| 203790-23-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯二氮卓类
• CAS: 203790-23-2
• 化学式: C₁₃H₁₄N₂O₄
• 分子量: 262.265
• InChiKey: CKZLCIGLXNAHOW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.89
• 重原子数：
  19.0
• 可旋转键数：
  3.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  81.47
• 氢给体数：
  1.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  丁烯酮 、 生成 (1-Acetyl-5-oxo-1,2,4,5,6,10b-hexahydro-3-oxa-3a,6-diaza-benzo[e]azulen-4-yl)-acetic acid ethyl ester
  参考文献：
  名称：

  The synthesis of 1,2,7,11b-Tetrahydroisoxazolo[2,3-d][1,4]benzodiazepin-6(5H)-ones and 1,3,3a,9b-tetrahydroisoxazolo[4,3-c]quinolin-4(5H)-ones

  摘要：

  The reaction of various ethyl 3-[[2-(1-hydroxyiminoalkyl)phenyl]carbamoyl]acrylates (2) with electron deficient olefins proceeds via a sequential dipole formation, dipolar cycloaddition sequence to furnish the tetrahydroisoxazolo[2,3-d][1,4]benzodiazepin-6(5H)-ones and tetrahydroisoxazolo[4,3-c]quinolin-4(5H) (4) and (6). The product distribution reflects the nature of the reacting olefin and the position and extent of substitution on the acrylate moiety.

  DOI：

  10.1016/0040-4039(95)01523-x
• 作为产物：
  描述：

  在 吡啶 作用下， 以 甲苯 为溶剂， 以78%的产率得到
  参考文献：
  名称：

  Steric control of reactivity: formation of oximes, benzodiazepinone N-oxides and isoxazoloquinolinones

  摘要：

  与氢氧胺反应的烯烃羰基化合物1可以形成肟2、苯二氮杂类N-氧化物3或异噁唑喹啉酮5。反应的产物取决于末端烯烃取代基R3的电子性质，以及取代基R1、R2和R4的空间填充能力。当烯烃中心电子贫乏（R3 = CO2Et）时，酮羰基化合物仅能转化为双环硝酮3，而醛对骨架结构的微小变化更加敏感，能够生成肟2、三环化合物5或两者的混合物。对于醛和酮底物，当烯烃中心带有芳基取代基（R3 = Ph）时，反应的主要产物是相应的肟，经过热激活后转化为三环异噁唑喹啉酮。

  DOI：

  10.1039/a707857i

文献信息

• Nitrogen containing heterocycles from aldoximes; a one-pot route to isoxazolobenzodiazepinones, N-substituted and N-unsubstituted isoxazoloquinolinones
  作者：Frances Heaney、Sharon Bourke

  DOI：10.1039/a707078k

  日期：——

  The aldoximes 1 in the presence of electron poor olefins react to form either the 5,6,7-tricyclic isoxazolobenzodiazepinone 3 or the 5,6,6-tricyclic isoxazoloquinolinone 5 ring skeleton. In each case the ring system formed depends on the relative electrophilicity of the added and internal olefin. The oximes 1a,b,c react with N-methylmaleimide, methyl acrylate or phenyl vinyl sulfone to afford the corresponding regioisomeric isoxazolobenzodiazepinones by a tandem intramolecular dipole formation–intermolecular cycloaddition sequence. With the more electrophilic olefin, methyl vinyl ketone, intermolecular nitrone generation precedes intramolecular cycloaddition and the isoxazoloquinolinone skeleton results and for each oxime reaction proceeds smoothly in a regio- and stereo-specific manner. Steric control of chemoreactivity is observed with the ring or chain substituted aldoximes 1d,e,f. These oximes react in the presence of phenyl vinyl sulfone to give the isoxazolobenzodiazepines 15 and 16 together with varying quantities of the N-unsubstituted isoxazoloquinolines 14. The latter arise via an oxime–nitrone-cycloaddition sequence, in each case the cycloaddition proceeds in a regio- and stereo-specific manner. The oximes 1d,e,f react with methyl vinyl ketone to give single regio- and stereo-isomers of the N-unsubstituted and -substituted isoxazoloquinolinones 14 and 17. The high degree of chemo-, regio- and stereo-selectivity with which the one-pot reaction of the oximes 1 with electron poor olefins proceeds represents a convenient method for the construction of the title tricyclic molecular frameworks.

  醛肟1在电子贫烯烃存在的情况下，会形成5,6,7-三环异恶唑苯并二氮杂卓酮3或5,6,6-三环异恶唑喹啉酮5环骨架。在每种情况下，形成的环系统取决于所添加烯烃和内部烯烃的相对亲电性。醛肟1a,b,c与N-甲基马来酰亚胺、甲基丙烯酸甲酯或苯基乙烯基砜反应，通过串联分子内偶极形成-分子间环加成序列，得到相应的区域异构体异恶唑苯并二氮杂卓酮。对于亲电性更强的烯烃甲基乙烯基酮，分子间硝酮生成先于分子内环加成，形成异恶唑喹啉酮骨架，每种醛肟反应都以特定区域和立体方式顺利进行。环或链取代醛肟1d,e,f的化学活性受空间