2-苯基-4-亚哌并-2-噁唑啉-5-酮 | 6412-89-1

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 中文名称: 2-苯基-4-亚哌并-2-噁唑啉-5-酮
• 英文名称: 2-phenyl-4-piperonyliden-4H-oxazol-5-one
• 英文别名: 4-benzo[1,3]dioxol-5-ylmethylene-2-phenyl-4H-oxazol-5-one；2-Phenyl-4-piperonyliden-4H-oxazol-5-on；4-[(2H-1,3-benzodioxol-5-yl)methylidene]-2-phenyl-4,5-dihydro-1,3-oxazol-5-one；4-(1,3-benzodioxol-5-ylmethylidene)-2-phenyl-1,3-oxazol-5-one
• CAS: 6412-89-1
• 化学式: C₁₇H₁₁NO₄
• mdl: MFCD00022965
• 分子量: 293.279
• InChiKey: RKXHYEBOSSBZSH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  22
• 可旋转键数：
  2
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.06
• 拓扑面积：
  57.1
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  2-苯基-4-亚哌并-2-噁唑啉-5-酮 在 甲醇 、 sodium hydroxide 、 Pd-BaSO₄ 作用下， 生成 N-benzoyl-(R,S)-3,4-methylenedioxyphenylalanine methyl ester
  参考文献：
  名称：

  Kotschetkow et al., Zhurnal Obshchei Khimii, 1959, vol. 29, p. 68,73

  摘要：

  DOI：
• 作为产物：
  描述：

  3-benzo[1,3]dioxol-5-yl-2-benzoylamino-acrylic acid 在 乙酸酐 作用下， 生成 2-苯基-4-亚哌并-2-噁唑啉-5-酮
  参考文献：
  名称：

  Kropp; Decker, Chemische Berichte, 1909, vol. 42, p. 1188

  摘要：

  DOI：

文献信息

• An efficient synthesis of new class of pyrazolo[3,4-<i>b</i>]pyridine-6-one derivatives by a novel cascade reaction
  作者：Feng Shi、Junyong Zhang、Shujiang Tu、Runhong Jia、Yan Zhang、Bo Jiang、Hong Jiang

  DOI：10.1002/jhet.5570440506

  日期：2007.9

  A novel cascade reaction of 4-arylidene-2-phenyl-1,3-oxazol-5(4H)-one with 3-methyl-1-phenyl-1H-pyrazol-5-amine was described and a number of new pyrazolo[3,4-b]pyridine-6-one derivatives were synthesized. This new protocol has the advantages of shorter time, higher yields, and lower cost as well as easier operation.

  描述了一种新的4-亚芳基-2-苯基-1,3-恶唑-5（4 H）-与3-甲基-1-苯基-1 H-吡唑-5-胺的级联反应，许多新的合成了吡唑并[3,4- b ]吡啶-6-衍生物。该新协议的优点是时间更短，产量更高，成本更低以及操作更简便。
• Synthesis of<i>N</i>-(3-Arylmethyl-2-oxo-2,3-dihydroimidazo[1,2-<i>a</i>]pyridin-3-yl)benzamides
  作者：Shujiang Tu、Junyong Zhang、Runhong Jia、Bo Jiang、Yan Zhang、Changsheng Yao、Hong Jiang

  DOI：10.1246/cl.2007.222

  日期：2007.2

  A new series of imidazo[1,2-a]pyridin-2-one derivatives were synthesized by the reaction of 4-arylidene-2-phenyl-5(4H)-oxazolones and pyridin-2-amine under microwave irradiation in ethylene glycol. The starting materials were easily obtained and the operation was very convenient.

  一系列新的咪唑[1,2-a]吡啶-2-酮衍生物通过在乙二醇中以微波辐射反应4-芳亚胺-2-苯基-5(4H)-噁唑酮与吡啶-2-胺合成。起始材料易于获得，操作非常方便。
• Amphiphilic allylation of arylidene-1,3-oxazol-5(4H)-one using bis-π-allylpalladium complexes: an approach to synthesis of cyclohexyl and cyclohexenyl α-amino acids
  作者：Afaf R. Genady、Hiroyuki Nakamura

  DOI：10.1039/c1ob05952a

  日期：——

  α-amino acids via palladium-catalyzed three-component assemblies followed by ring-closing metathesis (RCM) is described. The present catalytic reaction is successfully extended to substituted benzylidene azlactones 2a–j RCH=(1,3-oxazole): R = alkyl or aryl. The amphiphilic bis-allylation of these substrates has been achieved by replacing toxic allylstannanes with allyltrifluoroborate and the reaction

  一种有效的合成环己基和 环己烯基α-氨基通过酸 钯催化三组分组装，然后进行闭环复分解（RCM）。本催化反应成功地扩展到取代亚苄基内酯2a–j RCH =（1,3-恶唑）：R ＝烷基或芳基。这些底物的两亲性双烯丙基化已通过用三氟硼酸烯丙酯 反应顺利进行，得到相应的 1,7-二烯衍生品3a–j的收益率可以接受。使用第一代Grubbs催化剂得到的辛二烯的RCM可轻松获得立体定义的取代基环己烯高收率的7-11衍生物。酸水解恶唑酮7–10的环给出了受保护的氨基酸12–16。13和15的脱苯甲酰化分别以优异的产率提供了1-氨基-6-芳基-环己-3-烯羧酸17和18。此外，催化还原13得到相应的环己烷衍生物19可以去苯甲酰化得到1-氨基-2-苯基环己烯-1-羧酸（20）。通过X射线结构分析证实了化合物9、12和13的结构。这是产生大量环状α，α-二取代的极好方法α-氨基 酸。
• Synthesis, reactions and biological evaluation of some 1,2,4-triazine derivatives
  作者：A. K. Mansour、Mohga M. Eid、R. A. Hassan、A. Haemers、S. R. Pattyn、D. A. Vanden Berghe、L. Van Hoof

  DOI：10.1002/jhet.5570250146

  日期：1988.1

  react with hydrazine hydrate to give the corresponding 6-substituted benzyl-4-amino-2,3,4,5-tetrahydro-1,2,4-triazin-3,5-diones 10a-c. The biological evaluation of some of these triazines is described. All compounds were screened for antiviral, antibacterial, antimycobacterial, antifungal and antiyeast activity. No important biological activity was found.

  制备6-取代的苄基-4-苯基-3-硫代氧代2,3,4,5-四氢-1,2,4-三嗪-5-酮3a-d并将其转化为它们相应的3-甲硫基衍生物4a- d。化合物4a-d与水合肼的反应得到相应的4-氨基-3-苯胺基-4,5-二氢-1,2,4-三嗪-5-酮5a-d。合成6-取代的苄基-4-苯基-2,3,4,5-四氢-1,2,4-三嗪-3,5-二酮9a-c，并使其与水合肼反应，得到相应的6--取代的苄基-4-氨基-2,3,4,5-四氢-1,2,4-三嗪-3,5-二酮10a-c。描述了其中一些三嗪的生物学评估。筛选所有化合物的抗病毒，抗菌，抗分枝杆菌，抗真菌和抗酵母活性。没有发现重要的生物学活性。
• A Novel Reaction of 4-(Arylmethylene)-2-phenyloxazol-5(4H)-ones with Pyridin-2-amine: Formation of 3-(Arylmethyl)-3-(benzoylamino)imidazo-[1,2-a]pyridin-2(3H)-ones
  作者：Shujiang Tu、Junyong Zhang、Runhong Jia、Yan Zhang、Bo Jiang、Feng Shi

  DOI：10.1055/s-2007-965898

  日期：2007.2

  A new series of imidazo[1,2-a]pyridin-2-one derivatives were synthesized by a novel reaction of 4-(arylmethylene)-2-phenyl­oxazol-5(4H)-one with pyridin-2-amine under microwave irradiation in ethylene glycol. The starting materials were easily obtained and the operation was convenient.

  一种新的咪唑并[pyridin-2-one]衍生物系列通过在乙二醇中使用微波辐射将4-(芳基亚甲基)-2-苯氧唑-5(4H)-酮与吡啶-2-胺的反应合成。起始材料易于获得，操作也很方便。