diethyl 6-methyl-2-oxo-2H-pyran-4,5-dicarboxylate

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡喃
• 英文名称: diethyl 6-methyl-2-oxo-2H-pyran-4,5-dicarboxylate
• 英文别名: 4,5-bis(ethoxycarbonyl)-6-methyl-2H-pyran-2-one；Diethyl 2-methyl-6-oxopyran-3,4-dicarboxylate；diethyl 2-methyl-6-oxopyran-3,4-dicarboxylate
• 化学式: C₁₂H₁₄O₆
• 分子量: 254.24
• InChiKey: MGSGRQMXGSYYEP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1
• 重原子数：
  18
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  78.9
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  乙酰乙酸乙酯 、 丁炔二酸二乙酯 在 三乙烯二胺 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 1.0h， 以86%的产率得到diethyl 6-methyl-2-oxo-2H-pyran-4,5-dicarboxylate
  参考文献：
  名称：

  DABCO催化缺电子炔烃与1,3-二羰基化合物之间的C–C键形成反应

  摘要：

  已发现出色的催化剂DABCO可以催化活化的亚甲基与炔烃之间的C–C键形成反应。该转化为2 H-吡喃-2-酮或不饱和链烯酸酯衍生物的合成提供了一条简便的途径，并探索了N-催化剂用于将炔烃与链烷酸酯迈克尔加成的新可能性。

  DOI：

  10.1016/j.tet.2012.03.047

文献信息

• DABCO-catalyzed C–C bond formation reaction between electron-deficient alkynes and 1,3-dicarbonyl compounds
  作者：Hua Cao、Haiping Zhong、Yuanguang Lin、Liuqing Yang

  DOI：10.1016/j.tet.2012.03.047

  日期：2012.5

  excellent catalyst DABCO has been found to catalyze C–C bond formation reaction between activated methylenes and alkynes. The transformation has provided a facile route for the synthesis of 2H-pyran-2-ones or unsaturated alkenoic acid ester derivatives and explored the new possibilities of N-catalysts for Michael addition of nucleophiles with alkynoates.

  已发现出色的催化剂DABCO可以催化活化的亚甲基与炔烃之间的C–C键形成反应。该转化为2 H-吡喃-2-酮或不饱和链烯酸酯衍生物的合成提供了一条简便的途径，并探索了N-催化剂用于将炔烃与链烷酸酯迈克尔加成的新可能性。
• Hydroalkylation leading to heterocyclic compounds. Part 1: New strategies for the synthesis of polysubstituted 2H-pyran-2-ones
  作者：Wei-Bing Liu、Huan-Feng Jiang、Chun-Li Qiao

  DOI：10.1016/j.tet.2008.12.069

  日期：2009.3

  Polysubstituted 2H-pyran-2-ones and 5,6-dihydro-2H-pyran-2-ones were synthesized via the MCRs initiated by the hydroalkylation of alkynoates with activated methylenes. Under the optimized reaction conditions, the desired products were obtained in 47–88% isolated yields. The experimental results showed that the groups on activated methylenes act important roles in the nucleophilic attack fashion.

  经由MCR合成多取代的2 H-吡喃-2-酮和5,6-二氢-2 H-吡喃-2-酮，所述MCR是通过炔烃与活化的亚甲基的加氢烷基化反应而引发的。在优化的反应条件下，所需产物的分离产率为47-88％。实验结果表明，活化亚甲基上的基团以亲核攻击方式起着重要作用。
• Synthesis of Polysubstituted α-Pyrones Using Zinc-Catalyzed Addition-Cyclization Reactions
  作者：Wei-Bing Liu、Cui Chen、Qing Zhang、Zhi-Bo Zhu

  DOI：10.1002/jhet.1698

  日期：2014.9

  Various polysubstituted α‐pyrone derivatives have been directly synthesized via a hydroalkylation of Michael additional reaction following a cyclized process catalyzed by the Lewis acid of Zn(OAc)2. This protocol provides a new convenient and step‐economical route to construct heterocycles. Fourteen examples are obtained from easily available materials with moderate to good yields.

  在Zn（OAc）2的路易斯酸催化的环化过程之后，通过迈克尔附加反应的加氢烷基化反应已直接合成了各种多取代的α-吡喃酮衍生物。该协议为构建杂环化合物提供了一种新的便捷且经济的途径。从容易获得的材料中获得了十四个示例，它们具有中等到良好的产率。
• ReBr(CO)5-catalyzed sequential addition–cyclization of 1,3-dicarbonyl compounds with electron-deficient internal alkynes affording trisubstituted 2H-pyran-2-ones
  作者：Wen-Guo Zhao、Ruimao Hua

  DOI：10.1016/j.tet.2007.09.038

  日期：2007.11

  The reaction of 1,3-dicarbonyl compounds such as acetoacetate, acetylacetone, dibenzoylmethane, and benzoylacetate with electron-deficient internal alkynes in the presence of catalytic amount of ReBr( CO) 5 in toluene under neutral conditions resulted in the formation of 4,5,6-trisubstituted 2H-pyran-2-ones in moderate to high yield. The reaction took place via a two-step sequence including the rhenium(I)-catalyzed addition of the activated methylenes to alkynes to give enolic 2-alkenyl derivatives, and subsequently dealcoholic cyclization to form 2H-pyran-2-one derivatives. (c) 2007 Elsevier Ltd. All rights reserved.
• Copper oxide catalyzed domino process for the synthesis of substituted 2H-pyran-2-ones and polyhydroxy coumarin derivatives
  作者：Utpal Kayal、Rajiv Karmakar、Dipanwita Banerjee、Gourhari Maiti

  DOI：10.1016/j.tet.2014.07.032

  日期：2014.9