2-[(2-氧丙基)硫代]苯甲酸甲酯 | 53278-21-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 中文名称: 2-[(2-氧丙基)硫代]苯甲酸甲酯
• 英文名称: methyl 2-<(2-oxopropyl)thio>benzoate
• 英文别名: 1-(o-tolylthio)propan-2-one；α-<2'-Carbmethoxy-phenylmercapto)-aceton；α-[2'-Carbmethoxy-phenylmercapto)-aceton；Methyl 2-[(2-oxopropyl)thio]benzoate；methyl 2-(2-oxopropylsulfanyl)benzoate
• CAS: 53278-21-0
• 化学式: C₁₁H₁₂O₃S
• mdl: MFCD00209313
• 分子量: 224.28
• InChiKey: LXFGVTCWUZZPHD-UHFFFAOYSA-N

物化性质

• 熔点：
  60 °C

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  15
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.272
• 拓扑面积：
  68.7
• 氢给体数：
  0
• 氢受体数：
  4

安全信息

• 海关编码：
  2930909090

反应信息

• 作为反应物：
  描述：

  2-[(2-氧丙基)硫代]苯甲酸甲酯 在 PPA 、 Polyphosphoric acid (PPA) 、 溴 、 二异丁基氢化铝 、 potassium carbonate 、 1,2-双(二苯基膦)乙烷 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 、 甲苯 为溶剂， 反应 1.5h， 生成 ((Z)-6,6-Dimethyl-hept-2-en-4-ynyl)-methyl-(3-methyl-benzo[b]thiophen-7-ylmethyl)-amine
  参考文献：
  名称：

  Synthesis and structure-activity relationships of benzo[b]thienylallylamine antimycotics

  摘要：

  Benzo[b]thiophene analouges of the allylamine antimycotic terbinafine (2) bearing the side chain at various positions and optionally substituted by halogen have been prepared and their antifungal activity studied. Derivatives bearing the side chain at positions 3, 4, or 7 are bioequivalents of 2. Compounds containing the allylamine side chain at position 7, with a further substituent at position 3, showed significantly enhanced activity against Candida albicans, an effect which appears to be specifically linked only to this particular substitution pattern. 3-Chloro-7-benzo[b]thienyl derivative 7m was found to be the most potent allylamine antimycotic identified so far. In general, substituted benzo[b]thiophenes can be used not only as potential equivalents of naphthalene in bioactive compounds but also as a tool to selectively modify biological activities.

  DOI：

  10.1021/jm00105a011
• 作为产物：
  描述：

  2,2,6,6-四甲基哌啶氧化物 、 硫代水杨酸甲酯 在 potassium carbonate 作用下， 以 N,N-二甲基乙酰胺 为溶剂， 反应 12.0h， 以38%的产率得到2-[(2-氧丙基)硫代]苯甲酸甲酯
  参考文献：
  名称：

  使用TEMPO作为C 3合成子，通过顺序氧化，骨架重排和CS键形成的反应级联反应合成α-芳硫基丙酮

  摘要：

  在这里，我们提出了从商业化的硫醇和普遍使用的TEMPO及其类似物到α-亚磺酰基化羰基化合物的空前途径，它们在简单且无金属的条件下通过骨架重排充当C 3合成子。机理研究表明，该反应涉及连续的自由基氧化和阳离子偶联过程。TEMPO类似物和硫醇分别在自由基过程中充当氧化剂和还原剂，而在偶联过程中，前者提供C 3合成子与相关的硫源偶联。

  DOI：

  10.1039/c9ob00018f

文献信息

• α-Benzoyloxylation of β-keto sulfides at ambient temperature
  作者：Enrico Piras、Francesco Secci、Pierluigi Caboni、Maria Francesca Casula、Angelo Frongia

  DOI：10.1039/c7ra10888e

  日期：——

  A facile and efficient protocol for the α-benzoyloxylation of β-keto sulfides is presented. This methodology provides a step-economical, mild and practical access to highly functionalized α-O-benzoyloxy substituted β-keto sulfides, including those with quaternary carbons, which are not easily obtained through currently available methods.

  提出了一种简便而有效的方案，用于β-酮硫醚的α-苯甲酰氧基化。这种方法学提供了经济高效，温和实用的步骤，可轻松获得高度官能化的α - O-苯甲酰氧基取代的β-酮硫醚，包括那些具有季碳的硫醚，而这些硫醚很难通过现有方法获得。
• Direct Synthesis of α-Sulfenylated Ketones under Electrochemical Conditions
  作者：Aline A. N. de Souza、Aloisio de A. Bartolomeu、Timothy J. Brocksom、Timothy Noël、Kleber T. de Oliveira

  DOI：10.1021/acs.joc.2c00147

  日期：2022.5.6
• NUSSBAUMER, PETER;PETRANYI, GABOR;STUTZ, ANTON, J. MED. CHEM., 34,(1991) N, C. 65-73
  作者：NUSSBAUMER, PETER、PETRANYI, GABOR、STUTZ, ANTON

  DOI：——

  日期：——
• Synthesis and structure-activity relationships of benzo[b]thienylallylamine antimycotics
  作者：Peter Nussbaumer、Gabor Petranyi、Anton Stuetz

  DOI：10.1021/jm00105a011

  日期：1991.1

  Benzo[b]thiophene analouges of the allylamine antimycotic terbinafine (2) bearing the side chain at various positions and optionally substituted by halogen have been prepared and their antifungal activity studied. Derivatives bearing the side chain at positions 3, 4, or 7 are bioequivalents of 2. Compounds containing the allylamine side chain at position 7, with a further substituent at position 3, showed significantly enhanced activity against Candida albicans, an effect which appears to be specifically linked only to this particular substitution pattern. 3-Chloro-7-benzo[b]thienyl derivative 7m was found to be the most potent allylamine antimycotic identified so far. In general, substituted benzo[b]thiophenes can be used not only as potential equivalents of naphthalene in bioactive compounds but also as a tool to selectively modify biological activities.
• Synthesis of α-arylthioacetones using TEMPO as the<i>C</i>₃synthon<i>via</i>a reaction cascade of sequential oxidation, skeletal rearrangement and C–S bond formation
  作者：Jiao-Xia Zou、Yi Jiang、Shuai Lei、Gao-Feng Yin、Xiao-Ling Hu、Quan-Yi Zhao、Zhen Wang

  DOI：10.1039/c9ob00018f

  日期：——

  pathway to α-sulfenylated carbonyl compounds from commercially available thiols and universally employed TEMPO and its analogues, which act as C3 synthons through skeletal rearrangement under simple and metal-free conditions. Mechanism studies suggest that this reaction involves a consecutive radical oxidation and cation coupling process. TEMPO analogues and thiols serve as oxidants and reductive reagents

  在这里，我们提出了从商业化的硫醇和普遍使用的TEMPO及其类似物到α-亚磺酰基化羰基化合物的空前途径，它们在简单且无金属的条件下通过骨架重排充当C 3合成子。机理研究表明，该反应涉及连续的自由基氧化和阳离子偶联过程。TEMPO类似物和硫醇分别在自由基过程中充当氧化剂和还原剂，而在偶联过程中，前者提供C 3合成子与相关的硫源偶联。