1,2,3,4-tetraphenyl-1,3-butadiene | 806-71-3

• 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: 1,2,3,4-tetraphenyl-1,3-butadiene
• 英文别名: buta-1,3-diene-1,2,3,4-tetrayltetrabenzene；1,2,3,4-tetraphenyl-buta-1,3-diene；1,2,3,4-Tetraphenyl-buta-1,3-dien；1,2,3,4-Tetraphenyl-butadien-(1,3)；1,2,3,4-Tetraphenyl-butadien-1,3；cis,trans-Tetraphenylbutadien；1,2,3,4-Tetraphenyl-1,3-butadien；1,3,4-triphenylbuta-1,3-dien-2-ylbenzene
• CAS: 806-71-3
• 化学式: C₂₈H₂₂
• 分子量: 358.483
• InChiKey: DAABVBOFAIYKNX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8.6
• 重原子数：
  28
• 可旋转键数：
  5
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  0
• 氢给体数：
  0
• 氢受体数：
  0

反应信息

• 作为反应物：
  描述：

  1,2,3,4-tetraphenyl-1,3-butadiene 在 sulfur 作用下， 生成 四苯基噻吩
  参考文献：
  名称：

  The Reaction between Lithium and Diphenylacetylene

  摘要：

  DOI：

  10.1021/ja01850a006
• 作为产物：
  描述：

  联苯甲酰 在 乙醚 、 乙酰氯 作用下， 生成 1,2,3,4-tetraphenyl-1,3-butadiene
  参考文献：
  名称：

  Orechow, Chemische Berichte, 1914, vol. 47, p. 91

  摘要：

  DOI：

文献信息

• Mechanistic Comparison of the Nickel(0)-Catalyzed Homo-Oligomerization and Co-Oligomerization of Alkynes and Nitriles
  作者：John J. Eisch、Xin Ma、Kyoung I. Han、John N. Gitua、Carl Krüger

  DOI：10.1002/1099-0682(20011)2001:1<77::aid-ejic77>3.0.co;2-g

  日期：2001.1

  co-oligomerization of diphenylacetylene and benzonitrile with ordinary nickel(0) complexes led only to the homocyclotrimer of the alkyne. Only when the alkyne was prebonded to the nickel, as in (Bpy)(PhC≡N)Ni, could significant amounts of a codimerization product with the nitrile be observed. The origin of the triazine, claimed in a previous report to form from benzonitrile and Raney nickel, has been traced

  已经对镍 (0) 催化的炔烃和腈的均聚和共聚低聚进行了比较机理研究，使用二苯乙炔和苯甲腈，针对一系列镍 (0) 试剂，例如细碎的镍，（ COD)2Ni、(Bpy)(COD)Ni、(Et3P)4Ni、(Bpy)(PhC≡CPh)Ni 和 (COD)2Ni-MeAlCl2 在供体 (THF) 和非供体（PhMe 或纯底物）溶剂中的组合。特别关注初始 1:1 加合物 (Bpy)(PhC≡CPh)Ni、(Ph3P)3(PhC≡CPh)Ni 和 [(Ph3P)(PhC≡N)Ni] 的详细分子结构4 通过 XRD 和 IR 数据的考虑。此处首次报道的 (Bpy)(PhC≡CPh)Ni 单晶 XRD 分析数据显示与 2 的存在非常一致，(PhC≡CPh)Ni 部分的 3-二苯基镍环丙烯环与联吡啶配体的几乎共面螯合配位，而不是炔烃与金属中心的简单“侧向”配位。从以前的出版物中提取的两种苯甲腈-镍 (0) 配合物的
• Palladium catalysed alkyne hydrogenation and oligomerisation: a parahydrogen based NMR investigation
  作者：Joaquín López-Serrano、Simon B. Duckett、John P. Dunne、Cyril Godard、Adrian C. Whitwood

  DOI：10.1039/b804162h

  日期：——

  The role phosphine ligands play in the palladium(II)-bis-phosphine-hydride cation catalysed hydrogenation of diphenylacetylene is explored through a PHIP (parahydrogen induced polarization) NMR study. The precursors Pd(LL′)(OTf)2 (1a–e) [LL′ = dcpe (PCy2CH2CH2PCy2), dppe, dppm, dppp, cppe (PCy2CH2CH2PPh2)] are used. Alkyl palladium intermediates of the type [Pd(LL′)(CHPhCH2Ph)](OTf) (2 and 3) are detected and demonstrated to play an active role in hydrogenation catalysis. Magnetization transfer experiments reveal chemical exchange from the α-H of the alkyl ligand of 2a (LL′ = dcpe) and linkage isomer 2e′ (LL′ = cppe) into trans-stilbene on the NMR timescale. Activation parameters (ΔH≠ and ΔS≠) for this transformation have been determined. These experiments, coupled with GC/MS data, indicate that the catalytic activity is greater in methanol, where it follows the order: dcpe > cppe > dppp > dppe > dppm, than in CD2Cl2. All five of the phosphine systems described are less active than those based on bcope [where bcope is (C8H14)PCH2–CH2P(C8H14)] and tbucope [where tbucope is (C8H14)PC6H4CH2P(tBu)2]. cis, cis-1,2,3,4-Tetraphenyl-buta-1,3-diene is detected as a minor reaction product with Pd(LL′)(PhCH–CHPh–CPhCHPh)+ (4) also being shown to play a role in the alkyne dimerisation step.

  通过PHIP（对氢诱导极化）NMR研究探讨了膦配体在钯(II)-双膦-氢阳离子催化苯基乙炔氢化反应中的作用。使用的前体为Pd(LL′)(OTf)₂（1a-e）[LL′ = dcpe（PCy₂CH₂CH₂PCy₂），dppe，dppm，dppp，cppe（PCy₂CH₂CH₂PPh₂）]。检测到类型为[Pd(LL′)(CHPhCH2Ph)](OTf)（2和3）的烷基钯中间体，并证明其在氢化催化中发挥了积极作用。磁化转移实验揭示了来自2a（LL′ = dcpe）和连接异构体2e′（LL′ = cppe）烷基配体的α-H在NMR时间尺度上与反式stilbene之间的化学交换。已确定该转化的活化参数（ΔH≠和ΔS≠）。这些实验结合GC/MS数据表明，在甲醇中催化活性更强，顺序为：dcpe > cppe > dppp > dppe > dppm，相比之下在CD₂Cl₂中活性较低。所描述的五种膦配体系统的活性均低于基于bcope（其中bcope为(C₈H₁₄)PCH₂–CH₂P(C₈H₁₄)）和tbucope（其中tbucope为(C₈H₁₄)PC₆H₄CH₂P(tBu)₂）的系统。检测到顺-顺-1,2,3,4-四苯基-丁-1,3-二烯作为次要反应产物，同时Pd(LL′)(PhCH–CHPh–CPhCHPh)⁺（4）在炔烃二聚化步骤中也显示出作用。
• Synthesis of Indenes via Brønsted Acid Catalyzed Cyclization of Diaryl- and Alkyl Aryl-1,3-dienes
  作者：Dahan Eom、Sangjune Park、Youngchul Park、Taekyu Ryu、Phil Ho Lee

  DOI：10.1021/ol302271w

  日期：2012.11.2

  Substituted indenes can be synthesized via the Brønsted acid catalyzed cyclization of diaryl- and alkyl aryl-1,3-dienes. In this approach, treatment of symmetric or unsymmetric diaryl- and alkyl aryl-1,3-dienes with a catalytic amount of trifluoromethanesulfonic acid gives a variety of indene derivatives in good to excellent yields under mild conditions.

  取代的茚满可以通过布朗斯台德酸催化的1，3-二芳基二芳基和烷基芳基的环化反应合成。在这种方法中，用催化量的三氟甲磺酸处理对称或不对称的二芳基和烷基芳基-1,3-二烯可在温和的条件下以良好或优异的收率得到各种茚衍生物。
• Birch Reductions at Room Temperature with Alkali Metals in Silica Gel (Na₂K-SG(I))
  作者：Partha Nandi、James L. Dye、James E. Jackson

  DOI：10.1021/jo900904f

  日期：2009.8.21

  Alkali metals in silica gel (the Na2K-SG(I) reagent) cleanly effect Birch reductions of substrates with at least two or more aromatic rings. The reaction conditions are alcohol-free, ammonia-free, and achieve excellent yields and high selectivities at room temperature.

  硅胶中的碱金属（Na 2 K-SG（I）试剂）可以干净地实现具有至少两个或多个芳香环的底物的桦木还原。该反应条件是无醇，无氨的，在室温下可获得优异的收率和高选择性。
• Contrasting Photochemical and Thermal Catalysis by Ruthenium Arsine Complexes Revealed by Parahydrogen Enhanced NMR Spectroscopy
  作者：Ralph W. Adams、Richard O. John、Damir Blazina、Beatriz Eguillor、Martin C. R. Cockett、John P. Dunne、Joaquín López‐Serrano、Simon B. Duckett

  DOI：10.1002/ejic.202100991

  日期：2022.2.16

  The thermal and photochemical reactivity of Ru(CO)3(dpae) (1) and Ru(CO)2(dpae)(PPh3) (2) towards diphenylacetylene is probed by NMR with parahydrogen. Several reactive species including Ru(CO)2(dpae)(η2-CHPh=CPhCPh=CHPh), Ru(CHPhCH2Ph)(H)(CO)2(dpae) and Ru(CO)2(dpae)(trans-stilbene) are seen.

  Ru(CO) 3 (dpae) ( 1 ) 和Ru(CO) 2 (dpae)(PPh 3 ) ( 2 ) 对二苯乙炔的热和光化学反应性通过NMR与仲氢进行了探测。几种反应性物质包括Ru(CO) 2 (dpae)(η 2 -CHPh=CPhCPh=CHPh)、Ru(CHPhCH 2 Ph)(H)(CO) 2 (dpae)和Ru(CO) 2 (dpae)(反式-芪) 可见。