S-octyl 4-methoxybenzothioate | 86763-31-7

• 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: S-octyl 4-methoxybenzothioate
• 英文别名: S-octyl p-methoxybenzoate；S-octyl 4-methoxybenzenecarbothioate
• CAS: 86763-31-7
• 化学式: C₁₆H₂₄O₂S
• 分子量: 280.431
• InChiKey: WXEYNKBHAVYZKR-UHFFFAOYSA-N

物化性质

• 沸点：
  384.9±34.0 °C(Predicted)
• 密度：
  1.021±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.7
• 重原子数：
  19
• 可旋转键数：
  10
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.56
• 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：

  S-(2-methoxy)ethyl benzothioate 、 S-octyl 4-methoxybenzothioate 在 [RhCl(PPh₃)] 作用下， 以 various solvent(s) 为溶剂， 反应 4.5h， 以48%的产率得到辛硫苯酯
  参考文献：
  名称：

  Rhodium-catalyzed alkylthio exchange reaction of thioester and disulfide

  摘要：

  The Wilkinson complex RhCl(PPh3)(3) catalyzes equilibrating alkylthio exchange reaction of thioesters with disulfides. The treatment of a thioester and a dialkyl disulfide in refluxing diethyl ketone in the presence of RhCl(PPh3)(3) (2.5 mol %) for 1.5 h gave an alkylthio exchanged thioester. The reaction of S-methyl ester was conducted shifting the equilibrium by removing volatile dimethyl disulfide. (c) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2008.01.109
• 作为产物：
  描述：

  4-甲氧基苯甲酸酐 在 硫脲 作用下， 以 水 为溶剂， 反应 2.0h， 生成 S-octyl 4-methoxybenzothioate
  参考文献：
  名称：

  使用苯甲酸酐和硫脲原位生成硫代苯甲酸，一锅法无味合成硫酯。

  摘要：

  一种高效、无味的方法，通过苯甲酸酐、硫脲和各种有机卤化物（伯卤化物、烯丙基卤化物和苄基卤化物）或结构多样的缺电子烯烃（酮、酯和腈）的反应来一锅合成硫酯。 Et3N 的存在已被开发出来。在该方法中，硫脲与苯甲酸酐反应原位生成硫代苯甲酸，苯甲酸酐与缺电子烯烃进行共轭加成或与卤代烷发生亲核置换反应。

  DOI：

  10.3762/bjoc.11.141

文献信息

• A Novel Synthesis of Thiocarboxylic<i>S</i>-Esters from 1-(Acylthio)ethaniminium Halides and Alkyl Halides Using Liquid-Liquid Phase-Transfer Catalysis
  作者：Toshio Takido、Masaharu Toriyama、Kunio Itabashi

  DOI：10.1055/s-1988-27595

  日期：——

  S-Alkyl, S-benzyl, and S-(2-alkenyl) thiocarboxylates are prepared in good yields by acylation of thioacetamide with aryl halides and reaction of the resultant 1-(acylthio)ethaniminium halides with alkyl halides under liquid-liquid phase-transfer conditions.

  S-烷基、S-苄基和S-(2-烯基)硫代羧酸盐可通过硫代乙酰胺与芳基卤化物的酰化反应，并在液-液相转移条件下，将生成的1-(酰硫基)乙亚胺基卤化物与烷基卤化物反应得到，产率良好。
• Microwave-Assisted Direct Thioesterification of Carboxylic Acids
  作者：Yen-Lin Chou、Yi Jhong、Sharada Prasanna Swain、Duen-Ren Hou

  DOI：10.1021/acs.joc.7b01705

  日期：2017.10.6

  N′-diphenylthiourea, triethylamine, and primary alkyl halides is described. Microwave-assisted heating and a catalytic amount of 4-(dimethylamino)pyridine (DMAP) further improved the yields. Both aromatic and aliphatic carboxylic acids were converted to the corresponding thioesters, and many functional groups were compatible with this reaction. Several possible reaction intermediates were investigated, and the

  描述了直接从羧酸，N，N'-二苯基硫脲，三乙胺和伯烷基卤化物一锅法合成硫酯的方法。微波辅助加热和催化量的4-（二甲基氨基）吡啶（DMAP）进一步提高了收率。芳族和脂族羧酸均被转化为相应的硫酯，并且许多官能团与该反应相容。研究了几种可能的反应中间体，衍生自烷基卤化物和叔胺的季铵盐是生产硫酯的中间体。提出了这种硫酯化反应的新反应机理。
• Pd-Catalyzed Thiocarbonylation with Stoichiometric Carbon Monoxide: Scope and Applications
  作者：Mia N. Burhardt、Rolf H. Taaning、Troels Skrydstrup

  DOI：10.1021/ol400138m

  日期：2013.2.15

  A general protocol for the Pd-catalyzed thiocarbonylation of aryl iodides with stoichiometric carbon monoxide has been established employing a catalytic system composed of Pd(OAc)(2) and DPEphos with low catalyst loading (1 mol %). Both electron-rich and -deficient aryl iodides proved effective for these couplings with aryl and alkyl thiols. The choice of the metal ligands and the solvent system was crucial for the efficiency and chemoselectivity of these transformations.
• One-pot odourless synthesis of thioesters via in situ generation of thiobenzoic acids using benzoic anhydrides and thiourea
  作者：Mohammad Abbasi、Reza Khalifeh

  DOI：10.3762/bjoc.11.141

  日期：——

  efficient and odourless procedure for a one-pot synthesis of thioesters by the reaction of benzoic anhydrides, thiourea and various organic halides (primary, allylic, and benzylic) or structurally diverse, electron-deficient alkenes (ketones, esters, and nitriles) in the presence of Et3N has been developed. In this method, thiobenzoic acids were in situ generated from the reaction of thiourea with benzoic anhydrides

  一种高效、无味的方法，通过苯甲酸酐、硫脲和各种有机卤化物（伯卤化物、烯丙基卤化物和苄基卤化物）或结构多样的缺电子烯烃（酮、酯和腈）的反应来一锅合成硫酯。 Et3N 的存在已被开发出来。在该方法中，硫脲与苯甲酸酐反应原位生成硫代苯甲酸，苯甲酸酐与缺电子烯烃进行共轭加成或与卤代烷发生亲核置换反应。
• Rhodium-catalyzed alkylthio exchange reaction of thioester and disulfide
  作者：Mieko Arisawa、Tomohiro Kubota、Masahiko Yamaguchi

  DOI：10.1016/j.tetlet.2008.01.109

  日期：2008.3

  The Wilkinson complex RhCl(PPh3)(3) catalyzes equilibrating alkylthio exchange reaction of thioesters with disulfides. The treatment of a thioester and a dialkyl disulfide in refluxing diethyl ketone in the presence of RhCl(PPh3)(3) (2.5 mol %) for 1.5 h gave an alkylthio exchanged thioester. The reaction of S-methyl ester was conducted shifting the equilibrium by removing volatile dimethyl disulfide. (c) 2008 Elsevier Ltd. All rights reserved.