4-carbomethoxy-N-methyl-3-phenylisoxazoline | 87352-10-1

• 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-phenylisoxazoline
• 英文别名: 2-methyl-3-phenyl-5-carbomethoxy-4-isoxazoline；N-methyl-5-carbomethoxy-3-phenyl-4,5-dehydroisoxazolidine；2-Methyl-3-phenyl-Δ⁴-isoxazolin-5-carbonsaeure-methylester；2-methyl-3-phenyl-2,3-dihydro-isoxazole-5-carboxylic acid methyl ester；5-Isoxazolecarboxylic acid, 2,3-dihydro-2-methyl-3-phenyl-, methyl ester；methyl 2-methyl-3-phenyl-3H-1,2-oxazole-5-carboxylate
• CAS: 87352-10-1
• 化学式: C₁₂H₁₃NO₃
• 分子量: 219.24
• InChiKey: VQQMAAFLAKVQBM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 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-phenylisoxazoline 在 间氯过氧苯甲酸 作用下， 以 二氯甲烷 为溶剂， 反应 4.0h， 以98%的产率得到2-氧代-4-苯基-3-丁酸甲酯
  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：

  trans-N-Methyl-5-carbomethoxy-4-nitro-trans-3-phenylisoxazolidine 在 potassium tert-butylate 作用下， 以 二甲基亚砜 为溶剂， 反应 6.0h， 以70%的产率得到4-carbomethoxy-N-methyl-3-phenylisoxazoline
  参考文献：
  名称：

  New synthesis of .beta.-lactams based on nitrone cycloaddition to nitroalkenes

  摘要：

  DOI：

  10.1021/jo00176a013

文献信息

• Silyl group transfer in the cycloaddition reactions of silyl iminium salts derived from aryl-substituted oximes
  作者：Albert Padwa、William H. Dent、Allen M. Schoffstall、Philip E. Yeske

  DOI：10.1021/jo00279a036

  日期：1989.9
• 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
• 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：——