2-benzoyl-1,4-diphenylbut-2-ene-1,4-dione | 102596-02-1

• 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: 2-benzoyl-1,4-diphenylbut-2-ene-1,4-dione
• 英文别名: 1,1,2-Tribenzoylethylene
• CAS: 102596-02-1
• 化学式: C₂₃H₁₆O₃
• 分子量: 340.378
• InChiKey: AMPWOQJJRKCGQT-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.7
• 重原子数：
  26
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  51.2
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2-benzoyl-1,4-diphenylbut-2-ene-1,4-dione 在 一水合肼 作用下， 以 叔丁醇 为溶剂， 以176.3 mg的产率得到3,6-二苯基哒嗪
  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
• 作为产物：
  描述：

  2-碘-1-苯基乙酮 在 N-氯代丁二酰亚胺 、 copper(l) iodide 、 对甲苯磺酸 作用下， 以 二甲基亚砜 、 乙腈 为溶剂， 反应 1.0h， 生成 2-benzoyl-1,4-diphenylbut-2-ene-1,4-dione
  参考文献：
  名称：

  Target-oriented synthesis: miscellaneous synthetic routes to access 1,4-enediones through the coupling of 1,3-dicarbonyl compounds with multiform substrates

  摘要：

  Target-oriented synthetic protocol was presented for the synthesis of 1,4-enediones. The approach can efficiently construct 1,4-enediones through different reaction pathways from multiform substrates alpha-halo aromatic ketones, 2-hydroxy-aromatic ketones and methyl carbinols. In this reaction, CuI was found to be the most efficient catalyst. Multiform substrates were also found to perform well to afford the products in a one-pot fashion. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2013.05.106

文献信息

• An Expedient, Direct, Three-Component Approach for the Synthesis of 4-Thioarylpyrroles
  作者：Venkatachalam Rajeshkumar、Chinnaraj Neelamegam、Sambandam Anandan

  DOI：10.1055/s-0039-1690024

  日期：2019.11

  corresponding sulfoxide and sulfone. A three-component strategy for the synthesis of 4-thioarylpyrroles from 1,4-enediones, thiols, and ammonium formate in one-pot has been developed. The reaction proceeds through the sequential thiol-Michael/Paal–Knorr reaction of 1,4-enediones with the formation of one new C–S and two C–N bonds. The operationally simple protocol provides direct access to the highly functionalized

  抽象的 已经开发了一种由一锅法由1，4-二烯，硫醇和甲酸铵合成4-硫代芳基吡咯的三组分策略。该反应通过1，4-二烯的顺序硫醇-迈克尔/帕尔-克诺尔反应进行，并形成一个新的C-S和两个C-N键。该操作简单的方案可以良好的产率直接获得具有游离NH的高度官能化的4-硫代芳基吡咯。通过将硫原子氧化成相应的亚砜和砜，证明了合成的4-硫代芳基吡咯的合成应用。 已经开发了一种由一锅法由1，4-二烯，硫醇和甲酸铵合成4-硫代芳基吡咯的三组分策略。该反应通过1，4-二烯的顺序硫醇-迈克尔/帕尔-克诺尔反应进行，并形成一个新的C-S和两个C-N键。该操作简单的方案可以良好的产率直接获得具有游离NH的高度官能化的4-硫代芳基吡咯。通过将硫原子氧化成相应的亚砜和砜，证明了合成的4-硫代芳基吡咯的合成应用。
• Efficient approach to 2-hydroxy-2,3-dihydrofuran derivatives and its application for the synthesis of novel 4-(1H-pyrazol-4-yl)pyridazines
  作者：Jun-Rui Ma、Wen-Ming Shu、Kai-Lu Zheng、Fan Ni、Guo-Dong Yin、An-Xin Wu

  DOI：10.1039/c5ob00163c

  日期：——

  A highly efficient method for the synthesis of 2-hydroxy-2,3-dihydrofuran derivatives from 1,4-enediones and phenacyl pyridinium halides via a domino reaction has been developed. This is a simple and beneficial strategy for the construction of 2-hydroxy-2,3-dihydrofuran compounds from readily available starting materials under mild conditions. Moreover, the application of this reaction provides a straightforward

  已经开发了一种通过多米诺反应从1，4-二酮和苯甲酰基吡啶鎓卤化物合成2-羟基-2,3-二氢呋喃衍生物的高效方法。这是在温和条件下由容易获得的起始原料构建2-羟基-2,3-二氢呋喃化合物的简单而有益的策略。而且，该反应的应用为合成新型的4-（1H-吡唑-4-基）哒嗪骨架提供了直接而实用的途径。
• Copper-Catalyzed Domino Synthesis of 2-Imino-1<i>H</i>-imidazol-5(2<i>H</i>)-ones and Quinoxalines Involving CC Bond Cleavage with a 1,3-Dicarbonyl Unit as a Leaving Group
  作者：Yan Yang、Fan Ni、Wen-Ming Shu、An-Xin Wu

  DOI：10.1002/chem.201403001

  日期：2014.9.8

  The domino sequence for the synthesis of 2‐imino‐1H‐imidazol‐5(2H)‐ones includes aza‐Michael addition, intramolecular cyclization, CC bond‐cleavage, 1,2‐rearrangement, and aerobic dehydrogenation reaction, whereas the domino sequence for the synthesis of quinoxalines includes aza‐Michael addition, intramolecular cyclization, elimination reaction, and CC bond‐cleavage reaction. The two domino reactions

  尽管2-亚氨基-1 H-咪唑-5（2 H）-酮在代谢中具有重要的生物学活性，但很少对其合成进行研究。喹喔啉作为药物化学中的“特权支架”已被广泛研究，但是新型有效合成方法的开发仍然非常有吸引力。本文中，我们开发了两个铜催化的多米诺反应，用于合成2–亚氨基-1 H-咪唑-5（2 H）-ones和喹喔啉，涉及CC键断裂，并带有1,3-二羰基单元。离开小组。合成2-亚氨基1 H-咪唑5（2 H）-1的多米诺序列包括aza-Michael加成，分子内环化，C C键裂解，1,2-重排，和有氧脱氢反应，而对于喹喔啉的合成的多米诺序列包括氮杂-迈克尔加成，分子内环化，消除反应，和C  C键断裂反应。这两个多米诺反应具有显着的优势，包括高效，温和的反应条件以及对各种官能团的高度耐受性。
• Formation of Unsymmetrical 1,4-Enediones via A Focusing Domino Strategy: Cross-Coupling of 1,3-Dicarbonyl Compounds and Methyl Ketones or Terminal Aryl Alkenes
  作者：Meng Gao、Yan Yang、Yan-Dong Wu、Cong Deng、Li-Ping Cao、Xiang-Gao Meng、An-Xin Wu

  DOI：10.1021/ol100473f

  日期：2010.4.16

  A highly efficient synthesis of unsymmetrical 1,4-enediones from 1,3-dicarbonyl compounds and methyl ketones or terminal aryl alkenes has been developed via a focusing domino strategy. Simple and readily available starting materials, mild reaction conditions, and a very simple operation are advantages of the reaction, which allow straightforward synthesis of a variety of unsymmetrical 1,4-enediones

  通过聚焦多米诺骨牌战略已开发出一种由1,3-二羰基化合物和甲基酮或末端芳基烯烃高效合成不对称1,4-二烯键的方法。简单且容易获得的起始原料，温和的反应条件和非常简单的操作是反应的优势，可以直接合成各种不对称的1,4-二烯酮。
• Highly Efficient Synthesis of 3a,6a-Dihydrofuro[2,3-<i>b</i>]furans via a Novel Bicyclization
  作者：Wen-Ming Shu、Yan Yang、Dong-Xue Zhang、Liu-Ming Wu、Yan-Ping Zhu、Guo-Dong Yin、An-Xin Wu

  DOI：10.1021/ol400016c

  日期：2013.2.1

  A highly efficient method for the construction of 3a,6a-dihydrofuro[2,3-b]furan derivatives has been developed via a novel bicyclization, which is very valuable for the synthesis of fused furofuran compounds since it is time-saving and catalyst-free. Based on the bicyclization, a coupled domino strategy has been developed to directly construct 3a,6a-dihydrofuro[2,3-b]furan derivatives from methyl ketones

  通过新型的双环化，已经开发出了一种高效的3a，6a-二氢呋喃[2,3- b ]呋喃衍生物的构建方法，该方法对于合成熔融呋喃呋喃化合物非常节省时间，并且可以催化催化剂。自由。基于双环化，已开发了一种耦合多米诺骨牌策略，可直接从甲基酮构建3a，6a-二氢呋喃[2,3- b ]呋喃衍生物。