4-(benzo[d]oxazol-2'-ylthio)benzene-1,2-diol

• 分子结构分类: 有机化合物 - 有机硫化合物 - 硫醚类
• 英文名称: 4-(benzo[d]oxazol-2'-ylthio)benzene-1,2-diol
• 英文别名: 4-(1,3-Benzoxazol-2-ylsulfanyl)benzene-1,2-diol
• 化学式: C₁₃H₉NO₃S
• 分子量: 259.285
• InChiKey: FIRKQCYIQAAMCQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  18
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  91.8
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  2-氨基苯酚 在 dipotassium peroxodisulfate 、 三氟甲磺酸 作用下， 以 乙醇 、 水 、 乙腈 为溶剂， 反应 10.0h， 生成 4-(benzo[d]oxazol-2'-ylthio)benzene-1,2-diol
  参考文献：
  名称：

  Regioselective Thiolation of Arenes and Heteroarenes: C–H Functionalization Strategy for C–S Bond Formation

  摘要：

  A facile transition-metal-free oxidative cross-dehydrogenative coupling reaction involving selective formation of a C-S bond leading to the synthesis of arylthiobenzoxazoles, heteroarylthiobenzoxazoles, and arylthiobenzothiazoles has been described. This highly regioselective C-H functionalization reaction with electron-rich aromatic systems including heteroaromatics is achieved by reversing the reactivity of sulfur in the presence of a suitable oxidant and strong acid.

  DOI：

  10.1021/jo501793q

文献信息

• 一种合成儿茶酚硫醚类化合物的方法
  申请人：郑州大学

  公开号：CN113185476B

  公开（公告）日：2023-09-12

  本发明提供了一种合成儿茶酚硫醚类化合物的方法，以没食子酸为催化剂，金属盐为助催化剂，在氧气或空气环境中，使儿茶酚类化合物与硫醇类化合物在水和有机溶剂作混合溶剂中、碱存在条件下反应生成儿茶酚硫醚类化合物。本发明催化剂廉价，简单，催化活性高，反应效率高；合成工艺简捷，废物少，环境友好，具有较强的工业应用前景。
• Laccase-catalyzed synthesis of catechol thioethers by reaction of catechols with thiols using air as an oxidant
  作者：Heba T. Abdel-Mohsen、Jürgen Conrad、Uwe Beifuss

  DOI：10.1039/c3gc41968a

  日期：——

  The laccase-catalyzed reaction between catechols and thiols using aerial oxygen as the oxidant delivers the corresponding catechol thioethers with yields up to 96% under mild reaction conditions.

  使用空气中的氧气作为氧化剂，儿茶酚和硫醇之间的漆酶催化反应可在温和的反应条件下提供相应的邻苯二酚硫醚，产率高达96％。
• Electroorganic Synthesis of Catecholthioethers
  作者：Davood Nematollahi、Esmail Tammari

  DOI：10.1021/jo0508301

  日期：2005.9.1

  It is demonstrated that o-quinones, generated by the electrochemically driven oxidation of the catechols (1a−d) at physiological pH, are rapidly scavenged by 2-mercaptobenzoxazole (3) to give related catecholthioethers (4a−d) via an EC electrochemical mechanism pathway. The electrochemical syntheses of 4a−d have been successfully performed in one-pot in ambient conditions and in an undivided cell using

  据证实Ó -quinones，由儿茶酚（的电化学从动氧化产生1A - d）在生理pH下，正在迅速由2-巯基苯并恶唑（扫气3），得到相关catecholthioethers（4A - d）经由EC电化学机构途径。使用具有高原子经济性的环境友好方法，已在环境条件下在一锅中和一个未分隔的电池中成功地完成了4a - d的电化学合成。
• Synthesis of catecholthioethers by the selective oxidation of catechols in competition with 2-mercaptobenzoxazole
  作者：Esmail Tammari、Naser Mirazi、Davood Nematollahi

  DOI：10.1070/mc2006v016n05abeh002343

  日期：2006.1

  Potassium ferricyanide acts as a selective oxidising agent for the oxidation of catechols even in the presence of 2-mercaptobenzoxazole, as an easily oxidisable thiol to produce related catechol thioethers.
• Regioselective Thiolation of Arenes and Heteroarenes: C–H Functionalization Strategy for C–S Bond Formation
  作者：Begur Vasanthkumar Varun、Kandikere Ramaiah Prabhu

  DOI：10.1021/jo501793q

  日期：2014.10.17

  A facile transition-metal-free oxidative cross-dehydrogenative coupling reaction involving selective formation of a C-S bond leading to the synthesis of arylthiobenzoxazoles, heteroarylthiobenzoxazoles, and arylthiobenzothiazoles has been described. This highly regioselective C-H functionalization reaction with electron-rich aromatic systems including heteroaromatics is achieved by reversing the reactivity of sulfur in the presence of a suitable oxidant and strong acid.