5-chloro-3,6-diphenyl-2(H)-1,4-oxazin-2-one | 282537-68-2

• 分子结构分类: 有机化合物 - 有机卤素化合物 - 芳基卤化物
• 英文名称: 5-chloro-3,6-diphenyl-2(H)-1,4-oxazin-2-one
• 英文别名: 5-Chloro-3,6-diphenyl-1,4-oxazin-2-one；5-chloro-3,6-diphenyl-1,4-oxazin-2-one
• CAS: 282537-68-2
• 化学式: C₁₆H₁₀ClNO₂
• 分子量: 283.714
• InChiKey: VICGAZPYQDXPNY-UHFFFAOYSA-N

物化性质

• 熔点：
  146-149 °C
• 沸点：
  407.3±55.0 °C(Predicted)
• 密度：
  1.27±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4
• 重原子数：
  20
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  38.7
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  5-chloro-3,6-diphenyl-2(H)-1,4-oxazin-2-one 在 lithium aluminium tetrahydride 、 sodium acetate 、 sodium cyanoborohydride 、 溶剂黄146 作用下， 以 四氢呋喃 、 水 、 甲苯 为溶剂， 反应 28.0h， 生成 1,2,3,4,5,6-hexahydro-5α-hydroxy-2β,5β-diphenyl-2α-pyridinemethanol
  参考文献：
  名称：

  Stereoselective Transformation of 2H-1,4-Oxazin-2-ones into 2,(2),5,5-Tri- and Tetrasubstituted Analogues of cis-5-Hydroxy-2-piperidinemethanol and cis-5-Hydroxy-6-oxo-2-piperidinecarboxylic Acid

  摘要：

  2,(2),5,5-Tri- and tetrasubstituted analogues of 5-hydroxy-2-piperidinemethanol and 5-hydroxy-6-oxo-2-piperidinecarboxylic acid have been prepared via Diels-Alder reaction of 3-substituted 2H-1,4-oxazin-2-ones with ethene followed by functional group transformation of the resulting imidoyl chloride and lactone groups. Some of the 2-piperidinemethanol products are converted further into potential substance P antagonists. (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(00)00193-9
• 作为产物：
  描述：

  扁桃腈 在 四(三苯基膦)钯 三甲胺盐酸盐 作用下， 以 氯苯 、 甲苯 为溶剂， 反应 72.0h， 生成 5-chloro-3,6-diphenyl-2(H)-1,4-oxazin-2-one
  参考文献：
  名称：

  2（H）-1,4-Oxazin-2-ones的Diels-Alder环加成反应的研究

  摘要：

  各种在其3和6位带有一系列取代基的5-氯-2（H）-1,4-恶嗪-2-酮经历了Diels-Alder环加成反应，成为具有电子富集的2-azadiene组分，电子缺陷和电子中性的亲二烯体。这些反应以适度的区域选择性和立体选择性进行，以提供相对稳定且易于分离的桥连双环内酯环加合物。这些环加合物的化学操作提供了高度取代且功能丰富的哌啶。使用密度泛函理论（B3LYP / 6-31G *）通过计算研究了5-氯-2（H）-1,4-恶嗪-2-酮的环加成反应的区域和立体化学偏好。

  DOI：

  10.1021/jo051646i

文献信息

• 2( H )-1,4-Oxazin-2-ones as ambident azadienes
  作者：Kamyar Afarinkia、Akmal Bahar、Judi Neuss、Andrea Ruggiero

  DOI：10.1016/j.tetlet.2004.03.183

  日期：2004.5

  3.5-Dichloro-6-phenyl-2(H)-1,4-oxazin-2-one 3, 5-chloro-3,6-dimethyl-2(H)-1,4-oxazin-2-one 4, 5-chloro-6-methyl-3-phenyl-2(H)-1.4-oxazin-2-one 5 and 5-chloro-3.6-diplienyl-2(H)-1.4-oxazin-2-one 7, are ambident azadieries reacting efficiently and selectively with both electron rich and electron poor dienophiles. (C) 2004 Elsevier Ltd. All rights reserved.
• Stereoselective conversion of 2 H -1,4-oxazin-2-ones into 2,5,5-substituted piperidine-2-carboxamides and 2-methanamines and related octahydro-2 H -pyrido[1,2- a ]pyrazines, potential substance P antagonists
  作者：Joeri Rogiers、Xiujuan Wu、Suzanne Toppet、Frans Compernolle、Georges J Hoornaert

  DOI：10.1016/s0040-4020(01)00888-2

  日期：2001.10

  4-(Hetero)aryl-2-oxa-5-azabicyclo[2.2.2] octan-3-ones and 3,6-diones, formed via cycloaddition of 2H-1,4-oxazin-2-ones and ethene followed by functional group transformation, undergo lactone cleavage by reaction with amines to yield substituted 2-(hetero)aryl-5-hydroxy-2-piperidinecarboxamides. Subsequent reduction affords the corresponding 2-piperidinemethanamines. Both amide and amine compounds are of interest as potential Substance P antagonists. A detailed NMR study, supported by conformational calculations, of an octahydro-2H-pyrido[1,2-a]pyrazine analogue revealed the existence of a temperature and solvent dependent equilibrium mixture of transoid and cisoid invertomers. (C) 2001 Elsevier Science Ltd. All rights reserved.