4-carbomethoxy-N-methyl-3-phenyl-4,5-dehydroisoxazolidine | 109787-19-1

• 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-carbomethoxy-N-methyl-3-phenyl-4,5-dehydroisoxazolidine
• 英文别名: 2-methyl-3-phenyl-4-carbomethoxy-4-isoxazoline；5-carbomethoxy-N-methyl-3-phenylisoxazoline；2-Methyl-3-phenyl-Δ⁴-isoxazolin-4-carbonsaeure-methylester；2-methyl-3-phenyl-2,3-dihydro-isoxazole-4-carboxylic acid methyl ester；methyl 2-methyl-3-phenyl-3H-1,2-oxazole-4-carboxylate
• CAS: 109787-19-1
• 化学式: C₁₂H₁₃NO₃
• 分子量: 219.24
• InChiKey: CJZVLFXBEKIIOZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  16
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  38.8
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  4-carbomethoxy-N-methyl-3-phenyl-4,5-dehydroisoxazolidine 在 间氯过氧苯甲酸 作用下， 以 二氯甲烷 为溶剂， 反应 3.0h， 以97%的产率得到3-phenyl-2-carbomethoxyacrolein
  参考文献：
  名称：

  Peracid oxidation of 4-isoxazolines as a method for the preparation of .alpha.,.beta.-unsaturated carbonyl compounds

  摘要：

  DOI：

  10.1021/jo00245a021
• 作为产物：
  描述：

  苯甲醛肟 在 cesium fluoride 作用下， 以 乙二醇二甲醚 为溶剂， 反应 12.0h， 生成 4-carbomethoxy-N-methyl-3-phenyl-4,5-dehydroisoxazolidine
  参考文献：
  名称：

  Silyl group transfer in the cycloaddition reactions of silyl iminium salts derived from aryl-substituted oximes

  摘要：

  DOI：

  10.1021/jo00279a036

文献信息

• Benzaldehyde oxime as a 1,3-dipole chameleon
  作者：Albert Padwa、William Dent、Philip E. Yeske

  DOI：10.1021/jo00226a050

  日期：1987.8
• New synthesis of .beta.-lactams based on nitrone cycloaddition to nitroalkenes
  作者：Albert Padwa、Konrad F. Koehler、Augusto Rodriguez

  DOI：10.1021/jo00176a013

  日期：1984.1
• Thiones as Superdipolarophiles. Rates and Equilibria of Nitrone Cycloadditions to Thioketones
  作者：Rolf Huisgen、Lubor Fisera、Henry Giera、Reiner Sustmann

  DOI：10.1021/ja00143a008

  日期：1995.9

  1,3-Dipolar cycloadditions of N-methyl-C,C-diphenylnitrone (15) and N-methyl-C-phenylnitrone (16) with aliphatic thioketones are equilibrium reactions. The 1,4,2-oxathiazolidines were characterized and their dissociation constants measured by H-1 NMR analysis and by visible spectrophotometry. K-diss Of the adduct 28 from 16 and 2,2,6,6-tetramethylcyclohexanethione (27) was determined from 20-76 degrees C, revealing Delta H-add = -10.8 kcal mol(-1) and Delta S-add = -28 eu. The inertness of diaryl thioketones vs nitrones has thermodynamic reasons. According to rate measurements with 16, the activity of the highly hindered thione 27 exceeds 5-fold that of dimethyl acetylenedicarboxylate (DMAD), the top dipolarophile with a CC multiple bond; the cycloaddition to adamantanethione-despite adverse steric effects-is 1500 times faster than that to DMAD. Rate constants for the cycloaddition of 16 to 2,2,4,4-tetramethyl-3-thioxocyclobutanone (10) were measured in 12 solvents. The small and slightly inverse relation to solvent polarity rules out a zwitterionic intermediate but is consistent with a concerted pathway.
• PADWA, ALBERT;DENT, WILLIAM H.;SCHOFFSTALL, ALLEN M.;YESKE, PHILIP E., J. ORG. CHEM., 54,(1989) N8, C. 4430-4437
  作者：PADWA, ALBERT、DENT, WILLIAM H.、SCHOFFSTALL, ALLEN M.、YESKE, PHILIP E.

  DOI：——

  日期：——
• PADWA, ALBERT;CHIACCHIO, UGO;KLINE, DONALD N.;PERUMATTAM, JOHN, J. ORG. CHEM., 53,(1988) N 10, 2238-2245
  作者：PADWA, ALBERT、CHIACCHIO, UGO、KLINE, DONALD N.、PERUMATTAM, JOHN

  DOI：——

  日期：——