trans-2-carbomethoxy-6-methyl-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: trans-2-carbomethoxy-6-methyl-3,6-dihydro-2H-pyran
• 英文别名: methyl (2S,6R)-6-methyl-3,6-dihydro-2H-pyran-2-carboxylate
• 化学式: C₈H₁₂O₃
• 分子量: 156.181
• InChiKey: IESTWZYTOYHTJO-RQJHMYQMSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.1
• 重原子数：
  11
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.62
• 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：

  间戊二烯 、 alkaline earth salt of/the/ methylsulfuric acid 在 硫酸 、 对苯二酚 作用下， 反应 12.0h， 生成 trans-2-carbomethoxy-6-methyl-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

• Reverse anomeric effect of the carbamoyl group of 2,6-disubstituted 6-carbamoyl-5,6-dihydro-2H-pyrans
  作者：Marek Chmielewski、Janusz Jurczak、Waldemar Priebe、Derek Horton

  DOI：10.1002/mrc.1260250215

  日期：1987.2

  2,6‐disubstituted 6‐carbamoyl‐5,6‐dihydro‐2H‐pyrans and their 6‐methoxycarbonyl analogs have been recorded. With the use of coupling constants between ring protons, the conformational preference of the carbamoyl group has been evaluated. The 1H6⇌6H1 conformational equilibria in the above compounds are discussed. It is found that the conformational tendency of the carbamoyl group to the equatorial disposition

  已记录了 2,6-二取代的 6-氨基甲酰基-5,6-二氢-2H-吡喃及其 6-甲氧基羰基类似物的 1H NMR 光谱。通过使用环质子之间的耦合常数，已经评估了氨基甲酰基的构象偏好。讨论了上述化合物中的 1H6⇌6H1 构象平衡。发现氨基甲酰基的赤道配置的构象趋势有助于确定所研究的七个实施例中的构象平衡。
• 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.