(3-(4-methoxyphenyl)penta-1,4-diyne-1,5-diyl)dibenzene

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 直链 1,3-二芳基丙烷
• 英文名称: (3-(4-methoxyphenyl)penta-1,4-diyne-1,5-diyl)dibenzene
• 英文别名: 1-(1,5-Diphenylpenta-1,4-diyn-3-yl)-4-methoxybenzene；1-(1,5-diphenylpenta-1,4-diyn-3-yl)-4-methoxybenzene
• 化学式: C₂₄H₁₈O
• 分子量: 322.406
• InChiKey: GQLZRJNJLZWCFJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.1
• 重原子数：
  25
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.08
• 拓扑面积：
  9.2
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为产物：
  描述：

  4-甲氧基苯甲醛 、 苯基乙炔基三甲基硅烷 在 三氟甲磺酸三甲基硅酯 、 (C₆H₅C₆H₄((CH₃)3C)2P)AuCCC₆H₅ 作用下， 以 1,2-二氯乙烷 为溶剂， 反应 1.25h， 以73%的产率得到(3-(4-methoxyphenyl)penta-1,4-diyne-1,5-diyl)dibenzene
  参考文献：
  名称：

  金（I）催化的芳香醛与炔基硅烷的双炔基化反应

  摘要：

  AbstractThe first successful gold(I)‐catalyzed reaction of aryl aldehydes with trimethyl(arylethynyl)silanes to furnish bis‐alkynylated derivatives is reported. Key CC bond‐forming events involved in the catalytic cycle are analyzed.magnified image

  DOI：

  10.1002/adsc.201300578

文献信息

• Redox and Lewis Acid Relay Catalysis: A Titanocene/Zinc Catalytic Platform in the Development of Multicomponent Coupling Reactions
  作者：Joseph B. Gianino、Catherine A. Campos、Antonio J. Lepore、David M. Pinkerton、Brandon L. Ashfeld

  DOI：10.1021/jo501890z

  日期：2014.12.19

  A titanocene-catalyzed multicomponent coupling is described herein. Using catalytic titanocene, phosphine, and zinc dust, zinc acetylides can be generated from the corresponding iodoalkynes to affect sequential nucleophilic additions to aromatic aldehydes. The intermediate propargylic alkoxides are trapped in situ with acetic anhydride, which are susceptible to a second nucleophilic displacement upon

  本文描述了钛茂催化的多组分偶联。使用催化的钛茂，膦和锌粉，可以从相应的碘代炔烃生成乙炔锌，从而影响向芳香族醛的连续亲核加成。中间体炔丙基醇盐被原位捕获用乙酸酐，乙酸酐在用各种富含电子的物质处理后易发生第二次亲核取代，这些富含电子的物质包括乙炔化物，烯丙基硅烷，富电子芳族化合物，甲硅烷基烯醇醚和甲硅烷基烯酮缩醛。另外，使用环丙烷甲醛导致碘掺入导致开环产物。综上所述，这些结果构成了三组分偶联反应新模式的基础，该模式允许在单个合成操作中快速获得增值产品。
• Aryl Aldehydes as Traceless Dielectrophiles in Bifunctional Titanocene-Catalyzed Propargylic C–X Activations
  作者：Catherine A. Campos、Joseph B. Gianino、David M. Pinkerton、Brandon L. Ashfeld

  DOI：10.1021/ol202401n

  日期：2011.10.21

  directly from aromatic aldehydes is described. The starting aldehyde behaves as a traceless functionality in the formation of multiple carbon–carbon bonds through consecutive carbon–heteroatom bond activations. The sequential addition of a metal acetylide and a second carbon nucleophile to the dielectrophilic aldehyde enables the construction of symmetrical and unsymmetrical 1,4-diynes in good yields

  描述了直接由芳族醛进行钛碳烯催化的全碳取代的叔中心的结构。起始醛通过连续的碳-杂原子键激活，在形成多个碳-碳键时表现为无痕的功能。将金属乙炔化物和第二个碳亲核试剂顺序地添加到该二亲电子醛中使得能够以良好的产率构建对称和不对称的1，4-二炔。
• AuPPh3Cl/AgOTf-catalyzed reaction of terminal alkynes: nucleophilic addition to activated C O bond
  作者：Changkun Li、Fanyang Mo、Weibin Li、Jianbo Wang

  DOI：10.1016/j.tetlet.2009.08.049

  日期：2009.11

  Terminal alkynes, under Au-catalyzed conditions, react with aromatic aldehyde diethyl acetals, affording propargylation products through C=O bond addition. Furthermore, AuPPh3Cl/AgOTf-catalyzed three-component reaction of aldehydes, alkynes, and triethyl orthoformate is developed. Gold alkynilides are supposed to be reactive intermediates in these reactions. (C) 2009 Elsevier Ltd. All rights reserved.
• Rhenium- and Gold-Catalyzed Coupling of Aromatic Aldehydes with Trimethyl(phenylethynyl)silane: Synthesis of Diethynylmethanes
  作者：Yoichiro Kuninobu、Eri Ishii、Kazuhiko Takai

  DOI：10.1002/anie.200700183

  日期：2007.4.27
• Gold(I)-Catalyzed Bis-Alkynylation Reaction of Aromatic Aldehydes with Alkynylsilanes
  作者：Belén Rubial、Alfredo Ballesteros、José M. González

  DOI：10.1002/adsc.201300578

  日期：2013.11.25

  AbstractThe first successful gold(I)‐catalyzed reaction of aryl aldehydes with trimethyl(arylethynyl)silanes to furnish bis‐alkynylated derivatives is reported. Key CC bond‐forming events involved in the catalytic cycle are analyzed.magnified image