少。这支持一个假设，其中从无效二烷基锌（R施兰克平衡的移位2 Zn）的活性有机锌物种，例如烷基锌卤化物（RZnX）和三个坐标物种[（RZnX 2）- ⋅（ZNX）+在反应期间生成稳定的单体Pd络合物可以促进反应。
• A novel procedure for the synthesis of multifunctional ketones through the Fukuyama coupling reaction employing dialkylzincs
  作者：Yoshikazu Mori、Masahiko Seki

  DOI：10.1016/j.tetlet.2004.07.148

  日期：2004.9

  Treatment of thiol esters 1 with dialkylzincs 2 in the presence of zinc bromide, that was in situ prepared from zinc dust and bromine, provided various functionalized ketones 3 in high yields. The reaction mechanism, which may shift the Schlenk equilibrium from dialkylzincs 2 to reactive alkylzinc bromide 5, was postulated to account for the facile coupling reaction. (C) 2004 Elsevier Ltd. All rights reserved.
• Pd(OH)₂/C (Pearlman's Catalyst):  A Highly Active Catalyst for Fukuyama, Sonogashira, and Suzuki Coupling Reactions
  作者：Yoshikazu Mori、Masahiko Seki

  DOI：10.1021/jo0265277

  日期：2003.2.1

  Treatment of thiol esters 1 with zinc reagent 2 in the presence of a small amount (
• Palladium on charcoal-catalyzed Fukuyama coupling reaction
  作者：Toshiaki Shimizu、Masahiko Seki

  DOI：10.1016/s0040-4039(00)01984-5

  日期：2001.1

  The Pd/C-catalyzed coupling reactions of thiol esters 1 with a zinc reagent 2 were accomplished in the presence of DMF leading to the polyfunctional ketones 3 in good yields under mild reaction conditions. The protocol was applied to the coupling reaction of a thiolactone 4c with a zinc reagent 2 to provide, after dehydration, a dehydrobiotin derivative 5c in 94% yield. (C) 2001 Elsevier Science Ltd. All rights reserved.
• SYNTHESIS OF MULTI-FUNCTIONALIZED KETONES THROUGH THE FUKUYAMA COUPLING REACTION CATALYZED BY PEARLMAN'S CATALYST: PREPARATION OF ETHYL 6-OXOTRIDECANOATE
  作者：Mori, Yoshikazu、Seki, Masahiko、Aoyama, Naohiro、Shibasaki, Masakatsu

  DOI：10.15227/orgsyn.084.0285

  日期：——