4',5'-trans-5-hydroxymethyl-3,5-diphenyl-2-isoxazoline

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 4',5'-trans-5-hydroxymethyl-3,5-diphenyl-2-isoxazoline
• 英文别名: trans-4-hydroxymethyl-3,5-diphenyl-4,5-dihydroisoxazole；trans-3,5-diphenyl-2-isoxazoline-4-methanol；[(4R,5S)-3,5-diphenyl-4,5-dihydro-1,2-oxazol-4-yl]methanol
• 化学式: C₁₆H₁₅NO₂
• 分子量: 253.301
• InChiKey: VILXTMZJLXFIIV-GOEBONIOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  19
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.19
• 拓扑面积：
  41.8
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  2-(4'R-4',5'-trans-3',5'-diphenyl-2'-isoxazoline-4'-carbonyl)-3-phenyl-l-menthopyrazole 在 L-Selectride 作用下， 以 四氢呋喃 为溶剂， 反应 0.5h， 以53%的产率得到4',5'-trans-5-hydroxymethyl-3,5-diphenyl-2-isoxazoline
  参考文献：
  名称：

  Diastereoselective 1,3-Dipolar Cycloaddition of 2-(a,b-Unsaturated) Acyl-3-phenyl-l-menthopyrazoles

  摘要：

  The 1,3-dipolar cycloadducts of N-(alpha,beta-unsaturated) acylpyrazoles (2) with benzonitrile oxide or nitrones were afforded in good yield. in the cases of nitrones, the addition of MgBr2 or ZnBr2 promoted the stereoselectivity as well as the acceleration of the reaction rate. In the reaction of 2f and 2g, the big jump on the diastereoselectivity was accomplished by the addition of MgBr2, and (3'S,4'R,5'S)-8 was obtained as optically pure form in over 90% yield. These isoxazolidinecarbonylpyrazoles were converted into azetidinones in moderate yield with the retention of their stereo structures.

  DOI：

  10.3987/com-96-s19

文献信息

• Microwave Accelerated Cycloaddition Reactions of Nitrile Oxides and Allylic Alcohols
  作者：Ta-Jung Lu、Gwo-Ming Tzeng

  DOI：10.1002/jccs.200000022

  日期：2000.2

  promoting the cycloaddition reactions of allyl alcohols with nitrile oxides using a domestic microwave oven and a focused monomode microwave reactor have demonstrated that not only was the reaction time substantially reduced, but also the reaction yields were significantly improved over the conventional stirred reactions. Microwave irradiation alters the regioselectivity of the cycloaddition reaction which

  使用家用微波炉和聚焦单模微波反应器应用微波促进烯丙醇与氧化腈的环加成反应表明，与传统的搅拌反应器相比，不仅反应时间显着缩短，而且反应收率显着提高反应。微波照射改变了环加成反应的区域选择性，这有利于非氢键导向的环加合物异恶唑啉 4。
• Cycloadditions of Nitrile Oxides to α,β-Unsaturated Aldehydes. Frontier Orbital Interactions and Secondary Orbital Interactions at Work in Determining Regiochemistry
  作者：Lucio Toma、Paolo Quadrelli、Giancarlo Perrini、Remo Gandolfi、Cristiana Di Valentin、Antonino Corsaro、Pierluigi Caramella

  DOI：10.1016/s0040-4020(00)00356-2

  日期：2000.6

  oxides to crotonaldehyde and cinnamaldehyde has been determined and is dictated by frontier orbital interactions and secondary orbital interactions as well. In cycloadditions to α,β-unsaturated compounds the directive effect of the frontier orbital interactions can be diverted by steric drifts and secondary orbital interactions.

  已经确定了腈氧化物与巴豆醛和肉桂醛的环加成物的区域化学，并且也由边界轨道相互作用和次级轨道相互作用决定。在α，β-不饱和化合物的环加成反应中，前沿轨道相互作用的定向效应可通过空间漂移和次级轨道相互作用来转移。
• Diastereoselective 1,3-Dipolar Cycloaddition of 2-(a,b-Unsaturated) Acyl-3-phenyl-l-menthopyrazoles
  作者：Choji Kashima、Katsumi Takahashi、Iwao Fukuchi、Kiyoshi Fukusaka

  DOI：10.3987/com-96-s19

  日期：——

  The 1,3-dipolar cycloadducts of N-(alpha,beta-unsaturated) acylpyrazoles (2) with benzonitrile oxide or nitrones were afforded in good yield. in the cases of nitrones, the addition of MgBr2 or ZnBr2 promoted the stereoselectivity as well as the acceleration of the reaction rate. In the reaction of 2f and 2g, the big jump on the diastereoselectivity was accomplished by the addition of MgBr2, and (3'S,4'R,5'S)-8 was obtained as optically pure form in over 90% yield. These isoxazolidinecarbonylpyrazoles were converted into azetidinones in moderate yield with the retention of their stereo structures.