cis-2-carbomethoxy-4,6-dimethyl-3,6-dihydro-2H-pyran

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡喃
• 英文名称: cis-2-carbomethoxy-4,6-dimethyl-3,6-dihydro-2H-pyran
• 英文别名: methyl (2S,6S)-4,6-dimethyl-3,6-dihydro-2H-pyran-2-carboxylate
• 化学式: C₉H₁₄O₃
• 分子量: 170.208
• InChiKey: KETDYUVKNKVALP-YUMQZZPRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1
• 重原子数：
  12
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  35.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  2-甲基-1,3-戊二烯 在 硫酸 、 对苯二酚 作用下， 反应 12.0h， 生成 cis-2-carbomethoxy-4,6-dimethyl-3,6-dihydro-2H-pyran
  参考文献：
  名称：

  Carbon-13 NMR spectra of saturated heterocycles: XI—Tetrahydropyrans (oxanes)

  摘要：

  AbstractThe 13C NMR spectra of 62 oxanes (tetrahydropyrans) with and without methyl substituents at various ring positions, some of them bearing in addition (or instead) ethyl, vinyl, ethynyl, carbomethoxy and methylol substituents at C‐2, have been recorded, and the 294 resulting chemical shifts have been correlated by multiple linear regression analysis. Axial and equatorial α‐, β‐, γ‐, δ‐, gem‐ and vic‐parameters for shifts caused by methyl groups at all ring positions, and similar parameters for Et,—CHCH2,—CCH, CO2Me and CH2OH groups at C‐2, are reported. Standard deviations of the parameters are, in most cases, within 0.3 ppm and the agreement of calculated and experimental shifts is excellent. This is probably the largest parameter set of this type extant. 13C NMR spectra of a number of additional substituted tetrahydropyrans, and of 3,6‐dihydro‐2H‐pyrans and 3,4‐dihydro‐2H‐pyrans, are tabulated and discussed.

  DOI：

  10.1002/omr.1270210205

文献信息

• Reactions de cycloaddition [4 + 2] sous micro - ondes des derives du glyoxal
  作者：A. Stambouli、M. Chastrette、M. Soufiaoui

  DOI：10.1016/s0040-4039(00)74313-9

  日期：1991.4

  Hetero Diels-Alder reactions of methylglyoxylate and glyoxal monoacetal with 2-methyl-1,3-pentadiene have been studied under pressure in a microwave oven. Reaction times were dramatically reduced and degradation and polymerisation were avoided.
• Aqueous hetero Diels-Alder reactions: The carbonyl case.
  作者：A. Lubineau、J. Augé、E. Grand、N. Lubin

  DOI：10.1016/s0040-4020(01)81759-2

  日期：1994.8

  Commercially available aqueous solution of glyoxylic acid, pyruvaldehyde and glyoxal were shown to react with cyclic or non-cyclic dienes to give the corresponding cycloadducts and/or alpha-hydroxy gamma-lactones. Activated ketone (Pyruvic acid) was shown to react as well in the same conditions.
• Carbon-13 NMR spectra of saturated heterocycles: XI—Tetrahydropyrans (oxanes)
  作者：Ernest L. Eliel、Muthiah Manoharan、K. Michal Pietrusiewicz、Karl D. Hargrave

  DOI：10.1002/omr.1270210205

  日期：1983.2

  AbstractThe 13C NMR spectra of 62 oxanes (tetrahydropyrans) with and without methyl substituents at various ring positions, some of them bearing in addition (or instead) ethyl, vinyl, ethynyl, carbomethoxy and methylol substituents at C‐2, have been recorded, and the 294 resulting chemical shifts have been correlated by multiple linear regression analysis. Axial and equatorial α‐, β‐, γ‐, δ‐, gem‐ and vic‐parameters for shifts caused by methyl groups at all ring positions, and similar parameters for Et,—CHCH2,—CCH, CO2Me and CH2OH groups at C‐2, are reported. Standard deviations of the parameters are, in most cases, within 0.3 ppm and the agreement of calculated and experimental shifts is excellent. This is probably the largest parameter set of this type extant. 13C NMR spectra of a number of additional substituted tetrahydropyrans, and of 3,6‐dihydro‐2H‐pyrans and 3,4‐dihydro‐2H‐pyrans, are tabulated and discussed.