2-(p-bromophenyl)-4,5-dimethyl-3,6-dihydro-1,2-oxazine | 105207-06-5

• 分子结构分类: 有机化合物 - 苯类化合物 - N-苯基羟胺
• 英文名称: 2-(p-bromophenyl)-4,5-dimethyl-3,6-dihydro-1,2-oxazine
• 英文别名: 2-(4-Bromophenyl)-4,5-dimethyl-3,6-dihydrooxazine；2-(4-bromophenyl)-4,5-dimethyl-3,6-dihydrooxazine
• CAS: 105207-06-5
• 化学式: C₁₂H₁₄BrNO
• 分子量: 268.153
• InChiKey: NSCKLHQCSDJKAU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  15
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  12.5
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  1-溴-4-亚硝基苯 、 2,3-二甲基-1,3-丁二烯 在 lithium perchlorate 作用下， 以 丙酮 为溶剂， 生成 2-(p-bromophenyl)-4,5-dimethyl-3,6-dihydro-1,2-oxazine
  参考文献：
  名称：

  无机高氯酸盐和周环反应。IV。1通过特定的阳离子-底物相互作用或通过增加的内部压力来提高速率？

  摘要：

  在几种无机高氯酸盐-有机溶剂溶液中研究了Diels-Alder和烯反应的动力学行为。观察到的速率加​​速是特定溶质阳离子相互作用或介质内部压力增加的结果，具体取决于基材，溶剂和金属阳离子。

  DOI：

  10.1016/0040-4020(95)00507-5

文献信息

• Synthesis of 3,6-Dihydro-2<i>H</i>-[1, 2]-Oxazines from Nitroarenes and Conjugated Dienes, Catalyzed by Palladium/Phenanthroline Complexes and Employing Phenyl Formate as a CO Surrogate
  作者：Mohamed A. EL-Atawy、Dario Formenti、Francesco Ferretti、Fabio Ragaini

  DOI：10.1002/cctc.201801223

  日期：2018.10.23

  Palladium/phenanthroline catalyzed reduction of nitroarenes by in situ‐generated carbon monoxide, from the decomposition of phenyl formate, affords the corresponding nitrosoarenes. The latter are trapped by conjugated dienes to give the corresponding 3,6‐dihydro‐2H‐[1, 2]‐oxazines (hetero Diels‐Alder adducts). Many functional groups are well tolerated. Yields are higher than those obtainable by any

  钯/菲咯啉通过原位生成的一氧化碳，从甲酸苯基酯的分解中催化还原硝基芳烃，得到相应的亚硝基芳烃。后者被共轭二烯捕获，得到相应的3,6-dihydro-2 H- [1,2]-恶嗪（杂Diels-Alder加合物）。许多功能组的耐受性良好。产率高于通过任何先前报道的方法可获得的产率，包括二烯与纯亚硝基芳烃的直接反应。该反应可在单个标准玻璃压力管中进行，而无需高压釜或高压CO管线。
• Solvent effect as the result of frontier molecular orbital interaction. V. Diels-Alder with heterodienophiles: a unified approach to the solvent effect of the Diels-Alder reactions
  作者：G. Desimoni、G. Faita、P.P. Righetti、L. Toma

  DOI：10.1016/s0040-4020(01)90093-6

  日期：1990.1

  The solvent effect of Diels-Alder (D.A.) reactions with heterodienophiles was measured in several solvents.

  在几种溶剂中测量了Diels-Alder（DA）与异二烯亲和性反应的溶剂作用。
• Catalysis with inorganic cations. 2. The effect of some perchlorates on Diels-Alder reaction rates
  作者：Adele Casaschi、Giovanni Desimoni、Giuseppe Faita、Anna Gamba Invernizzi、Simonetta Lanati、PierPaolo Righetti

  DOI：10.1021/ja00071a010

  日期：1993.9

  of sodium, lithium, barium, and magnesium perchlorate in acetone solution on the rates of different Diels-Alder reactions were kinetically investigated, 13 C-NMR spectroscopy being used as a tool to infer the mechanism of coordination of the solvated cations acting as catalysts. The Diels-Alder reactions, whose rates increase with increasing electrophilic character of the solvent, are strongly accelerated

  钠、锂、钡和镁在丙酮溶液中对不同 Diels-Alder 反应速率的影响进行了动力学研究，13 C-NMR 光谱被用作推断溶剂化阳离子的配位机制的工具催化剂。Diels-Alder 反应的速率随着溶剂亲电特性的增加而增加，在金属阳离子的存在下强烈加速。阳离子活性的顺序，Mg 2+ >Ba 2+ ≥Li + >Na + ，与它们各自的电荷：半径比的顺序平行。以亲核或非特异性溶剂效应为特征的 Diels-Alder 反应对任何金属阳离子的存在几乎不敏感，因为它不能充当亲电子试剂
• Inorganic perchlorates and pericyclic reactions. IV. 1 Rate enhancement by specific cation-substrate interaction or by increased internal pressure?
  作者：Giuseppe Faita、PierPaolo Righetti

  DOI：10.1016/0040-4020(95)00507-5

  日期：1995.8

  The kinetic behaviour of Diels-Alder and ene reactions was investigated in several inorganic perchlorate-organic solvent solutions. The observed rate accelerations are the result either of specific solute-cation interactions or of the increased internal pressure of the media, depending on substrates, solvents, and metal cations.

  在几种无机高氯酸盐-有机溶剂溶液中研究了Diels-Alder和烯反应的动力学行为。观察到的速率加​​速是特定溶质阳离子相互作用或介质内部压力增加的结果，具体取决于基材，溶剂和金属阳离子。