N-[5-(3,4-dimethoxyphenyl)-6-methyl-2-oxo-2H-pyran-3-yl]benzamide | 864777-23-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: N-[5-(3,4-dimethoxyphenyl)-6-methyl-2-oxo-2H-pyran-3-yl]benzamide
• 英文别名: N-[5-(3,4-dimethoxyphenyl)-6-methyl-2-oxopyran-3-yl]benzamide
• CAS: 864777-23-1
• 化学式: C₂₁H₁₉NO₅
• 分子量: 365.386
• InChiKey: CXQMQEHPTWCHEX-UHFFFAOYSA-N

物化性质

• 沸点：
  587.5±50.0 °C(Predicted)
• 密度：
  1.28±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  27
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.14
• 拓扑面积：
  73.9
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  N-[5-(3,4-dimethoxyphenyl)-6-methyl-2-oxo-2H-pyran-3-yl]benzamide 、 3-丁炔-2-酮 以 二氯甲烷 为溶剂， 反应 696.0h， 以97%的产率得到N-(4-acetyl-3',4'-dimethoxy-6-methyl[1,1'-biphenyl]-3-yl)-benzamide
  参考文献：
  名称：

  炔烃高度取代的2 H -pyran-2-ones的Diels-Alder反应：反应性和区域选择性

  摘要：

  提出了多种富电子的2 H-吡喃-2-酮4与炔2的狄尔斯-阿尔德反应在热条件下以及在高压下的反应，生成苯胺衍生物6。根据电子需求以及通过两性离子中间体的形成，定性地解释了在2 H-吡喃-2-酮环上3和5位的取代基对不同炔烃的反应性和区域选择性的影响。

  DOI：

  10.1039/b504852d
• 作为产物：
  描述：

  马尿酸 、 3,4-二甲氧基苯丙酮 、 N,N-二甲基甲酰胺二甲基缩醛 在 乙酸酐 作用下， 反应 8.0h， 以59%的产率得到N-[5-(3,4-dimethoxyphenyl)-6-methyl-2-oxo-2H-pyran-3-yl]benzamide
  参考文献：
  名称：

  3-(苯甲酰氨基)-6-甲基-2-氧代-2H-吡喃-5-羧酸甲酯和N-[5-(3,4-二甲氧基苯基)-6-甲基-2-氧代-2H的合成和晶体结构-吡喃-3-基]苯甲酰胺

  摘要：

  化合物3-(苯甲酰氨基)-6-甲基-2-氧代-2H-吡喃-5-羧酸甲酯(1)、C15H13NO5和N-[5-(3,4-二甲氧基苯基)-6-甲基-2- oxo-2H-pyran-3-yl]benzamide (2), C21H19NO5 结晶为中心对称氢键二聚体，由 N-H...O 相互作用促进，涉及相邻分子内酯基团的酰胺和羰基部分。1 中的超分子聚集受 π-π 相互作用 [质心-质心距离 = 4.0745(11) Å] 和苯甲酰氨基的苯环与羰基原子之间的弱 C-H···O 氢键的组合控制甲氧基羰基和 in 2 通过 π-π 相互作用 [质心-质心距离 = 4.0699(8) 和 4.1556(10) Å]，相邻二甲氧基苯基的甲氧基取代基之间的弱 C-H···O 相互作用和弱 C–H……π 相互作用。

  DOI：

  10.1007/s10870-011-0266-5

文献信息

• Enhancing a Neat Microwave-Assisted Transformation. Diels–Alder Reaction of 2<i>H</i>-Pyran-2-ones toward Fused Bicyclo[2.2.2]octenes
  作者：Krištof Kranjc、Marijan Kocevar

  DOI：10.1246/bcsj.80.2001

  日期：2007.10.15

  An efficient, green access to polysubstituted and highly constrained bicyclo[2.2.2]octenes via a microwave-assisted cycloaddition reaction is described. The double Diels–Alder reaction of a series ...

  描述了通过微波辅助环加成反应获得多取代且高度受限的双环 [2.2.2] 辛烯的高效、绿色途径。一系列的双 Diels-Alder 反应...
• Intensification of a Reaction by the Addition of a Minor Amount of Solvent: Diels-Alder Reaction of 2H-Pyran-2-ones with Alkynes
  作者：Krištof Kranjc、Marijan Kočevar

  DOI：10.1135/cccc20060667

  日期：——

  Diels-Alder transformation of substituted 3-benzoylamino-2H-pyran-2-ones 1 with a variety of alkynes 2 under microwave (MW) irradiation in a closed system can be intensified in a novel way by addition of a minor amount of butan-1-ol. When the reagents are not volatile under the used conditions, the reactions do not seem to be influenced by the addition of butan-1-ol, as demonstrated by the cycloaddition of a fused 2H-pyran-2-one 5 with N-ethylmaleimide (6) giving adduct 7.

  用微波（MW）辐射在封闭系统中对取代的3-苯甲酰氨基-2H-吡喃-2-酮 1 与多种炔烃 2 进行 Diels-Alder 变换，通过添加少量丁醇可以以一种新颖的方式加强反应。当试剂在所用条件下不挥发时，添加丁醇似乎不会影响反应，这由融合的2H-吡喃-2-酮 5 与 N-乙基马来酰亚胺 (6) 发生的环加成反应，生成产物 7 所证明。
• Chloranil as an Efficient Oxidant of the Cyclohexadiene Intermediates Formed by a Cycloaddition of Substituted 2<i>H</i>-Pyran-2-ones and Styrenes En Route to the Boscalid Derivatives
  作者：Jasmin Suljagić、Amadej Juranovič、Marko Krivec、Krištof Kranjc、Marijan Kočevar

  DOI：10.1002/jhet.2603

  日期：2017.1

  between a substituted 2H‐pyran‐2‐one and styrene derivatives, followed by the elimination of CO2 and aromatization (oxidation). The last step was found to be efficiently promoted by the application of chloranil as the oxidant. Alternatively, activated carbon Darco KB could also act as the dehydrogenation catalyst necessitating a larger excess of the styrene to act as the hydrogen acceptor.

  我们描述了一种三步一锅法无金属多米诺法，该方法可产生一组Boscalid衍生物，母体化合物是高度重要的农业化学试剂。该过程的第一步包括取代的2H-吡喃-2-酮与苯乙烯衍生物之间的Diels-Alder反应，然后消除CO 2和芳香化（氧化）。发现通过使用氯腈作为氧化剂可以有效地促进最后一步。或者，活性炭Darco KB也可以用作脱氢催化剂，需要大量过量的苯乙烯作为氢受体。
• Methyl 2-benzamido-4-(3,4-dimethoxyphenyl)-5-methylbenzoate and<i>N</i>-{5-benzoyl-2-[(<i>Z</i>)-2-methoxyethenyl]-4-methylphenyl}benzamide
  作者：Krištof Kranjc、Marijan Kočevar、Franc Perdih

  DOI：10.1107/s0108270111015794

  日期：2011.6.15

  Methyl 2-benzamido-4-(3,4-dimethoxyphenyl)-5-methylbenzoate, C24H23NO5, (Ia), and N-5-benzoyl-2-[(Z)-2-methoxyethenyl]-4-methylphenyl}benzamide, C24H21NO3, (IIa), were formed via a Diels-Alder reaction of appropriately substituted 2H-pyran-2-ones and methyl propiolate or (Z)-1-methoxybut-1-en-3-yne, respectively. Each of these cycloadditions might yield two different regioisomers, but just one was obtained in each case. In (Ia), an intramolecular N-H center dot center dot center dot O hydrogen bond closes a six-membered ring. A chain is formed due to aromatic pi-pi interactions, and a three-dimensional framework structure is formed by a combination of C-H center dot center dot center dot O and C-H center dot center dot center dot pi(arene) hydrogen bonds. Compound (IIa) was formed not only regioselectively but also chemoselectively, with just the triple bond reacting and the double bond remaining unchanged. Compound (IIa) crystallizes as N-H center dot center dot center dot O hydrogen-bonded dimers stabilized by aromatic pi-pi interactions. Dimers of (IIa) are connected into a chain by weak C-H center dot center dot center dot pi(arene) interactions.
• Diels–Alder reaction of highly substituted 2H-pyran-2-ones with alkynes: reactivity and regioselectivity
  作者：Krištof Kranjc、Marijan Kočevar

  DOI：10.1039/b504852d

  日期：——

  The Diels–Alder reactions of a variety of electron-rich 2H-pyran-2-ones 4 with alkynes 2 yielding aniline derivatives 6 under thermal conditions as well as at high pressures are presented. The effects of the substituents at the positions 3 and 5 in the 2H-pyran-2-one ring on the reactivity and the regioselectivity with different alkynes were qualitatively explained on the basis of electron demand and

  提出了多种富电子的2 H-吡喃-2-酮4与炔2的狄尔斯-阿尔德反应在热条件下以及在高压下的反应，生成苯胺衍生物6。根据电子需求以及通过两性离子中间体的形成，定性地解释了在2 H-吡喃-2-酮环上3和5位的取代基对不同炔烃的反应性和区域选择性的影响。