2-methoxy-5-methyl-3,4-dihydro-2H-pyran | 38328-65-3

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2-methoxy-5-methyl-3,4-dihydro-2H-pyran
• 英文别名: 2-methoxy-5-methyl-3,4-dihydro-2H-pyran
• CAS: 38328-65-3
• 化学式: C₇H₁₂O₂
• 分子量: 128.171
• InChiKey: JUUFWWRVYFXMAH-UHFFFAOYSA-N

物化性质

• 沸点：
  167.4±39.0 °C(Predicted)
• 密度：
  0.97±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.1
• 重原子数：
  9
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.71
• 拓扑面积：
  18.5
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  2-methoxy-5-methyl-3,4-dihydro-2H-pyran 在 palladium on activated charcoal 氢气 、 对甲苯磺酸 作用下， 以 甲醇 为溶剂， 25.0 ℃ 、275.79 kPa 条件下， 反应 26.0h， 生成 (2S,5R)-2-Methoxy-5-methyl-tetrahydro-pyran
  参考文献：
  名称：

  Anomeric effect enhancement in C-5-substituted 2-methoxytetrahydropyrans

  摘要：

  cis- and trans-2,5-Dimethoxytetrahydropyrans, cis-2,5-dimethoxy-6-methyltetrahydropyran and 2-methoxy-5-methyltetrahydropyran have been examined to see the effect of an OCH3 group at position 5 on the degree of anomeric effect in substituted 2-methoxytetrahydropyrans. The present study shows that this group stabilises the C-2 electronegative substituent in the axial position. Semi-empirical and ab initio molecular orbital calculations support this view. AM1 calculation gives lower enthalpies as well as lower dipole moments for the compounds having an OCH3 group in the axial position at C-2 over the equatorial form in 2-methoxytetrahydropyrans. This enhanced stabilisation is attributed to the electrostatic interaction between the partial positive charge at C-5 and the partial negative charge of the aglycone oxygen atom. (C) 1997 Elsevier Science B.V.

  DOI：

  10.1016/s0022-2860(97)00001-x
• 作为产物：
  描述：

  乙烯基甲醚 、 2-甲基丙烯醛 在 对苯二酚 作用下， 生成 2-methoxy-5-methyl-3,4-dihydro-2H-pyran
  参考文献：
  名称：

  The 1,4-Addition of Vinyl Ethers to α,β-Unsaturated Carbonyl Compounds

  摘要：

  DOI：

  10.1021/ja01163a076

文献信息

• Production Process Of Tetrahydropyran Compound And Tetrahydropyran Compound Produced By The Production Process
  申请人：Yamagami Isao

  公开号：US20080139828A1

  公开（公告）日：2008-06-12

  The invention provides a production, process of a tetrahydropyran compound, characterized by allowing 3,4-dihydro-2-alkoxy-2H-pyran compound or tetrahydro-2-alkoxy-2H-pyran compound which can be easily prepared through reaction between acrolein and alkylvinylether, with hydrogen in the presence of a catalyst containing an element of Groups VIII to X under acidic condition. The production process of the invention is useful for production of Grignard reaction solvent or polymer solvent and intermediate of organic compound.

  本发明提供了一种四氢吡喃化合物的生产方法，其特点在于在酸性条件下，在含有VIII至X族元素的催化剂存在下，使3,4-二氢-2-烷氧基-2H-吡喃化合物或可以通过丙烯醛和烷基乙烯醚反应轻松制备的四氢-2-烷氧基-2H-吡喃化合物与氢反应。本发明的生产过程适用于格氏试剂反应溶剂或聚合物溶剂和有机化合物的中间体的生产。
• Addition−Rearrangement of Aryl- and Alkoxysulfonyl Isocyanates with 5-Methyl-Substituted 3,4-Dihydro-2-methoxy-<i>2H</i>-pyrans. Selective Synthesis of Functionalized 2-Piperidones¹
  作者：Edwin Jao、Paul B. Slifer、Roger Lalancette、Stan S. Hall

  DOI：10.1021/jo951868o

  日期：1996.1.1

  3,4-Dihydro-2-methoxy-5-methyl-2H-pyran and 3,4-dihydro-2-methoxy-5,6-dimethyl-2H-pyran undergo addition-rearrangement reactions with arylsulfonyl isocyanates to generate the corresponding 3-formyl- and 3-acetyl-6-methoxy-3-methyl-1-(arylsulfonyl)-2-piperidones. For example, 3,4-dihydro-2-methoxy-5-methyl-2H-pyran and phenylsulfonyl isocyanate afforded 3-formyl-6-methoxy-3-methyl-1-(phenylsulfonyl)-2-piperidone as a separable trans/cis mixture in high yield. The more reactive phenoxysulfonyl and alkoxysulfonyl isocyanates provided analogous results.
• Reactions of Acrolein and Related Compounds. I. Addition of Vinyl Ethers
  作者：Curtis W. Smith、Douglas G. Norton、Seaver A. Ballard

  DOI：10.1021/ja01155a076

  日期：1951.11
• Production of glutaraldehyde and csubstituted glutaraldehyde from dihydro pyrans
  申请人：SHELL DEV

  公开号：US02546018A1

  公开（公告）日：1951-03-20
• PRODUCTION PROCESS OF TETRAHYDROPYRAN COMPOUND AND TETRAHYDROPYRAN COMPOUND PRODUCED BY THE PRODUCTION PROCESS
  申请人：SHOWA DENKO KABUSHIKI KAISHA

  公开号：EP1828158A1

  公开（公告）日：2007-09-05