ethyl 2-(4-methoxybenzoyl)-4-oxo-4-phenylbut-2-enoate | 1422963-93-6

• 分子结构分类: 有机化合物 - 木脂素、新木脂素和相关化合物
• 英文名称: ethyl 2-(4-methoxybenzoyl)-4-oxo-4-phenylbut-2-enoate
• CAS: 1422963-93-6
• 化学式: C₂₀H₁₈O₅
• 分子量: 338.36
• InChiKey: PBGNTLMXXTWNEB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.25
• 重原子数：
  25.0
• 可旋转键数：
  7.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.15
• 拓扑面积：
  69.67
• 氢给体数：
  0.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  ethyl 2-(4-methoxybenzoyl)-4-oxo-4-phenylbut-2-enoate 在 三乙烯二胺 作用下， 以 甲醇 为溶剂， 反应 16.0h， 生成 5-(4-methoxyphenyl)-7-phenylfuro[3,4-d]pyrimidine2,4(1H,3H)-dione
  参考文献：
  名称：

  DABCO 促进的双环化/重排反应从 1,4-烯二酮合成四取代呋喃和呋喃[3,4-d]嘧啶-2,4-二酮

  摘要：

  DABCO 促进的双环化/重排反应已被开发用于合成多取代呋喃，该反应在加热条件下生成呋喃[3,4- d ]嘧啶-2,4-二酮。

  DOI：

  10.1002/ejoc.202300810
• 作为产物：
  描述：

  苯乙酮 、 3-(4-甲氧苯基)-3-氧代丙酸乙酯 在 碘 、 copper(II) oxide 作用下， 以 二甲基亚砜 为溶剂， 反应 12.0h， 生成 ethyl 2-(4-methoxybenzoyl)-4-oxo-4-phenylbut-2-enoate
  参考文献：
  名称：

  Unexpected C–C Bond Cleavage: A Route to 3,6-Diarylpyridazines and 6-Arylpyridazin-3-ones from 1,3-Dicarbonyl Compounds and Methyl Ketones

  摘要：

  An unexpected C-C bond cleavage has been revealed in the absence of metal. This observation has been exploited to develop an efficient approach toward 3,6-iarylpyridazines and 6-arylpyridazin-3-ones from simple and commercially available 1,3-dicarbonyl compounds and methyl ketones.

  DOI：

  10.1021/jo301751e

文献信息

• Auto-tandem catalysis: synthesis of 4H-pyrido[1,2-a]pyrimidin-4-ones via copper-catalyzed aza-Michael addition–aerobic dehydrogenation–intramolecular amidation
  作者：Yan Yang、Wen-Ming Shu、Shang-Bo Yu、Fan Ni、Meng Gao、An-Xin Wu

  DOI：10.1039/c3cc38131e

  日期：——

  A copper-catalyzed domino synthesis of 4H-pyrido[1,2-a]pyrimidin-4-ones has been developed from 1,4-enediones and 2-aminoheterocycles with air as the oxidant.

  铜催化的4H-吡啶并[1,2-a]嘧啶-4-酮的多米诺合成是由1,4-二烯和2-氨基杂环以空气为氧化剂开发的。
• Heterogeneous Cu/OMS-2 as an efficient catalyst for the synthesis of tetrasubstituted 1,4-enediones and 4H-pyrido[1,2-a]-pyrimidin-4-ones
  作者：Jinqi Zhang、Xu Meng、Chaoying Yu、Gexin Chen、Peiqing Zhao

  DOI：10.1039/c5ra17351e

  日期：——

  Copper supported on OMS-2: a heterogeneous catalyst Cu/OMS-2 was prepared for the synthesis of tetrasubstituted 1,4-enediones and 4H-pyrido[1,2-a]-pyrimidin-4-ones under the same conditions with air as the oxidant.

  在OMS-2上支持的铜：制备了一种异质催化剂Cu/OMS-2，用于在空气作为氧化剂的相同条件下合成四取代的1,4-烯二酮和4H-吡啶并[1,2-a]-嘧啶-4-酮。
• Organocatalytic (<i>Z</i>/<i>E</i>)-Selective Synthesis of 3-Vinylnaphthofurans via a Formal (3 + 2) Cycloaddition
  作者：Lei Yu、Ran Xu、Yan-Yi Yao、Yu Lu、Fei-Yang Liu、Wei Tan、Feng Shi

  DOI：10.1021/acs.joc.2c02641

  日期：2023.3.17

  A formal (3 + 2) cycloaddition of 1,4-enediones with 2-naphthols was established under the catalysis of trifluoromethanesulfonic acid as an organocatalyst, leading to the efficient synthesis of structurally diverse 3-vinylnaphthofurans with high yields and excellent (Z/E)-selectivities (up to 96% yield, all >20:1 Z/E). This formal (3 + 2) cycloaddition involved a cascade reaction process, and the intramolecular

  在三氟甲磺酸作为有机催化剂的催化下，建立了 1,4-烯二酮与 2-萘酚的正式 (3 + 2) 环加成反应，高效合成了结构多样的 3-乙烯基萘并呋喃，收率高且性能优异 ( Z / E )-选择性（高达 96% 的产率，均 >20:1 Z / E）。这种形式的 (3 + 2) 环加成涉及级联反应过程，3-乙烯基萘并呋喃结构中的分子内氢键应该在控制 ( Z / E)-新形成的乙烯基的选择性。此外，发现这类 3-乙烯基萘并呋喃具有轴向手性。这项工作提供了一种通过级联反应构建多取代乙烯基萘并呋喃的有机催化方法，具有出色的 ( Z / E )-选择性控制，这将成为通过原位构建呋喃核和形成乙烯基。
• Electronic tuning cyclization of aryl-1,4-enediones: AlCl3-mediated Nazarov-type cyclization to synthesize polysubstituted-1-indanones
  作者：Yan-Ping Zhu、Qun Cai、Feng-Cheng Jia、Mei-Cai Liu、Qing-He Gao、Xiang-Gao Meng、An-Xin Wu

  DOI：10.1016/j.tet.2014.10.052

  日期：2014.12

  An electronic tuning Nazarov-type cyclization protocol was proposed for the synthesis of polysubstituted-1-indanones from the readily available starting materials 1,4-enediones. AlCl3 was highlighted as the most efficient promoter for this reaction. (C) 2014 Elsevier Ltd. All rights reserved.
• Synthesis of Tetrasubstituted Unsymmetrical 1,4-Enediones via Copper-Promoted Autotandem Catalysis and Air As the Oxidant
  作者：Yan Yang、Fan Ni、Wen-Ming Shu、Shang-Bo Yu、Meng Gao、An-Xin Wu

  DOI：10.1021/jo400564f

  日期：2013.6.7

  An efficient procedure has been developed for the preparation of tetrasubstituted unsymmetrical 1,4-enediones via copper-promoted autotandem catalysis and air as the oxidant. Various N-nucleophiles are compatible with this reaction, such as morpholine, piperidine, pyrrolidine, arylamines, pyrazole, imidazole, benzimidazole, and benzotriazole. This reaction also has significant advantages in easily available substrates, atom economy, bond-forming efficiency, and environmental benignity.