methyl 4-methyl-3,6-dihydro-2H-pyran-2-carboxylate | 38426-34-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡喃
• 英文名称: methyl 4-methyl-3,6-dihydro-2H-pyran-2-carboxylate
• CAS: 38426-34-5
• 化学式: C₈H₁₂O₃
• 分子量: 156.181
• InChiKey: QRVWCQUZQVIMFD-UHFFFAOYSA-N

物化性质

• 沸点：
  199.1±40.0 °C(Predicted)
• 密度：
  1.066±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.6
• 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

• 作为反应物：
  描述：

  methyl 4-methyl-3,6-dihydro-2H-pyran-2-carboxylate 在 platinum on activated charcoal lithium aluminium tetrahydride 、 氢气 作用下， 以 甲醇 、 乙醚 为溶剂， 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：

  5-Hexenoic acid, 2-hydroxy-4-methylene-, butyl ester 在 硫酸 作用下， 以 甲醇 、 乙醚 为溶剂， 反应 3.0h， 生成 methyl 4-methyl-3,6-dihydro-2H-pyran-2-carboxylate
  参考文献：
  名称：

  Aqueous hetero Diels-Alder reactions: The carbonyl case.

  摘要：

  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.

  DOI：

  10.1016/s0040-4020(01)81759-2

文献信息

• Merging Photoredox and Nickel Catalysis: Decarboxylative Cross-Coupling of Carboxylic Acids with Vinyl Halides
  作者：Adam Noble、Stefan J. McCarver、David W. C. MacMillan

  DOI：10.1021/ja511913h

  日期：2015.1.21

  Decarboxylative cross-coupling of alkyl carboxylic acids with vinyl halides has been accomplished through the synergistic merger of photoredox and nickel catalysis. This new methodology has been successfully applied to a variety of α-oxy and α-amino acids, as well as simple hydrocarbon-substituted acids. Diverse vinyl iodides and bromides give rise to vinylation products in high efficiency under mild

  烷基羧酸与乙烯基卤化物的脱羧交叉偶联是通过光氧化还原和镍催化的协同合并实现的。这种新方法已成功应用于各种α-氧基和α-氨基酸，以及简单的烃取代酸。不同的乙烯基碘化物和溴化物在温和、操作简单的反应条件下高效地产生乙烯基化产物。
• 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.
• 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.