2-acetyl-3-(3-chromonyl)acrylic acid ethyl ester | 57443-89-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并吡喃
• 英文名称: 2-acetyl-3-(3-chromonyl)acrylic acid ethyl ester
• 英文别名: Ethyl 3-oxo-2-[(4-oxochromen-3-yl)methylidene]butanoate
• CAS: 57443-89-7
• 化学式: C₁₆H₁₄O₅
• 分子量: 286.284
• InChiKey: CXYRKTRMKISWJP-UHFFFAOYSA-N

物化性质

• 熔点：
  120-122 °C(Solv: ethanol (64-17-5); water (7732-18-5))
• 沸点：
  392.3±42.0 °C(Predicted)
• 密度：
  1.316±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  21
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.19
• 拓扑面积：
  69.7
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  2-acetyl-3-(3-chromonyl)acrylic acid ethyl ester 在 氟化铵 作用下， 以 甲醇 为溶剂， 反应 6.0h， 以78%的产率得到2-methyl-5-(2-hydroxybenzoyl)nicotinic acid ethyl ester
  参考文献：
  名称：

  Reagent-controlled domino synthesis of skeletally-diverse compound collections

  摘要：

  已开发出一种高效的试剂控制方法，可通过共用底物生成高度取代的多样性骨架；因此，使用不同的脱硅试剂（如氟化铵、氟化铯和PPTS）处理共用前体，会引发不同的多米诺反应序列，分别生成高度取代的吡啶、酚和苯并吡喃；这些骨架的取代模式为文库开发提供了进一步的机会。

  DOI：

  10.1039/b717635j
• 作为产物：
  描述：

  乙酰乙酸乙酯 、 色酮-3-甲醛 在 乙酸酐 、 potassium carbonate 作用下， 反应 0.67h， 以39%的产率得到2-acetyl-3-(3-chromonyl)acrylic acid ethyl ester
  参考文献：
  名称：

  Metal-Free Cascade Approach toward Polysubstituted Indolizines from Chromone-Based Michael Acceptors

  摘要：

  An efficient cascade transformation toward indolizine-based molecules has been developed. This process leads to the rapid construction of two C-N bonds and one C-C bond without the need of any metal catalysis. The approach involves easily accessible chromone-based Michael acceptors and propargylamine derivatives as starting materials. This cascade constitutes a novel and very competitive alternative to the well reported strategies using pyridine or pyrrole derivatives for accessing the indolizine ring with substituents at uncommon C-positions

  DOI：

  10.1021/acs.orglett.7b00309

文献信息

• Benzopyrans. Part 42. Reactions of 4-Oxo-4<i>H</i>-1-benzopyran-3-carbaldehyde with some active methylene compounds in the presence of ammonia
  作者：Chandra Kanta Ghosh、Anirban Ray、Amarendra Patra

  DOI：10.1002/jhet.5570380632

  日期：2001.11

  The title aldehyde 1 in the presence of ammonia gives the pyridine derivatives 9-11 respectively with acetylacetone, diethyl malonate and ethyl cyanoacetate, and ethyl (or methyl)-l-benzopyrano[4,3-b]pyri-dine-3-carboxylate 22 (or 23) with ethyl (or methyl) acetoacetate. Acetylacetone pretreated with ammonia condenses with 1 giving the fused pyridine 24. Ammonia converts the ester 6 to the pyridine

  在氨存在下的标题醛1分别与乙酰丙酮，丙二酸二乙酯和氰基乙酸乙酯，以及（或甲基）-1-苯并吡喃并[4,3 - b ]吡啶-丁-3-羧酸酯分别给出吡啶衍生物9-11 22（或23）用乙酰乙酸乙酯（或甲基）。用氨预处理的乙酰丙酮与1缩合，得到稠合的吡啶24。氨将酯6转化为吡啶13或14。22和23的铬酸氧化分别提供香豆素吡啶25和26。
• Simple and ecofriendly synthesis of dihydropyrimidinones (thiones), dihydropyridines, and pyridines using 3-formylchromones as substrates assisted by a recyclable Preyssler heteropolyacid
  作者：Laura M. Sanchez、Gustavo Pasquale、Ángel Sathicq、Diego Ruiz、Jorge Jios、Andrea L. Ferreira de Souza、Gustavo P. Romanelli

  DOI：10.1002/hc.21340

  日期：2016.9

  Several dihydropyrimidinones/thiones, 1,4-dihydropyridines, and pyridine derivatives were prepared in very good yields and purity values. The corresponding reactions were carried out by employing a bulk Preyssler heteropolyacid H14[NaP5W29MoO110] as an efficient and recyclable catalyst. The preparation of pyridine derivatives was carried out not through a usual procedure, i.e., the opening of the γ-pyrone

  以非常好的产率和纯度值制备了几种二氢嘧啶酮/硫酮、1,4-二氢吡啶和吡啶衍生物。相应的反应是通过使用本体 Preyssler 杂多酸 H14[NaP5W29MoO110] 作为有效且可回收的催化剂进行的。吡啶衍生物的制备不是通过通常的程序进行的，即3-甲酰基色酮的γ-吡喃酮环的开环。通常，反应在 80°C 的无溶剂条件下进行，反应时间很短。
• Hass, Georges; Stanton, James L.; Sprecher, Andreas von, Journal of Heterocyclic Chemistry, 1981, vol. 18, p. 607 - 612
  作者：Hass, Georges、Stanton, James L.、Sprecher, Andreas von、Wenk, Paul

  DOI：——

  日期：——
• Bandyopadhyay, Chandrakanta; Nag, Partha Pratim; Sur, Kumar Ranabir, Journal of the Indian Chemical Society, 2004, vol. 81, # 2, p. 132 - 136
  作者：Bandyopadhyay, Chandrakanta、Nag, Partha Pratim、Sur, Kumar Ranabir、Patra, Ranjan、Banerjee, Subhabrata、Sen, Arunabha、Ghosh, Tapas

  DOI：——

  日期：——
• Metal-Free Cascade Approach toward Polysubstituted Indolizines from Chromone-Based Michael Acceptors
  作者：Thomas Lepitre、Raphael Le Biannic、Mohamed Othman、Ata Martin Lawson、Adam Daïch

  DOI：10.1021/acs.orglett.7b00309

  日期：2017.4.21

  An efficient cascade transformation toward indolizine-based molecules has been developed. This process leads to the rapid construction of two C-N bonds and one C-C bond without the need of any metal catalysis. The approach involves easily accessible chromone-based Michael acceptors and propargylamine derivatives as starting materials. This cascade constitutes a novel and very competitive alternative to the well reported strategies using pyridine or pyrrole derivatives for accessing the indolizine ring with substituents at uncommon C-positions