S-(2,6-dimethylphenyl) ethanethioate | 94764-21-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯硫酚酯
• 英文名称: S-(2,6-dimethylphenyl) ethanethioate
• 英文别名: (2,6-Dimethyl-phenyl)-thiolacetat；Thioessigsaeure-<2,6-dimethyl-phenyl>-ester；2,6-Dimethylbenzenethiol, S-acetyl-
• CAS: 94764-21-3
• 化学式: C₁₀H₁₂OS
• 分子量: 180.271
• InChiKey: UWFDUOBIXFDFCT-UHFFFAOYSA-N

物化性质

• 沸点：
  129 °C(Press: 11 Torr)
• 密度：
  1.08±0.1 g/cm3(Predicted)
• 保留指数：
  1420.7

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  12
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  42.4
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  S-(2,6-dimethylphenyl) ethanethioate 在 磺酰氯 、 乙酸酐 作用下， 反应 20.0h， 以97%的产率得到2,6-dimethylbenzenesulfinyl chloride
  参考文献：
  名称：

  Cevasco, Giorgio; Novi, Marino; Petrillo, Giovanni, Gazzetta Chimica Italiana, 1990, vol. 120, # 2, p. 131 - 133

  摘要：

  DOI：
• 作为产物：
  描述：

  钠硫代乙酸盐 、 2,6-dimethylbenzenediazonium o-benzenedisulfonimide 以 乙腈 为溶剂， 反应 0.08h， 以87%的产率得到S-(2,6-dimethylphenyl) ethanethioate
  参考文献：
  名称：

  Barbero, Margherita; Degani, Iacopo; Dughera, Stefano, Synthesis, 2003, # 8, p. 1225 - 1230

  摘要：

  DOI：

文献信息

• [EN] ISATOIC ANHYDRIDE DERIVATIVES AND APPLICATIONS THEREOF<br/>[FR] DÉRIVÉS D'ANHYDRIDE ISATOÏQUE ET LEURS APPLICATIONS
  申请人：UNIV NORTH CAROLINA

  公开号：WO2015163952A1

  公开（公告）日：2015-10-29

  Isatoic anhydride derivatives having an N-substituent which includes a quaternary ammonium group are useful for labeling and/or functionalizing a target material and/or for coupling materials together. The isatoic anhydride derivatives of the present disclosure can be advantageously water soluble, easily prepared and purified. Isatoic anhydride derivatives useful in the present disclosure preferably have at least one chemically reactive group or at least one binding group or at least one detectable label. Anthranilate derivatives made from the isatoic anhydrides derivatives or otherwise and kits including the isatoic anhydride derivatives are also disclosed.

  异烟酰亚胺衍生物具有包括季铵基团的N-取代基，可用于标记和/或功能化目标材料和/或将材料耦合在一起。本公开的异烟酰亚胺衍生物可以具有优势的水溶性，易于制备和纯化。本公开中有用的异烟酰亚胺衍生物最好至少具有一个化学反应性基团或至少一个结合基团或至少一个可检测标记。从异烟酰亚胺衍生物制备的邻氨基苯甲酸酯衍生物或其他衍生物以及包括异烟酰亚胺衍生物的试剂盒也被公开。
• Isatoic anhydride derivatives and applications thereof
  申请人：The University of North Carolina at Charlotte

  公开号：US10179175B2

  公开（公告）日：2019-01-15

  Isatoic anhydride derivatives having an N-substituent which includes a quaternary ammonium group are useful for labeling and/or functionalizing a target material and/or for coupling materials together. The isatoic anhydride derivatives of the present disclosure can be advantageously water soluble, easily prepared and purified. Isatoic anhydride derivatives useful in the present disclosure preferably have at least one chemically reactive group or at least one binding group or at least one detectable label. Anthranilate derivatives made from the isatoic anhydrides derivatives or otherwise and kits including the isatoic anhydride derivatives are also disclosed.

  具有包括季铵基团的 N 取代基的异酸酐衍生物可用于标记和/或官能化目标材料和/或将材料耦合在一起。本公开的异酸酐衍生物可溶于水，易于制备和纯化。本公开中有用的异酸酐衍生物最好具有至少一个化学反应基团或至少一个结合基团或至少一个可检测标签。此外，还公开了由异酸酐衍生物或其他衍生物制成的蒽酸衍生物以及包括异酸酐衍生物的试剂盒。
• Electronic Effects in a Green Protocol for (Hetero)Aryl-S Coupling
  作者：Massimo Carraro、Camillo Are、Ugo Azzena、Lidia De Luca、Silvia Gaspa、Giuseppe Satta、Wolfgang Holzer、Vittorio Pace、Luisa Pisano

  DOI：10.3390/molecules29081714

  日期：——

  Aryl and heteroaryl iodides have been efficiently converted into the corresponding thioacetates in cyclopentyl methyl ether (CPME), a green solvent, under Cu catalysis. The chemoselectivity of the reaction is mainly controlled by electronic factors, enabling the conversion of both electron-rich and electron-deficient substrates into the corresponding thioacetates in good to excellent yields. The products

  在铜催化下，芳基和杂芳基碘化物在绿色溶剂环戊基甲基醚（CPME）中有效转化为相应的硫代乙酸酯。该反应的化学选择性主要受电子因素控制，使富电子和缺电子底物都能以良好至优异的产率转化为相应的硫代乙酸盐。产物可以很容易地脱保护为相应的硫醇盐，以进行额外的原位合成转化。令人惊讶的是，尽管 CPME 的介电常数相对较低，但在微波辐射条件下进行时，反应速率显着提高。该合成方法在绿色溶剂 CPME 中使用安全且廉价的 CuI 预催化剂，表现出对官能团的显着耐受性、温和的反应条件和广泛的底物范围。非水后处理允许完全回收催化剂和溶剂，使该方法成为 C(sp2) 硫官能化的环境可持续方案。此外，该反应显示出与碘化物与氯化物和溴化物竞争的选择性交叉偶联，使其可用于多步合成。为了证明该方法的潜力，将其应用于光致变色二噻吩乙烯的高产率合成，此前尚未报道过选择性合成。
• Nickel-Mediated Formation of Thio Esters from Bound Methyl, Thiols, and Carbon Monoxide: A Possible Reaction Pathway of Acetyl-Coenzyme A Synthase Activity in Nickel-Containing Carbon Monoxide Dehydrogenases
  作者：Gregory C. Tucci、R. H. Holm

  DOI：10.1021/ja00129a011

  日期：1995.6

  Current mechanistic proposals for the acetyl synthase activity of nickel-containing carbon monoxide dehydrogenases (CH3-THF + CoA . SH --> CoA . SCOCH3 + THF; THF = tetrahydrofolate, CoA . SH = coenzyme A) implicate a Ni catalytic center and the steps [Ni-CH3] --> [Ni-COCH3] --> CoA . SCOCH3. The second step presumably involves attack by the sulfur nucleophile of coenzyme A at the acyl carbon atom in the overall reaction [Ni-II-COCH3] + RS(H) --> RSCOCH(3) + Ni-II (+ H+) + 2e(-). We have previously demonstrated these steps in Ni(II) complexes with physiological-type ligation. In this work, it is shown that the reaction of acyl and thiolate ligands coordinated to Ni(II) affords thioesters in high yield, The complex [Ni(bpy)(CH3)(2)], established to be planar by an X-ray structure determination, reacts with 1 equiv of arenethiol to afford diamagnetic planar [Ni(bpy)(CH3)(SR)] (8) with R = p-C6H4CH3, 2,6-C6H3(CH3)2 (8b), mesityl (8c), 2,4,6-C(6)H(2)iPr(3), and 2,6-C6H3Cl2 (8e) (bpy = 2,2'-bipyridyl). An analogous reaction gives [Ni(bpy)(C2H5)(S-mesityl)] (12) from [Ni(bpy)(C2H5)(2)]. Planar structures of 8c,e were confirmed by X-ray analysis. Complexes 12 and 8 with different R substituents undergo thiolate ligand exchange in THF with K-eq approximate to 1. Reaction of 8e with 1 equiv of carbon monoxide yields the acyl complex [Ni(bpy)(COCH3)(S-2,6-C6H3Cl2)] (9a), whose planar coordination unit was confirmed by X-ray methods. Treatment of the complexes 8 in THF with more than 3 equiv of carbon monoxide yields [Ni(bpy)(CO)(2)] and the thioesters RSCOCH(3) in 96-100% yield in situ. A solution initially containing 8b and 12 gave under the same conditions four thioesters in equal amounts, consistent with four complexes in the equilibrated solution prior to reaction with carbon monoxide. Reaction of 9a in THF with carbon monoxide produced 2,6-dichlorophenyl thioacetate quantitatively, indicating that Ni(II)-acyl-thiolate complexes are intermediates in thioester formation. The overall reaction is [Ni(bpy)(R')(SR)] + 3CO --> RSCOR' + [Ni(bpy)(CO)2] (R' = CH3, C2H5); the two electrons in the generalized reaction are captured by the metal as Ni(0). A related and necessarily intramolecular reaction of [Ni(bpy)(SCH2CH2CH2)] was confirmed and shown to produce gamma-thiobutyrolactone in quantitative yield in situ. Evidence supporting an analogous intramolecular path for reaction systems based on 8 is summarized. This investigation provides the first examples of Ni-mediated acyclic thioester synthesis and demonstrates a possible means of enzymatic thioester formation should coenzyme A(-) and an acetyl group coordinate to the Ni(II) catalytic center.
• CEVASCO, GIORGIO;NOVI, MARINO;PETRILLO, GIOVANNI;THEA, SERGIO, GAZZ. CHIM. ITAL., 120,(1990) N, C. 131-133
  作者：CEVASCO, GIORGIO、NOVI, MARINO、PETRILLO, GIOVANNI、THEA, SERGIO

  DOI：——

  日期：——