(1E,7E)-1,8-Diphenylocta-1,7-diene-3,6-dione | 135468-14-3

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 肉桂酸及其衍生物
• 英文名称: (1E,7E)-1,8-Diphenylocta-1,7-diene-3,6-dione
• 英文别名: (E,E)-1,8-diphenylocta-1,7-diene-3,6-dione；1,8-Diphenyl-1(E),7(E)-octadiene-3,6-dione；1.t.8t-diphenyl-octadiene-(1.7)-dione-(3.6)；1.t.8t-Diphenyl-octadien-(1.7)-dion-(3.6)
• CAS: 135468-14-3
• 化学式: C₂₀H₁₈O₂
• 分子量: 290.362
• InChiKey: WHVCHWVFELJJCG-PHEQNACWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  22
• 可旋转键数：
  7
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.1
• 拓扑面积：
  34.1
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  苄叉丙酮 在 lithium diisopropyl amide 、 copper dichloride 作用下， 以 四氢呋喃 、 正己烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 1.0h， 以28%的产率得到(1E,7E)-1,8-Diphenylocta-1,7-diene-3,6-dione
  参考文献：
  名称：

  WO2008/64060

  摘要：

  公开号：

文献信息

• Synthesis of α,ω‐Bis‐Enones by the Double Addition of Alkenyl Grignard Reagents to Diacid Weinreb Amides
  作者：Stefan Wiesler、Michael A. Bau、Thomas Niepel、Sara L. Younas、Hieu‐Trinh Luu、Jan Streuff

  DOI：10.1002/ejoc.201901043

  日期：2019.9.30

  The synthesis of bis‐enones from alkenyl bromides and α,ω‐bis‐Weinreb amides via a double Grignard reaction is reported. The work contains reliable protocols for the double addition and the efficient generation of the required substituted alkenyl Grignard reagents from alkenyl bromide precursors.

  据报道，通过双格氏反应由链烯基溴化物和α，ω-双-Weinreb酰胺合成双烯酮。这项工作包含可靠的协议，可以从烯基溴化物前体中进行双添加并有效生成所需的取代烯基格利雅试剂。
• Electrochemical and Photocatalytic Oxidative Coupling of Ketones via Silyl Bis-enol Ethers
  作者：Aidan C. Caravana、Benjamin Nagasing、Sandeep Dhanju、Rebekah G. Reynolds、Emily A. Weiss、Regan J. Thomson

  DOI：10.1021/acs.joc.1c00384

  日期：2021.5.7

  Diastereoselective oxidative coupling of ketones through a silyl bis-enol ether intermediate by anodic and photocatalytic oxidation is reported. These methods provide several 1,4-diketones in good yields without the need for stoichiometric metal oxidants. The strategic use of a silicon tether enables the coupling of both aromatic and aliphatic ketones as well as the synthesis of quaternary centers

  报道了通过阳极和光催化氧化通过甲硅烷基双烯醇醚中间体进行酮的非对映选择性氧化偶联。这些方法以良好的收率提供了几种 1,4-二酮，而不需要化学计量的金属氧化剂。硅系链的策略性使用使得芳香族和脂肪族酮的偶联以及四元中心的合成成为可能。循环伏安法用于深入了解反应的氧化事件。
• Synthesis of functionalized tetrahydrofuran derivatives from 2,5-dimethylfuran through cascade reactions
  作者：J. Li、E. Muller、M. Pera-Titus、F. Jérôme、K. De Oliveira Vigier

  DOI：10.1039/c9gc01060b

  日期：——

  its further aldol condensation with aldehydes, and hydrogenation–cyclization of the condensation intermediate to generate alkylated tetrahydrofuran. Active and selective catalysts could be identified for the aldol condensation and hydrogenation–cyclization reactions.

  对于2，5-二甲基呋喃的甲基官能化，提出了一个三步策略，包括2，5-二甲基呋喃与2，5-己二酮的开环，其与醛的进一步的醇醛缩合以及氢化的环化作用。缩合中间体产生烷基化的四氢呋喃。可以确定用于醛醇缩合和加氢-环化反应的活性和选择性催化剂。
• Palladium-Catalyzed Reductive Coupling of Acid Chlorides with .beta.-Stannyl Enones: Synthesis of 1,4-Diketones and Mechanistic Aspects
  作者：Antonio M. Echavarren、Marta Perez、Ana M. Castano、Juan M. Cuerva

  DOI：10.1021/jo00094a032

  日期：1994.7

  The palladium-catalyzed coupling of acid chlorides with (E)-1,2-bis(tri-n-butylstannyl)ethene or beta-stannyl enones gives butane-1,4-diones directly by reduction of the intermediate enedicarbonyl intermediate. The double bond conjugated with a single carbonyl group was not significantly reduced. The generality of the method is illustrated by two syntheses of the 1,4-diketone ipomeanine. By performing the reaction at lower temperatures, alpha,beta-unsaturated 1,4-diketones can also be prepared. The reduction of the intermediate alpha,beta-unsaturated 1,4-diketones probably proceeds by insertion of a palladium hydride, formed in situ by reaction of a Pd(II) complex with Bu(3)SnCl, followed by hydrolysis of the intermediate palladium enolate.
• Facile synthesis of 1,4-diketones via palladium complex catalyzed isomerization of alkynediols
  作者：Xiyan Lu、Jianguo Ji、Dawei Ma、Wei Shen

  DOI：10.1021/jo00020a015

  日期：1991.9

  Alkynediols isomerized under the catalysis of Pd2(dba)3.CHCl3 + 2n-Bu3P in acetonitrile at 80-degrees-C to give 1,4-diketones in high yields. This experimentally simple and economically synthetic method is illustrated with examples including substituents such as alkyl, alkenyl, and aryl groups. The order of reactivity of the substituents in this reaction is aryl greater-than-or-equal-to alkenyl > alkyl. Alkenyl-substituted alkynediols chemoselectively isomerized to the corresponding alpha,beta-unsaturated 1,4-diketones. The usefulness of this novel method is exemplified by the synthesis of dihydrojasmone.