3,4-dihydro-2-phenylbenzo[f][1,4]oxazepin-5(2H)-one | 22217-08-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并恶嗪类
• 英文名称: 3,4-dihydro-2-phenylbenzo[f][1,4]oxazepin-5(2H)-one
• 英文别名: 2-phenyl-3,4-dihydro-1,4-benzoxazepin-5(2H)-one；2-phenyl-3,4-dihydrobenzo[f ][1,4]oxazepin-5(2H)-one；2-phenyl-3,4-dihydro-2H-benzo[f][1,4]oxazepin-5-one；2-phenyl-3,4-dihydro-2H-1,4-benzoxazepin-5-one
• CAS: 22217-08-9
• 化学式: C₁₅H₁₃NO₂
• 分子量: 239.274
• InChiKey: UADLSBYXTMUWIV-UHFFFAOYSA-N

物化性质

• 熔点：
  126-129 °C
• 沸点：
  489.5±45.0 °C(Predicted)
• 密度：
  1.185±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  18
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.13
• 拓扑面积：
  38.3
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  3,4-dihydro-2-phenylbenzo[f][1,4]oxazepin-5(2H)-one 以32%的产率得到
  参考文献：
  名称：

  LEVAI A.; BOGNAR R., ACTA CHIM. ACAD. SCI. HUNG., 1978, 97, NO 1, 77-83

  摘要：

  DOI：
• 作为产物：
  描述：

  2,3-dihydro-2-phenyl-5-trichloroacetoxy-1,4-benzoxazepine 在 水 作用下， 以85%的产率得到3,4-dihydro-2-phenylbenzo[f][1,4]oxazepin-5(2H)-one
  参考文献：
  名称：

  Litkei, Gy.; Patonay, T., Acta Chimica Hungarica, 1983, vol. 114, # 1, p. 47 - 56

  摘要：

  DOI：

文献信息

• Azido-Schmidt reaction for the formation of amides, imides and lactams from ketones in the presence of FeCl3
  作者：J.S. Yadav、B.V. Subba Reddy、U.V. Subba Reddy、K. Praneeth

  DOI：10.1016/j.tetlet.2008.05.113

  日期：2008.8

  Ketones undergo smooth rearrangement with TMSN3 in the presence of FeCl3 under extremely mild conditions to provide the corresponding amides, imides and lactams in good yields with high selectivity. This method is very useful for the preparation of a wide range of amides, imides and lactams from ketones. The use of FeCl3 makes this method simple, convenient and cost-effective.

  在极温和的条件下，在FeCl 3存在下，酮与TMSN 3进行平滑的重排，从而以高收率和高选择性提供相应的酰胺，酰亚胺和内酰胺。该方法对于从酮制备各种酰胺，酰亚胺和内酰胺非常有用。FeCl 3的使用使该方法简单，方便且具有成本效益。
• Oxazepines and Thiazepines, XXVII: Chemical Transformations of 2,3-Dihydro-2-phenyl-1,4-benzoxazepin-5(4H)-one
  作者：Albert Lévai、Zoltán Bálint

  DOI：10.1002/ardp.19933260204

  日期：——

  N‐Alkyl (2 ‐ 11) and N‐acyl (18 ‐ 30) derivatives of 2,3‐dihydro‐2‐phenyl‐1,4‐benzoxazepin‐5(4H)‐one (1) have been synthesized. 4‐Alkyl‐2,3‐dihydro‐2‐phenyl‐1,4‐benzoxazepin‐5(4H)‐thiones 12 ‐ 15 arose from compounds 2, 3, 5, and 6 with Lawesson's reagent. Bis‐[2,3‐dihydro‐2‐phenyl‐1,4‐benzoxazepin‐5(4H)‐onyl]‐alkanes 16 and 17 were prepared from 1 and dihaloalkanes.

  已经合成了 2,3-二氢-2-苯基-1,4-苯并恶氮杂-5 (4H) -one (1) 的 N-烷基 (2-11) 和 N-酰基 (18-30) 衍生物。4 - 烷基 - 2,3 - 二氢 - 2- 苯基 - 1,4 - 苯并恶氮杂 - 5 (4H) - 硫酮 12 - 15 由化合物 2、3、5 和 6 与劳森试剂产生。双-[2,3-二氢-2-苯基-1,4-benzoxazep​​ine-5 (4H) -onyl]-烷烃 16 和 17 由 1 和二卤代烷烃制备。
• Remodeling and Enhancing Schmidt Reaction Pathways in Hexafluoroisopropanol
  作者：Hashim F. Motiwala、Manwika Charaschanya、Victor W. Day、Jeffrey Aubé

  DOI：10.1021/acs.joc.5b02764

  日期：2016.2.19

  The effect of carrying out two variations of the Schmidt reaction with ketone electrophiles in hexafluoroisopropanol (HFIP) solvent has been studied. When TMSN3 is reacted with ketones in the presence of triflic acid (TfOH) promoter, tetrazoles are obtained as the major products. This observation is in contrast to established methods, which usually lead to amides or lactams arising from formal NH insertion

  研究了在六氟异丙醇（HFIP）溶剂中与酮亲电试剂进行Schmidt反应的两种变化的效果。当TMSN 3在三氟甲磺酸（TfOH）促进剂的存在下，使酮与酮反应，得到四唑为主要产物。该观察结果与已建立的方法相反，已建立的方法通常导致正式NH插入作为主要产物而产生酰胺或内酰胺。还报道了该反应的几个实例的全部产物概况，发现其包括机械上令人感兴趣的产物（例如，双环膨胀）。还发现在HFIP中使用TfOH促进剂可以促进羟烷基叠氮化物与酮的反应，与最初报道的方法相比，在亲核打开初始形成的亚胺醚后，内酰胺得到内酰胺的效率更高。
• Preparation of neuroprotective condensed 1,4-benzoxazepines by regio- and diastereoselective domino Knoevenagel–[1,5]-hydride shift cyclization reaction
  作者：László Tóth、Yan Fu、Hai Yan Zhang、Attila Mándi、Katalin E Kövér、Tünde-Zita Illyés、Attila Kiss-Szikszai、Balázs Balogh、Tibor Kurtán、Sándor Antus、Péter Mátyus

  DOI：10.3762/bjoc.10.272

  日期：——

  Condensed O,N-heterocycles containing tetrahydro-1,4-benzoxazepine and tetrahydroquinoline moieties were prepared by a regio- and diastereoselective domino Knoevenagel–[1,5]-hydride shift cyclization reaction of a 4-aryl-2-phenyl-1,4-benzoxazepine derivative obtained from flavanone. The relative configuration of products were determined by the correlation of ³J_H,H coupling data with the geometry of major conformers accessed by DFT conformational analysis. Separated enantiomers of the products were characterized by HPLC-ECD data, which allowed their configurational assignment on the basis of TDDFT-ECD calculation of the solution conformers. Two compounds showed neuroprotective activities against hydrogen peroxide (H₂O₂) or β-amyloid_25–35 (Aβ_25–35)-induced cellular injuries in human neuroblastoma SH-SY5Y cells in the range of those of positive controls.

  通过从黄烷酮中获得的4-芳基-2-苯基-1,4-苯并噁唑啉衍生物的区域和对映选择性Knoevenagel-[1,5]-氢移位环化反应，制备了含有四氢-1,4-苯并噁唑啉和四氢喹啉基团的浓缩O，N-杂环化合物。通过将3JHH偶合数据与DFT构象分析所访问的主要构象的几何形状相关联，确定了产物的相对构型。通过HPLC-ECD数据表征产物的分离对映体，基于溶液构象的TDDFT-ECD计算确定其构型。两种化合物在人类神经母细胞瘤SH-SY5Y细胞中对过氧化氢（H2O2）或β-淀粉样蛋白25-35（Aβ25-35）诱导的细胞损伤表现出神经保护活性，范围在正对照的范围内。
• Benzodiazepine analogues. Part 19.1H and13C NMR spectroscopic studies of 2-phenyl-1,4- and 1,5-benzoheterazepinethione derivatives
  作者：Malose J. Mphahlele、Perry T. Kaye

  DOI：10.1002/(sici)1097-458x(200003)38:3<207::aid-mrc595>3.0.co;2-6

  日期：2000.3

  Selected 1,4‐ and 1,5‐benzoheterazepinones, prepared by the Schmidt rearrangement of flavanone analogues, were converted to the corresponding thiolactam derivatives using phosphorus pentasulfide. The proton and carbon chemical shifts of the thiolactam derivatives are compared with those of their lactam precursors. Copyright © 2000 John Wiley & Sons, Ltd.

  选定的 1,4- 和 1,5-苯并杂氮杂酮，通过黄烷酮类似物的施密特重排制备，使用五硫化二磷转化为相应的硫内酰胺衍生物。将硫内酰胺衍生物的质子和碳化学位移与其内酰胺前体的质子和碳化学位移进行比较。版权所有 © 2000 John Wiley & Sons, Ltd.

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