2-tert-butyl-4-methylcarboxy-3,5-diphenyl-4-isoxazoline | 137578-85-9

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 肉桂酸及其衍生物
• 英文名称: 2-tert-butyl-4-methylcarboxy-3,5-diphenyl-4-isoxazoline
• 英文别名: methyl 2-tert-butyl-3,5-diphenyl-3H-1,2-oxazole-4-carboxylate
• CAS: 137578-85-9
• 化学式: C₂₁H₂₃NO₃
• 分子量: 337.419
• InChiKey: DBQNHKKBFUXWQL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.36
• 重原子数：
  25.0
• 可旋转键数：
  3.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  38.77
• 氢给体数：
  0.0
• 氢受体数：
  4.0

反应信息

• 作为产物：
  描述：

  (Z)-N-benzylidene-2-methylpropan-2-amine oxide 、 苯丙炔酸甲酯 以 四氢呋喃 为溶剂， 反应 1800.0h， 以32%的产率得到2-tert-butyl-4-methylcarboxy-3,5-diphenyl-4-isoxazoline
  参考文献：
  名称：

  Chan, Kin Shing, Journal of the Chemical Society. Perkin transactions I, 1991, # 4, p. 2602 - 2603

  摘要：

  DOI：

文献信息

• Chemistry of unsaturated arenetricarbonylchromium compounds 1. Reaction of (η6-arene)tricarbonylchromium complexes of nitrones with methyl phenylpropiolate
  作者：N. Yu. Zarovkina、E. V. Sazonova、A. N. Artemov、G. K. Fukin

  DOI：10.1007/s11172-014-0535-5

  日期：2014.4

  The reactions of nitrones of the composition (CO)3CrC6H5CH=N+(O−)R (R = Me, Ph, or But) with substituted acetylene were studied. The reactions proceed with high regioselectivity and give 4-isoxazolines (yields 50–60%). The composition and structures of these products were characterized by physicochemical methods. The reactions also afford (η6-benzaldehyde)tricarbonylchromium, coordinated Schiff bases

  研究了组成为 (CO)3CrC6H5CH=N+(O-)R（R = Me、Ph 或 But）的硝酮与取代乙炔的反应。该反应以高区域选择性进行并产生 4-异恶唑啉（产率 50-60%）。这些产物的组成和结构通过物理化学方法表征。该反应还提供（η6-苯甲醛）三羰基铬、配位的席夫碱和氧化偶氮衍生物作为起始硝酮的热分解产物。还研究了未配位硝酮与苯丙炔酸甲酯的反应。这些反应产生 4-异恶唑啉以及环状取代的异恶唑啉酮。
• Chromium and Tungsten Pentacarbonyl Groups as Reactivity and Selectivity Auxiliaries in [3 + 2] Cycloaddition of Alkynyl Fischer Carbene Complexes with N-Alkyl Nitrones
  作者：Kin Shing Chan、Ming Lok Yeung、Wai-kin Chan、Ru-Ji Wang、Thomas C. W. Mak

  DOI：10.1021/jo00111a036

  日期：1995.3

  Alkynyl Fischer carbene complexes were found to undergo chemoselective, regioselective, and rate-enhanced 1,3-dipolar cycloaddition with nitrones to give 2,3-dihydroisoxazole carbene complexes in excellent yields. These alkynyl complexes can serve as synthons for substituted propiolate esters since the metal pentacarbonyl group of the cycloadducts can be easily oxidatively removed with DMSO. The tungsten carbene complex 4b reacted with 3 different series of N-alkyl nitrones: N-tert-butyl 2a-f, N-methyl 1a-h and N-benzyl 3 to give cycloadducts 6a-f, 7a-h, and 8-9, respectively, while the chromium carbene complex 4a reacted only with N-tert-butyl nitrones 2a-g to give isolable cycloadducts 5a-g. The structure of N-methyl cycloadduct 7d has been established by a single-crystal X-ray analysis. The reactivity of N-alkyl nitrones toward carbene complexes was in the order: N-Me > N-Bn > N-(t)Bu. In addition, our results showed that the rate of cycloaddition reaction increased as the electron donating ability of para-substituent in N-tert-butyl nitrone 2a-f increased.
• Chan, Kin Shing, Journal of the Chemical Society. Perkin transactions I, 1991, # 4, p. 2602 - 2603
  作者：Chan, Kin Shing

  DOI：——

  日期：——