methyl 2,2,6-trimethyl-2H-pyran-5-carboxylate | 70569-78-7

• 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 2,2,6-trimethyl-2H-pyran-5-carboxylate
• 英文别名: 2,6,6-Trimethyl-6h-pyran-3-carboxylic acid methyl ester；methyl 2,6,6-trimethylpyran-3-carboxylate
• CAS: 70569-78-7
• 化学式: C₁₀H₁₄O₃
• 分子量: 182.219
• InChiKey: BDOVYIWZKIPMKY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  13
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.5
• 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 2,2,6-trimethyl-2H-pyran-5-carboxylate 、 Arsonium, (4-methoxy-2,4-dioxobutyl)triphenyl-, bromide 在 potassium tert-butylate 作用下， 以 四氢呋喃 为溶剂， 以52%的产率得到(1S,2R)-4-Methyl-2-(2-methyl-propenyl)-6-oxo-cyclohex-4-ene-1,3-dicarboxylic acid dimethyl ester
  参考文献：
  名称：

  Novel Michael-Wittig reactions of methyl 3-oxo-4-(triphenylarsoranylidene)butanoate and substituted 2H-pyran-5-carboxylates; The synthesis of highly functionalised 2-cyclohexenonedicarboxylates

  摘要：

  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.

  DOI：

  10.1016/s0040-4020(96)01126-x
• 作为产物：
  描述：

  3-甲基-2-丁烯醛 、 乙酰乙酸甲酯 在 sodium benzoate 、 苄基三乙基氯化铵 作用下， 以 甲醇 为溶剂， 反应 18.0h， 生成 methyl (2Z)-2-acetyl-5-methylhexa-2,4-dienoate 、 methyl 2,2,6-trimethyl-2H-pyran-5-carboxylate
  参考文献：
  名称：

  Synthesis of Substituted Alkyl 2H-Pyran-5-carboxylates

  摘要：

  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。

  DOI：

  10.1055/s-1997-1400

文献信息

• 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。
• Moorhoff, Cornelis M., Journal of Chemical Research, Miniprint, 1997, # 4, p. 866 - 879
  作者：Moorhoff, Cornelis M.

  DOI：——

  日期：——
• KRASNAYA ZH. A.; PROKOFEV E. P.; KUCHEROV V. F., IZV. AN CCCP. CEP. XIM., 1979, HO 4, 816-822
  作者：KRASNAYA ZH. A.、 PROKOFEV E. P.、 KUCHEROV V. F.

  DOI：——

  日期：——
• 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
• 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。