ethyl 5,6,7,8-tetrahydro-7,7-dimethyl-2,5-dioxo-2H-1-benzopyran-4-carboxylate | 33886-29-2

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: ethyl 5,6,7,8-tetrahydro-7,7-dimethyl-2,5-dioxo-2H-1-benzopyran-4-carboxylate
• 英文别名: ethyl 5,6,7,8-tetrahydro-7,7-dimethyl-2,5-dioxo-2H-chromene-4-carboxylate；ethyl 7,7-dimethyl-2,5-dioxo-5,6,7,8-tetrahydro-2H-chromene-4-carboxylate；7,7-dimethyl-2,5-dioxo-5,6,7,8-tetrahydro-2H-chromene-4-carboxylic acid ethyl ester；Ethyl 7,7-dimethyl-2,5-dioxo-6,8-dihydrochromene-4-carboxylate；ethyl 7,7-dimethyl-2,5-dioxo-6,8-dihydrochromene-4-carboxylate
• CAS: 33886-29-2
• 化学式: C₁₄H₁₆O₅
• 分子量: 264.278
• InChiKey: LXDJDSVPGSWZEJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  19
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  69.7
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  在 silica gel 作用下， 反应 0.15h， 生成 ethyl 5,6,7,8-tetrahydro-7,7-dimethyl-2,5-dioxo-2H-1-benzopyran-4-carboxylate
  参考文献：
  名称：

  在无溶剂条件下，在硅胶粉末存在的情况下，稳定的磷叶立德通过微波诱导转化为缺电子的 2H-Cheromenes

  摘要：

  在三苯基膦和二烷基乙炔二羧酸酯之间的反应中产生的高反应性 1:1 中间体被环己 1,3-二酮质子化产生乙烯基三苯基鏻盐，其与共轭碱发生迈克尔加成反应以产生稳定的磷叶立德。发现硅胶粉末在无溶剂条件下，在微波辐射（0.72 KW，9 分钟）或热条件（95°C，45 分钟）下催化稳定的磷叶立德转化为相应的缺电子 2H-色烯。相当不错的收益。

  DOI：

  10.1080/10426500600864395

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。
• One-Pot Synthesis of Functionalized 2H-Chromene (=2H-1-Benzopyran) Derivatives via a Three-Component Reaction between a CH-Acid, a Dialkyl Acetylenedicarboxylate, and Methyl Chloroglyoxylate or Benzyl Carbonochloridate Mediated by Triphenylphosphine
  作者：Mohammad Bayat、Nader Zabarjad Shiraz、Soheila Shafei Asayesh

  DOI：10.1002/hlca.201000030

  日期：2010.11

  An effective route to functionalized 2H‐chromene (=2H‐1‐benzopyran) derivatives 4 is described (Scheme 1). This involves the reaction of a 1,1‐diactivated alkene, resulting from the reaction of dimedone (=5,5‐dimethylcyclohexane‐1,3‐dione; 1a) with methyl chloroglyoxylate (ClC(O)COOMe), benzyl carbonochloridate (ClC(O)OCH2Ph) or 3,5‐dinitrobenzoyl chloride (3,5‐(NO2)2C6H3C(O)Cl), and a dialkyl

  描述了一种功能化的2 H-色烯（= 2 H -1-苯并吡喃）衍生物4的有效途径（方案1）。这涉及1,1-双活化烯烃的反应，这是由二甲酮（= 5,5-二甲基环己烷-1,3-二酮; 1a）与氯乙醛酸甲酯（ClC（= O）COOMe），苄基氯代氯酸（ ClC（O）OCH 2 Ph）或3,5-二硝基苯甲酰氯（3,5-（NO 2）2 C 6 H 3 C（O）Cl）和乙炔基二羧酸二烷基酯（=二烷基丁-2-炔二酸酯） ）在存在分子内Wittig反应以生成2的Ph 3 P存在下H-色烯衍生物（方案1）。
• 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
• Isoquinoline-catalyzed reaction between 4-hydroxycoumarin or 4-hydroxy-6-methylpyran-1-one and dialkyl acetylene dicarboxylates: synthesis of coumarin and pyranopyrane derivatives
  作者：Mohammad Anary-Abbasinejad、Hossein Anaraki-Ardakani、Mohammad Hossein Mosslemin、Hamid Reza Khavasi

  DOI：10.1590/s0103-50532010000200018

  日期：——

  In this work we report the reaction between dialkyl acetylenedicarboxylates and enolic systems such as 5,5-dimethyl-1,3-cyclohexanedione, 1,3-cyclohexanedione, 4-hydroxycoumarin or 4-hydroxy-6-methylpyran-1-one in the presence of isoquinoline, which leads to new coumarin and pyranopyran derivatives.
• Reaction between dialkyl acetylenedicarboxylates and six-membered 1,3-diketones in the presence of trialkylamines: a convenient synthesis of alkyl 2,5-dioxo-5,6,7,8-tetrahydro-2H-chromene-4-carboxylates
  作者：Farough Nasiri、Kourosh Pourdavaie、Samiyeh Yosefdad、Bahareh Atashkar

  DOI：10.1016/j.mencom.2007.11.019

  日期：2007.11

  The reaction of dialkyl acetylenedicarboxylates with six-membered cyclic 1,3-diketones such as 1,3-cyclohexanedione or 5,5-dimethyl-1,3-cyclohexanedione in the presence of a catalytic amount of trimethylamine, triethylamine or tributylamine in CH(2)Cl(2) leads to alkyl 2,5-dioxo-5,6,7,8-tetrahydro-2H-chromene-4-carboxylates in good yields.