methyl 2,6-dimethyl-2H-pyran-5-carboxylate | 70569-81-2

• 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 2,6-dimethyl-2H-pyran-5-carboxylate
• 英文别名: (r,s)-2,6-Dimethyl-6h-pyran-3-carboxylic acid methyl ester
• CAS: 70569-81-2
• 化学式: C₉H₁₂O₃
• 分子量: 168.192
• InChiKey: GEHNNJBHMGFWPS-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  12
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.44
• 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 3-oxo-4-(triphenylphosphoranylidene)butanoate 、 methyl 2,6-dimethyl-2H-pyran-5-carboxylate 在 对苯二酚 作用下， 以 苯 为溶剂， 反应 4.0h， 以33%的产率得到dimethyl 6-methyl-2-(prop-1-enyl)-4-oxocyclohex-5-ene-1,3-dicarboxylate
  参考文献：
  名称：

  新的环化技术；鏻叶立德和取代的 2H-Pyran-5-carboxylates 的缩合；环己烯酮二羧酸盐和环己二烯二羧酸盐的制备

  摘要：

  取代的 2H-吡喃-5-羧酸烷基酯与 3-氧代-4-(三苯基正膦亚基)丁酸烷基酯和 4-(三苯基正膦亚基)-2-丁烯酸烷基酯缩合形成取代的 2-乙烯基-6-氧代-4-环己烯- 1,3-二羧酸盐，其中一些在宠物和牛中显示出体外杀寄生虫活性，并分别取代了 2-vinyl-3,5-cyclohexadiene-1,3-dicarboxylates。最后提到的产品与使用相应的砷类似物获得的产品形成鲜明对比。

  DOI：

  10.1002/jccs.200300064
• 作为产物：
  描述：

  乙酰乙酸甲酯 、 巴豆醛 、 哌啶 以38%的产率得到
  参考文献：
  名称：

  KRASNAYA ZH. A.; PROKOFEV E. P.; KUCHEROV V. F., IZV. AN CCCP. CEP. XIM., 1979, HO 4, 816-822

  摘要：

  DOI：

文献信息

• Synthesis of Substituted Alkyl 2H-Pyran-5-carboxylates
  作者：Cornelis M. Moorhoff

  DOI：10.1055/s-1997-1400

  日期：1997.6

  The successful synthesis of substituted alkyl 2H-pyran-5-carboxylates 3 from substituted alkyl 3-oxobutanoates 1 and conjugated aldehydes 2 is described.

  成功合成了取代烷基2H-吡喃-5-羧酸酯3，这一过程是通过取代烷基3-氧代丁酸酯1和共轭醛2反应得到的。
• Moorhoff, Cornelis M., Journal of Chemical Research, Miniprint, 1997, # 4, p. 866 - 879
  作者：Moorhoff, Cornelis M.

  DOI：——

  日期：——
• Novel Michael-Wittig reactions of methyl 3-oxo-4-(triphenylarsoranylidene)butanoate and substituted 2H-pyran-5-carboxylates; The synthesis of highly functionalised 2-cyclohexenonedicarboxylates
  作者：Cornelis M. Moorhoff

  DOI：10.1016/s0040-4020(96)01126-x

  日期：1997.2

  Novel Michael-Wittig condensations of methyl 3-oxo-4-(triphenylarsoranylidene)-butanoate 6 and substituted 2,2-dimethyl-2H-pyran-5-carboxylates 5a to 5e gave substituted 4-alkyl-6-oxo-4-cyclohexene-1,3-dicarboxylates 8a to 8e in a mixture of three keto diastereomers and two enol diastereomers. Apart from substituted 4-alkyl-6-oxo-4-cyclohexene-1,3-dicarboxylates 8f to 8g, less hindered substituted 2-methyl-2H-pyran-5-carboxylates 5f and 5g gave the substituted tetrahydrobenzofurans 9f and 9g. 4-Halomethyl-6-oxo-4-cyclohexene 1,1-dicarboxylates 8 were mostly in the enol diastereomeric form. A plausible mechanism is given for the unique formation for these products. (C) 1997, Elsevier Science Ltd.
• Novel reactions of arsonium ylides and substituted 2H-pyran-5-carboxylates, a new preparation for functionalised vinylcyclopropanecarboxylates and dihydrofurans
  作者：Cornelis M Moorhoff

  DOI：10.1016/s0040-4039(97)82961-9

  日期：1996.12

  Substituted alkyl 2-pyran-5-carboxylates have been condensed with arsonium ylides to farm substituted vinylcyclopropanecarboxylates and in a number of cases also vinyldihydrofurans. Copyright (C) 1996 Published by Elsevier Science Ltd
• New Annulation Techniques; Condensations of Phosphonium Ylides and Substituted 2<i>H</i>-Pyran-5-carboxylates; Preparation of Cyclohexenonedicarboxylates and Cyclohexadienedicarboxylates
  作者：Cornelis M. Moorhoff

  DOI：10.1002/jccs.200300064

  日期：2003.6

  Substituted alkyl 2H-pyran-5-carboxylates condensed with alkyl 3-oxo-4-(triphenylphosphoranyl-idene)butanoate and alkyl 4-(triphenylphosphoranylidene)-2-butenoate to form substituted 2-vinyl-6-oxo-4-cyclohexene-1,3-dicarboxylates, some of which showed ecto-parasiticidal activity in pets and cattle, and substituted 2-vinyl-3,5-cyclohexadiene-1,3-dicarboxylates, respectively. The last mentioned product

  取代的 2H-吡喃-5-羧酸烷基酯与 3-氧代-4-(三苯基正膦亚基)丁酸烷基酯和 4-(三苯基正膦亚基)-2-丁烯酸烷基酯缩合形成取代的 2-乙烯基-6-氧代-4-环己烯- 1,3-二羧酸盐，其中一些在宠物和牛中显示出体外杀寄生虫活性，并分别取代了 2-vinyl-3,5-cyclohexadiene-1,3-dicarboxylates。最后提到的产品与使用相应的砷类似物获得的产品形成鲜明对比。