butyl 4-methyl-3,6-dihydro-2H-pyran-2-carboxylate | 27944-72-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡喃
• 英文名称: butyl 4-methyl-3,6-dihydro-2H-pyran-2-carboxylate
• CAS: 27944-72-5
• 化学式: C₁₁H₁₈O₃
• 分子量: 198.262
• InChiKey: MTBIWOKGXWVPIE-UHFFFAOYSA-N

物化性质

• 沸点：
  257.7±40.0 °C(Predicted)
• 密度：
  1.012±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  14
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.73
• 拓扑面积：
  35.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  butyl 4-methyl-3,6-dihydro-2H-pyran-2-carboxylate 在 platinum on activated charcoal lithium aluminium tetrahydride 、 硫酸 、 氢气 作用下， 以 甲醇 、 乙醚 为溶剂， 反应 4.0h， 生成 trans-2-hydroxymethyl-4-methyltetrahydropyran
  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
• 作为产物：
  描述：

  乙醛酸正丁酯 、 天然橡胶 在 对苯二酚 作用下， 反应 8.0h， 生成 butyl 4-methyl-3,6-dihydro-2H-pyran-2-carboxylate
  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

• Glyoxylate-Ene Reaction Catalyzed by Ln(OTf)3
  作者：Changtao Qian、Taisheng Huang

  DOI：10.1016/s0040-4039(97)01536-0

  日期：1997.9

  Yb(OTf)(3), can catalyze the glyoxylate-ene reaction effectively as a water-stable and reusable catalyst. Moreover, the selectivity of DA product or ene product can be adjusted by solvents in the reaction of glyoxylates with a diene (isoprene). In the presence of chiral ytterbium complexes generated in situ from Yb(OTf)(3) and optical 6,6'-disubstituted binaphthols, methyl glyoxylate smoothly reacts with alpha-methyl styrene to afford alpha-hydroxyl esters in modest optical yields. (C) 1997 Elsevier Science Ltd.
• 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.