4-甲氧基-6-甲基-5,6-二氢吡喃-2-酮 | 3791-79-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡喃
• 中文名称: 4-甲氧基-6-甲基-5,6-二氢吡喃-2-酮
• 英文名称: 4-methoxy-6-methyl-5,6-dihydro-2-pyrone
• 英文别名: 4-methoxy-6-methyl-5,6-dihydro-2H-pyran-2-one；4-methoxy-2-methyl-2,3-dihydropyran-6-one
• CAS: 3791-79-5
• 化学式: C₇H₁₀O₃
• 分子量: 142.155
• InChiKey: TWJYJKOEWGZNIB-UHFFFAOYSA-N

物化性质

• 熔点：
  69 °C
• 沸点：
  289.2±40.0 °C(Predicted)
• 密度：
  1.09±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.8
• 重原子数：
  10
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.57
• 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：

  4-甲氧基-6-甲基-5,6-二氢吡喃-2-酮 在 N-氯代丁二酰亚胺 作用下， 以 四氯化碳 为溶剂， 反应 1.0h， 以73%的产率得到3-Chloro-4-methoxy-6-methyl-5,6-dihydro-2-pyranone
  参考文献：
  名称：

  Lokot; Pashkovskii; Lakhvich, Russian Journal of Organic Chemistry, 1998, vol. 34, # 9, p. 1350 - 1354

  摘要：

  DOI：
• 作为产物：
  描述：

  4-甲氧基-6-甲基-2H-吡喃酮 在 5% Pd/Al2O3 、 氢气 作用下， 以 异丙醇 为溶剂， 20.0 ℃ 、200.0 kPa 条件下， 生成 4-甲氧基-6-甲基-5,6-二氢吡喃-2-酮
  参考文献：
  名称：

  Fundamental insights into the enantioselectivity of hydrogenations on cinchona-modified platinum and palladium

  摘要：

  The influence of the configuration at the C8 and C9 positions of cinchona alkaloids was investigated by comparing the efficiency of cinchonidine, cinchonine, and 9-epi-cinchonidine as chiral modifiers. In the hydrogenation of ketones (methyl benzoylformate, ketopantolactone, methylglyoxal dimethylacetal, 2,2,2-trifluoroacetophenone) on Pt, a change in the configuration at C9 did not affect the absolute configuration of the main products; however, the ees and rates dropped significantly. In the hydrogenation of alpha-functionalized olefins (E-2-methyl-2-hexenoic acid, 2-phenylcinnamic acid, and 4-methoxy-6-methyl-2H-pyran-2-one) on Pd, replacement of cinchonidine or cinchonine by epi-cinchonidine diminished the rates and almost eliminated the enantioselection, indicating that a subtle combination of C8 and C9 configurations is required on Pd. DFT calculations of the adsorption of the modifiers and the nonlinear behavior of modifier mixtures revealed that the lower reaction rates observed for 9-epi-cinchonidine-modified surfaces cannot be related to different adsorption strength of this modifier. Additionally, substrate-modifier docking interactions are presented. (C) 2012 Elsevier Inc. All rights reserved.

  DOI：

  10.1016/j.jcat.2012.02.018

文献信息

• Hydrogenations of triacetic acid lactone. A new synthesis of the carpenter bee ( ) sex pheromone
  作者：R. Bacardit、M. Moreno-Mañas

  DOI：10.1016/s0040-4039(01)85553-2

  日期：1980.1

  under a variety of catalytic conditions, triacetic acid lactone, I, has been hydrogenated to differently oxidized lactones (II, III and V). C-Methylation of one of them, (II) is the key step for a convenient preparation of the carpenter bee sex pheromone.

  在各种催化条件下，三乙酸内酯（Ⅰ）已被氢化成不同氧化态的内酯（Ⅱ，Ⅲ和Ⅴ）。其中一个（II）的C-甲基化是方便制备木匠蜂性信息素的关键步骤。
• Simple and efficient synthesis of thysanone methyl ether
  作者：Vivek J. Bulbule、Priti S. Koranne、Vishnu H. Deshpande、Hanumant B. Borate

  DOI：10.1016/j.tet.2006.10.038

  日期：2007.1

  The synthesis of thysanone methyl ether is achieved by employing semivioxanthin methyl ether, which in turn is prepared by the tandem Michael addition of an anion of orsellinate to a substituted dihydropyrone.

  胸腺嘧啶甲基醚的合成是通过使用半紫黄质甲基醚来实现的，而半紫黄质甲基醚又是通过将山梨酸根阴离子串联到取代的二氢吡喃酮上而制得的。
• Synthesis, Biosynthesis, and Absolute Configuration of Vioxanthin
  作者：Silke E. Bode、Daniel Drochner、Michael Müller

  DOI：10.1002/anie.200701014

  日期：2007.8.3
• Asymmetric Hydrogenation of Substituted 2-Pyrones
  作者：Matthias J. Fehr、Giambattista Consiglio、Michelangelo Scalone、Rudolf Schmid

  DOI：10.1021/jo982215l

  日期：1999.8.1

  Various substituted 2-pyrones have been hydrogenated with high enantioselectivity (up to 97% ee) to the corresponding 5,6-dihydropyrones using cationic ruthenium catalysts containing the (6,6'-dimethoxybiphenyl-2,2'diyl)bis[3,5-di(tert-butyl)phenylphosphine] ligand. When substituents at position 3 are absent, 5,6-dihydropyrones are further hydrogenated to the fully saturated delta-lactones. In the case of 4,6-dimethyl-2H-pyran-2-one, the diastereoselectivity of the second hydrogenation step was determined by the chirality of the applied catalyst, while for the 4,5,6-trimethyl-2H-pyran-2-one a double asymmetric induction effect was observed. Other cyclic substrates with endo- or exocyclic double bonds were hydrogenated, although with substantially lower enantioselectivity with respect to the 2-pyrones.
• 304. Unsaturated lactones. Part II. (Researches on acetylenic compounds. Part XIX.) Reactions of the esters of αβ-acetylenic hydroxy-acids with nucleophilic reagents
  作者：E. R. H. Jones、M. C. Whiting

  DOI：10.1039/jr9490001423

  日期：——