N-(2-methoxybenzyl)benzo[d]thiazol-2-amine | 27468-51-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并噻唑类
• 英文名称: N-(2-methoxybenzyl)benzo[d]thiazol-2-amine
• 英文别名: N-(2-methoxybenzyl)benzothiazol-2-amine；N-2-methoxybenzylbenzothiazol-2-amine；N-[(2-methoxyphenyl)methyl]-1,3-benzothiazol-2-amine
• CAS: 27468-51-5
• 化学式: C₁₅H₁₄N₂OS
• 分子量: 270.355
• InChiKey: IEERERFNJOYYFV-UHFFFAOYSA-N

物化性质

• 沸点：
  428.4±47.0 °C(Predicted)
• 密度：
  1.284±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.2
• 重原子数：
  19
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.13
• 拓扑面积：
  62.4
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  邻甲氧基苄胺 、 2-氯苯并噻唑 在 copper(l) iodide 、 potassium carbonate 作用下， 以 二甲基亚砜 为溶剂， 反应 3.0h， 以29%的产率得到N-(2-methoxybenzyl)benzo[d]thiazol-2-amine
  参考文献：
  名称：

  通往2-氨基噻唑的便捷且可靠的途径：氟噻唑的钯催化与铜催化胺化反应

  摘要：

  AbstractTwo efficient methods for the amination of 2‐halothiazoles are presented here. A first protocol requires a Pd/L system. Several 2‐aminothiazoles were synthesized under optimized conditions and isolated in good yields. The first palladium‐catalyzed CN coupling reactions between 2‐halothiazoles and primary alkylamines are presented. In a second part, ligand‐free copper‐catalyzed aminations of 2‐halothiazoles by alkylamines and aniline in a green solvent have been developed. The protocol is very effective for primary and secondary amines and perfectly tolerates the presence of another halide moiety on the 2‐halothiazole. The reaction occurs under the assistance of microwave irradiation, which drastically decreases the reaction time. The reaction leads to the formation of 2‐aminothiazoles, key molecules in pharmaceutical research.magnified image

  DOI：

  10.1002/adsc.201300591

文献信息

• Structure-dependent tautomerization induced catalyst-free autocatalyzed N-alkylation of heteroaryl amines with alcohols
  作者：Shuangyan Li、Xiaohui Li、Qiang Li、Qiaochao Yuan、Xinkang Shi、Qing Xu

  DOI：10.1039/c4gc02542c

  日期：——

  Catalyst-free autocatalyzedN-alkylation of heteroarylamines with alcohols is achieved by tautomerization-induced ready generation of carbonyl intermediates from alcoholsviaTM-free MPV–O reaction.

  无需催化剂的自催化杂环胺与醇的N-烷基化是通过醇经酮互变引发的易生成羰基中间体实现的，通过无铁催化的MPV-O反应。
• 一种杂芳胺与胺反应合成取代杂芳胺的方法
  申请人：温州大学

  公开号：CN106565631B

  公开（公告）日：2018-11-30

  本发明公开了一种杂芳胺与胺反应合成取代杂芳胺的方法，以无机碱为促进剂，杂芳胺与胺直接进行脱氨气的烷基化反应得到N‑取代杂芳胺衍生物，反应温度为130～200℃，反应时间为24‑48小时，副产物为氨气；此技术方案，使用无机碱为促进剂、廉价易得的胺类为烷基化试剂，在氮气保护、密封、无溶剂条件下，杂芳胺与胺进行脱氨气的N‑烷基化反应可直接合成得到N‑取代杂芳胺衍生物。该反应方法直接，条件简单，易于操作，副产物为氨气，污染小，可回收利用。
• Laccase-Catalysed Homocoupling of Primary Aromatic Amines towards the Biosynthesis of Dyes
  作者：Ana Catarina Sousa、Lígia O. Martins、M. Paula Robalo

  DOI：10.1002/adsc.201300501

  日期：2013.10.11

  AbstractColoured disubstituted benzoquinonimine trimeric structures are obtained as main reaction products of the oxidation of p‐electron donor primary aromatic amines using two different laccases, CotA‐laccase from Baccilus subtilus and TvL from Trametes versicolor. These orange‐red to purple products, presenting high molar extinction coefficients, presumably result from oxidative homocoupling reactions, through the formation of NC bonds at positions 2 and 5, of the laccase oxidised intermediate as showed in the proposed oxidative pathway. The product of 1,4‐phenylenediamine is shown to be the trimer known as Bandrowski’s base which has an established role in hair and fur dyeing. Our results also show that the occurrence and/or rates of oxidation of aromatic amines are strongly dependent on the presence of p‐electron releasing substituents in the aromatic ring and are independent on the properties of the enzyme used. Overall our data contribute for (i) understanding key features of laccase reactivity with p‐substituted aromatic amines and (ii) establishing enzymatic processes that lead to the synthesis of coloured bio‐products under mild conditions with potential impact in the cosmetic and dye industries.magnified image
• Convenient and Reliable Routes Towards 2-Aminothiazoles: Palladium-Catalyzed<i>versus</i>Copper-Catalyzed Aminations of Halothiazoles
  作者：Stéphanie Toulot、Timo Heinrich、Frédéric R. Leroux

  DOI：10.1002/adsc.201300591

  日期：2013.11.11

  AbstractTwo efficient methods for the amination of 2‐halothiazoles are presented here. A first protocol requires a Pd/L system. Several 2‐aminothiazoles were synthesized under optimized conditions and isolated in good yields. The first palladium‐catalyzed CN coupling reactions between 2‐halothiazoles and primary alkylamines are presented. In a second part, ligand‐free copper‐catalyzed aminations of 2‐halothiazoles by alkylamines and aniline in a green solvent have been developed. The protocol is very effective for primary and secondary amines and perfectly tolerates the presence of another halide moiety on the 2‐halothiazole. The reaction occurs under the assistance of microwave irradiation, which drastically decreases the reaction time. The reaction leads to the formation of 2‐aminothiazoles, key molecules in pharmaceutical research.magnified image