3-tosyl-1,2,3,4-tetrahydroquinazoline | 1458712-46-3

• 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: 3-tosyl-1,2,3,4-tetrahydroquinazoline
• 英文别名: 3-(4-methylphenyl)sulfonyl-2,4-dihydro-1H-quinazoline
• CAS: 1458712-46-3
• 化学式: C₁₅H₁₆N₂O₂S
• 分子量: 288.37
• InChiKey: SUUAJTPRMPCLKT-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  20
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  57.8
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  rac-2-(3-tosyl-1,2,3,4-tetrahydroquinazolin-2-yl)quinolin-8-ol 在 水 、 palladium diacetate 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 反应 24.0h， 生成 3-tosyl-1,2,3,4-tetrahydroquinazoline
  参考文献：
  名称：

  Serendipitous formation of 3-tosyl-1,2,3,4-tetrahydroquinazoline

  摘要：

  通过实验和计算研究阐明了 Pd(LBS)·3H2O 的甲醇母液中 3-甲苯磺酰基-1,2,3,4-四氢喹唑啉的形成过程，其中 LBS 是亚胺配体 N- 的双阴离子形式{2-[(8-羟基喹啉-2-基)亚甲基氨基]苄基}-4-甲基苯磺酰胺。实验研究表明，四氢喹唑啉是由2-甲苯磺酰氨基甲基苯胺与甲醛缩合而得，甲醛分别来自亚胺配体LBS的酸催化水解和甲醇的金属介导的有氧氧化。计算研究揭示了反应途径中的相关中间体和关键步骤。

  DOI：

  10.1039/c3nj00658a

文献信息

• Dual role of 2-tosylaminomethylaniline as a ligand and a nucleophile in the copper-mediated oxidation of methanol
  作者：Jesus Sanmartín-Matalobos、Ana M. García-Deibe、Lucía Briones-Miguéns、Concepcion González-Bello、Cristina Portela-García、Matilde Fondo

  DOI：10.1039/c3dt52460d

  日期：——

  Some reactivity in the oxidation of methanol to formaldehyde has been spectroscopically detected on the methanolic mother liquors of a copper(II) complex of a Schiff base ligand derived from the condensation of 8-hydroxyquinoline-2-carboxaldehyde and 2-tosylaminomethylaniline. An investigation has shown that 2-tosylaminomethylaniline (HATS) plays a dual role in the oxidative process acting as a N-donor ligand and reacting in situ with formaldehyde, which leads to 3-tosyl-1,2,3,4-tetrahydroquinazoline (1). This was characterized by using both spectroscopic and X-ray diffraction techniques. The influence of 8-hydroxyquinoline derivatives, water and ligand stoichiometry on the yield of 1 was studied.

  在甲醇母液中通过光谱法检测到一些甲醇氧化生成甲醛的反应活性，这些母液来自于一个铜(II)配合物，其配体是一种席夫碱，由8-羟基喹啉-2-醛和2-甲苯磺酰胺甲基苯胺缩合而成。研究表明，2-甲苯磺酰胺甲基苯胺（HATS）在氧化过程中发挥双重作用，既作为N供体配体，又能在原位与甲醛反应，生成3-甲苯磺酰基-1,2,3,4-四氢喹唑啉（1）。这一过程通过光谱学和X射线衍射技术进行了表征。此外，还研究了8-羟基喹啉衍生物、水和配体配比对产物1产率的影响。
• Serendipitous formation of 3-tosyl-1,2,3,4-tetrahydroquinazoline
  作者：Jesus Sanmartín-Matalobos、Ana M. García-Deibe、Lucía Briones-Miguéns、Emilio Lence、Concepcion González-Bello、Cristina Portela-García、Matilde Fondo

  DOI：10.1039/c3nj00658a

  日期：——

  Both experimental and computational studies were undertaken to elucidate the formation process of 3-tosyl-1,2,3,4-tetrahydroquinazoline from methanolic mother liquors of Pd(LBS)·3H2O, where LBS is the dianionic form of the imine ligand N-2-[(8-hydroxyquinolin-2-yl)methyleneamino]benzyl}-4-methylbenzenesulfonamide. Experimental studies have shown that the tetrahydroquinazoline is obtained by condensation of 2-tosylaminomethylaniline and formaldehyde, which come from the acid-catalyzed hydrolysis of the imine ligand LBS and metal-mediated aerobic oxidation of methanol, respectively. Computational studies have revealed relevant intermediates and key steps in the reaction pathway.

  通过实验和计算研究阐明了 Pd(LBS)·3H2O 的甲醇母液中 3-甲苯磺酰基-1,2,3,4-四氢喹唑啉的形成过程，其中 LBS 是亚胺配体 N- 的双阴离子形式2-[(8-羟基喹啉-2-基)亚甲基氨基]苄基}-4-甲基苯磺酰胺。实验研究表明，四氢喹唑啉是由2-甲苯磺酰氨基甲基苯胺与甲醛缩合而得，甲醛分别来自亚胺配体LBS的酸催化水解和甲醇的金属介导的有氧氧化。计算研究揭示了反应途径中的相关中间体和关键步骤。
• Tuning the ring-chain tautomerism of a tetrahydroquinazoline/Schiff base system with unexpected methanol oxidation
  作者：Jesús Sanmartín-Matalobos、Cristina Portela-García、Ana M. García-Deibe、Matilde Fondo、Lucía Briones-Miguéns

  DOI：10.1016/j.poly.2013.08.034

  日期：2013.11

  The ring-chain tautomerism of a tetrahydroquinazoline/Schiff base (H2Lgrin/H2Lchain) system can be controlled by metal coordination through varying ligand stoichiometry of the reaction H2L + M-2(+) [H2Lring: 2-(3-tosyl-1,2,3,4-tetrahydroquinazolin-2-yl)quinolin-8-ol; H2Lchain: N-(2-[(8-hydroxyquinolin-2-yl) methyleneamino]benzyl}-4-methylbenzenesulphonamide and M: Co2+ and Cd2+]. The ring tautomer H2Lring undergoes a ring-opening reaction upon formation of dinuclear complexes M-2(L-chain)(2), while Co2+ and Cd2+ stabilise the tetrahydroquinazoline ligand in their mononuclear complexes M(HLring)(2). The detection of 3-tosyl-1,2,3,4-tetrahydroquinazoline on the methanolic mother liquors of Co-2(L-chain)(2) revealed the acid-catalysed hydrolysis of the Schiff base ligand and the cobalt-mediated aerobic oxidation of methanol to formaldehyde. (C) 2013 Elsevier Ltd. All rights reserved.