o-tolyl-dithiocarbamic acid ; compound with triethylamine | 53662-44-5

• 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: o-tolyl-dithiocarbamic acid ; compound with triethylamine
• 英文别名: o-Tolyl-dithiocarbamidsaeure; Verbindung mit Triaethylamin；N-(2-methylphenyl)carbamodithioate;triethylazanium
• CAS: 53662-44-5
• 化学式: C₆H₁₅N*C₈H₉NS₂
• 分子量: 284.49
• InChiKey: OLLIUWWFKSQORT-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.17
• 重原子数：
  18
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  49.6
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  o-tolyl-dithiocarbamic acid ; compound with triethylamine 在 吡啶 、 三光气 、 potassium hydroxide 作用下， 以 1,4-二氧六环 、 氯仿 、 水 为溶剂， 反应 10.5h， 生成 N-(3-(2-((4-(o-tolylamino)quinazolin-2-yl)thio)acetamido)phenyl)acrylamide
  参考文献：
  名称：

  Design, synthesis and biological evaluation of novel 2,4-disubstituted quinazoline derivatives targeting H1975 cells via EGFR-PI3K signaling pathway

  摘要：

  DOI：

  10.1016/j.bmc.2021.116265
• 作为产物：
  描述：

  二硫化碳 、 三乙胺 、 邻甲苯胺 以 四氢呋喃 为溶剂， 反应 20.0h， 生成 o-tolyl-dithiocarbamic acid ; compound with triethylamine
  参考文献：
  名称：

  甲苯磺酰氯的异硫氰酸盐介导原位生成的二硫代氨基甲酸盐的分解

  摘要：

  据报道，由烷基胺和芳基胺制备异硫氰酸酯的简便通用方法。该方法依赖于甲苯磺酰氯介导的二硫代氨基甲酸盐的分解，该二硫代氨基甲酸盐是通过用二硫化碳和三乙胺处理胺而原位产生的。利用该方案，我们以中等至极好的收率制备了19-烷基异硫氰酸酯和芳基异硫氰酸酯。

  DOI：

  10.1021/jo070246n

文献信息

• Cerium ammonium nitrate-catalyzed aerobic oxidative coupling of dithiocarbamates: facile synthesis of thioureas and bis(aminothiocarbonyl)disulfides
  作者：Tian-Tian Li、Xiang-Hai Song、Mei-Shuang Wang、Ning Ma

  DOI：10.1039/c4ra04628e

  日期：——

  Diverse disubstituted and trisubstituted thioureas were synthesized by the condensation of dithiocarbamate TEA (or DABCO) salts and amines using cerium ammonium nitrate (CAN) as a catalyst in high yields at room temperature. It is a one-pot method and it is unnecessary to isolate isothiocyanates. This reaction probably took place through nucleophilic addition of amines to isothiocyanates, which were generated by oxidative coupling of dithiocarbamates and the following decomposition of bis(aminothiocarbonyl)disulfides. When secondary amines and CS2 served as the reactants, bis(aminothiocarbonyl)disulfides were obtained via tandem nucleophilic addition/oxidative coupling reactions in moderate to excellent yields. In all the coupling reactions, the oxidant was air and CAN possibly acted as an SET catalyst.

  多种二取代和三取代硫脲通过二硫代氨基甲酸TEA（或DABCO）盐与胺在室温下使用硝酸铈铵（CAN）作为催化剂进行缩合反应，以高产率合成。这是一种一步法，无需分离异硫氰酸酯。该反应可能涉及胺对异硫氰酸酯的亲核加成，异硫氰酸酯是由二硫代氨基甲酸盐的氧化偶联以及随后双(氨基硫羰基)二硫化物的分解产生的。当使用二级胺和CS2作为反应物时，通过串联的亲核加成/氧化偶联反应，以中等至优异的产率获得了双(氨基硫羰基)二硫化物。在所有偶联反应中，氧化剂为空气，CAN可能作为单电子转移催化剂发挥作用。
• Copper promoted desulfurization towards the synthesis of isothiocyanates
  作者：UshaRani Mandapati、Srinivasarao Pinapati、RameshRaju Rudraraju

  DOI：10.1016/j.tetlet.2016.11.086

  日期：2017.1

  The cheap, readily available and air stable catalyst was used as the desulfurization agent for the conversion of aniline to isothiocyanates in one pot two step reaction under mild reaction conditions.

  在温和的反应条件下，通过一锅两步反应，将廉价，易于获得且空气稳定的催化剂用作脱硫剂，以将苯胺转化为异硫氰酸酯。
• Synthesis and Biological Evaluation of Dihydroisoquinoline-2(1H)- Carbothioamide Derivatives as TRPV1 Antagonists
  作者：Hai Qian、Wei Chen、Xiaoyan Zhang、Huibin Zhang、Jinpei Zhou、Wenlong Huang、Jing Jin、Dongyan Dai

  DOI：10.2174/157018010790945797

  日期：2010.5.1

  TRPV1 receptor is an important analgesia target. Its antagonists are expected to prevent pain perception by blocking the receptor directly. In this letter, eight dihydroisoquinoline-2(1H)-carbothioamide derivatives were designed and synthesized as TRPV1 antagonists. The benzene ring was modified with different substitutional groups. Preliminary biological tests suggested that the new compounds exhibited TRPV1 antagonist activity and different analgesia effects, some of which were promising as analgesia drugs.

  TRPV1受体是一个重要的镇痛靶点，其拮抗剂有望通过直接阻断受体来预防疼痛感知。在本文中，我们设计并合成了8种二氢异喹啉-2(1H)-硫代酰胺衍生物作为TRPV1拮抗剂，并对苯环进行了不同的取代基修饰。初步的生物测试表明，这些新化合物显示出TRPV1拮抗活性，并具有不同的镇痛效果，其中一些有望成为镇痛药物。
• Na₂S₂O₈-mediated efficient synthesis of isothiocyanates from primary amines in water
  作者：Zhicheng Fu、Wenhao Yuan、Ning Chen、Zhanhui Yang、Jiaxi Xu

  DOI：10.1039/c8gc02261e

  日期：——

  We have developed two green, practical, and efficient procedures, including a one-pot one, to synthesize isothiocyanates from amines and carbon disulfide via desulfurization with sodium persulfate. Water is used as the solvent. Basic conditions are necessary for good chemoselectivity for isothiocyanates. Structurally diverse linear and branched alkyl amines and aryl amines are readily converted to isothiocyanates

  我们已经开发了两种绿色，实用且有效的方法，包括一锅法，可通过胺和二硫化碳通过胺合成异硫氰酸酯。用过硫酸钠脱硫。使用水作为溶剂。为了使异硫氰酸酯具有良好的化学选择性，必须具备碱性条件。通过两种方法，结构令人满意的直链和支链烷基胺和芳基胺很容易以令人满意的产率转化为异硫氰酸酯。卤素，苄基CH键，甲硫基，硝基，酯，烯基，富电子或不足的（杂）芳基，乙炔基，甚至酚和醇羟基均被很好地耐受。在水中一锅法也可用于从手性胺制备手性异硫氰酸酯，以及用游离氨基修饰生物活性结构。在大规模制备中，开发了独立于柱色谱法的简单实用的纯化方法。
• CuBr₂ mediated synthesis of 2-Aminothiazoles from dithiocarbamic acid salts and ketones
  作者：Baohua Zhang、Lanxiang Shi

  DOI：10.1080/10426507.2019.1633316

  日期：2019.12.2

  Abstract In a one-pot procedure, CuBr2 has been used as a efficient desulfurizing agent in the synthesis of 2-aminothiazoles by the condensation of in situ-generated 1-substituted thioureas from their dithiocarbamic acid salts, with in situ-generated α-bromoketones from ketones. All reactions were carried out under optimized reaction conditions and gave the target products in 61–95% yield.

  摘要 在一锅法中，CuBr2 已被用作一种有效的脱硫剂，用于通过原位生成的二硫代氨基甲酸盐的 1-取代硫脲与原位生成的 α-溴酮缩合合成 2-氨基噻唑。从酮。所有反应均在优化的反应条件下进行，目标产物的产率为 61-95%。