2-(4-chlorophenyl)-6-phenyl-3,6-dihydro-2H-[1,2]oxazine | 92874-51-6

• 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-(4-chlorophenyl)-6-phenyl-3,6-dihydro-2H-[1,2]oxazine
• 英文别名: 2-(4-chloro-phenyl)-6-phenyl-3,6-dihydro-2H-[1,2]oxazine；2-(p-Chlorphenyl)-3-phenyl-3,6-dihydro-1,2-oxazin；6-Phenyl-2-(4-chlorphenyl)-3,6-dihydro-1,2-oxazin；2-(4-Chlorophenyl)-6-phenyl-3,6-dihydrooxazine
• CAS: 92874-51-6
• 化学式: C₁₆H₁₄ClNO
• 分子量: 271.746
• InChiKey: GITPNCOIVDTTTJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.6
• 重原子数：
  19
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  12.5
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  2-(4-chlorophenyl)-6-phenyl-3,6-dihydro-2H-[1,2]oxazine 在 copper(l) chloride 作用下， 以 乙腈 为溶剂， 以66 %的产率得到1-(4-chlorophenyl)-2-phenyl-1H-pyrrole
  参考文献：
  名称：

  使用甲酸作为 CO 替代物在二烯存在下还原硝基芳烃：通过 1,2-恶嗪两步合成 N-芳基吡咯

  摘要：

  使用甲酸作为 CO 替代物，将硝基芳烃脱氧为亚硝基芳烃，该反应由钯/菲咯啉络合物催化。亚硝基芳烃被共轭二烯捕获，得到 3,6-二氢-2H- [ 1,2]-恶嗪。然后使用 CuCl 作为催化剂将后者转化为N-芳基吡咯。该反应可以制备在 2 和 5 位上缺乏任何取代基的吡咯，而使用大多数吡咯合成方法很难生产这种吡咯。

  DOI：

  10.1002/ejoc.202300809
• 作为产物：
  描述：

  1-苯-1,3-丁二烯 、 对氯苯胺 在 MoO(O₂)(2,6-pyridinedicarboxylato-O,N,O')(HMPA) 双氧水 作用下， 反应 18.0h， 以78%的产率得到2-(4-chlorophenyl)-6-phenyl-3,6-dihydro-2H-[1,2]oxazine
  参考文献：
  名称：

  A Molybdenum-Catalyzed Oxidative System Forming Oxazines (Hetero-Diels−Alder Adducts) from Primary Aromatic Amines, Hydrogen Peroxide, and Conjugated Dienes

  摘要：

  The development of a new molybdenum-catalyzed procedure for the formation of oxazines-hetero-Diels-Alder adducts-from primary aromatic amines, hydrogen peroxide, and conjugated dienes is presented, The method is based on a molybdenum-peroxo complex, which in the presence of hydrogen peroxide as the terminal oxidant selectively catalyzes the oxidation of primary aromatic amines to the corresponding dienophilic nitroso compounds. The molybdenum-peroxo catalyst is under the present reaction conditions not reactive toward conjugated dienes and substituents attached to the aromatic nuclei of the primary aromatic amines. Several oxazines are synthezised following this new procedure using primary aromatic amines having either electron-withdrawing or electron-donating substituents and 1,3-cyclohexadiene as the standard diene. The scope of the new procedure is also demonstrated by the preparation of several oxazines using different alkyl- and phenyl-substituted conjugated dienes and 4-chloroaniline as precursor for the dienophile. Moderate diastereomeric excesses are found when the reaction is carried out with 1-(2-aminophenyl)-ethanol and 1,3-cyclohexadiene or (E)-1-phenyl-1,3-butadiene. The stereochemical and electronic factors governing the reaction course are briefly discussed.

  DOI：

  10.1021/jo9608127

文献信息

• Additionsreaktionen der nitrosogruppe—V
  作者：G. Kresze、J. Firl

  DOI：10.1016/s0040-4020(01)98558-8

  日期：1963.1

  1-Arylbutadienes add to p-chloronitrosobenzene to give, solely, 6-aryl-1,2-oxazines as 1:1 adducts. This orientation is followed regardless of the polar character of the p-substituent of the 1-arylbutadienes.

  1-芳基丁二烯加到对氯亚硝基苯中，仅以1：1的加合物形式得到6-芳基-1,2-恶嗪。无论1-芳基丁二烯的对位取代基的极性特征如何，都遵循该取向。
• A Molybdenum-Catalyzed Oxidative System Forming Oxazines (Hetero-Diels−Alder Adducts) from Primary Aromatic Amines, Hydrogen Peroxide, and Conjugated Dienes
  作者：Eval Rud Møller、Karl Anker Jørgensen

  DOI：10.1021/jo9608127

  日期：1996.1.1

  The development of a new molybdenum-catalyzed procedure for the formation of oxazines-hetero-Diels-Alder adducts-from primary aromatic amines, hydrogen peroxide, and conjugated dienes is presented, The method is based on a molybdenum-peroxo complex, which in the presence of hydrogen peroxide as the terminal oxidant selectively catalyzes the oxidation of primary aromatic amines to the corresponding dienophilic nitroso compounds. The molybdenum-peroxo catalyst is under the present reaction conditions not reactive toward conjugated dienes and substituents attached to the aromatic nuclei of the primary aromatic amines. Several oxazines are synthezised following this new procedure using primary aromatic amines having either electron-withdrawing or electron-donating substituents and 1,3-cyclohexadiene as the standard diene. The scope of the new procedure is also demonstrated by the preparation of several oxazines using different alkyl- and phenyl-substituted conjugated dienes and 4-chloroaniline as precursor for the dienophile. Moderate diastereomeric excesses are found when the reaction is carried out with 1-(2-aminophenyl)-ethanol and 1,3-cyclohexadiene or (E)-1-phenyl-1,3-butadiene. The stereochemical and electronic factors governing the reaction course are briefly discussed.
• Use of Formic Acid as a CO Surrogate for the Reduction of Nitroarenes in the Presence of Dienes: A Two‐Step Synthesis of <i>N</i>‐Arylpyrroles via 1,2‐Oxazines
  作者：Manar Ahmed Fouad、Francesco Ferretti、Simone Galiè、Fabio Ragaini

  DOI：10.1002/ejoc.202300809

  日期：2023.10.9

  Formic acid was employed as a CO surrogate to deoxygenate nitroarenes to nitrosoarenes, a reaction catalyzed by a palladium/phenanthroline complex. Nitrosoarenes, trapped by conjugated dienes, afforded 3,6-dihydro-2H-[1,2]-oxazines. The latter were then transformed into N-arylpyrroles employing CuCl as the catalyst. The reaction allows to prepare pyrroles lacking any substituent in the 2 and 5 positions

  使用甲酸作为 CO 替代物，将硝基芳烃脱氧为亚硝基芳烃，该反应由钯/菲咯啉络合物催化。亚硝基芳烃被共轭二烯捕获，得到 3,6-二氢-2H- [ 1,2]-恶嗪。然后使用 CuCl 作为催化剂将后者转化为N-芳基吡咯。该反应可以制备在 2 和 5 位上缺乏任何取代基的吡咯，而使用大多数吡咯合成方法很难生产这种吡咯。