n-butyl (E,E)-5-phenylpenta-2,4-dienoate

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: n-butyl (E,E)-5-phenylpenta-2,4-dienoate
• 英文别名: butyl (2E,4E)-5-phenylpenta-2,4-dienoate；butyl (E,E)-5-phenylpenta-2,4-dienoate；(2E,4E)-butyl 5-phenylpenta-2,4-dienoate
• 化学式: C₁₅H₁₈O₂
• 分子量: 230.307
• InChiKey: JFGSFMXIVFQEST-MKICQXMISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.1
• 重原子数：
  17
• 可旋转键数：
  7
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  丙烯酸丁酯 、 [(Z)-2-溴乙烯基]苯 在 bis(η3-allyl-μ-chloropalladium(II)) potassium carbonate 、 顺式,顺式,顺式-1,2,3,4-四[(二苯基膦)甲基]环戊烷 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 20.0h， 以95%的产率得到n-butyl (E,E)-5-phenylpenta-2,4-dienoate
  参考文献：
  名称：

  Berthiol, Florian; Doucet, Henri; Santelli, Maurice, Synlett, 2003, # 6, p. 841 - 844

  摘要：

  DOI：

文献信息

• Ruthenium-Catalyzed Oxidative Cross-Coupling Reaction of Activated Olefins with Vinyl Boronates for the Synthesis of (<i>E</i>,<i>E</i>)-1,3-Dienes
  作者：Dattatraya H. Dethe、Nagabhushana C. Beeralingappa、Amar Uike

  DOI：10.1021/acs.joc.0c02823

  日期：2021.2.19

  An oxidative cross-coupling reaction between activated olefins and vinyl boronate derivatives has been developed for the highly stereoselective construction of synthetically useful (E,E)-1,3-dienes. The highlight of this reaction is that exclusive stereoselectivity (only E,E-isomer) was achieved from a base-free, ligand-free, and mild catalytic condition with a less expensive [RuCl2(p-cymene)]2 catalyst

  已经开发出活化烯烃和乙烯基硼酸酯衍生物之间的氧化交叉偶联反应，以用于合成有用的（E，E）-1，3-二烯的高度立体选择性的结构。该反应的亮点在于，使用便宜的[RuCl 2（p- Cymene）] 2催化剂，可从无碱，无配体和温和的催化条件下获得独特的立体选择性（仅E，E-异构体）。
• Palladium-Tetraphosphine Complex Catalysed Heck Reaction of Vinyl Bromides with Alkenes: A Powerful Access to Conjugated Dienes
  作者：Henri Doucet、Maurice Santelli、Mhamed Lemhadri、Ahmed Battace、Florian Berthiol、Touriya Zair

  DOI：10.1055/s-2008-1032124

  日期：——

  A wide variety of 1,3-dienes have been prepared by the Heck vinylation of vinyl bromides using [Pd(η 3 -C 3 H 5 )Cl] 2 / CIS, CIS, CIS-1,2,3,4-tetrakis[(diphenylphosphino)methyl]cyclopentane (Tedicyp) as the catalyst precursor. Both α- and β-substituted vinyl bromides undergo the Heck reaction with functionalised alkenes such as acrylates, enones, styrenes or a vinyl sulfone, and also with nonfunctionalised

  使用 [Pd(η 3 -C 3 H 5 )Cl] 2 / CIS, CIS, CIS-1,2,3,4-tetrakis 通过乙烯基溴化物的 Heck 乙烯基化制备了多种 1,3-二烯[(二苯基膦基)甲基]环戊烷(Tedicyp)作为催化剂前体。α- 和 β- 取代的溴化乙烯都与官能化烯烃（如丙烯酸酯、烯酮、苯乙烯或乙烯基砜）以及非官能化烯烃（如 dec-1-ene）发生 Heck 反应，在大多数情况下，立体选择性导致相应的 E- 或 E, E-1,3-二烯，收率良好。此外，这种催化剂可以在低负载下用于多种反应。
• Ruthenium/Halide Catalytic System for CC Bond Forming Reaction between Alkynes and Unsaturated Carbonyl Compounds
  作者：Takahiro Nishimura、Yosuke Washitake、Sakae Uemura

  DOI：10.1002/adsc.200700371

  日期：2007.12.10

  with alkyl acrylates proceeds in the presence of a catalytic amount of Ru3(CO)12 and lithium iodide to give the corresponding conjugate dienes. These two different types of catalytic carbon-carbon bond forming reactions are controlled only by the nature of halide ions, either a chloride or an iodide, with other conditions being kept almost the same.

  在双（三苯基膦）亚甲基氯化铵（[PPN] Cl）存在下的钌络合物[十二碳三钌，Ru 3（CO）12 ]催化末端炔烃向丙烯酸烷基酯的共轭加成反应，从而获得高产率的γ，δ-炔基酯。另一方面，末端炔与丙烯酸烷基酯的线性共聚反应在催化量的Ru 3（CO）12和碘化锂的存在下进行，得到相应的共轭二烯。这两种不同类型的催化碳-碳键形成反应仅受卤离子（氯离子或碘离子）的性质控制，其他条件几乎保持不变。
• Pd(II)-Catalyzed Dehydrogenative Olefination of Vinylic C–H Bonds with Allylic Esters: General and Selective Access to Linear 1,3-Butadienes
  作者：Yuexia Zhang、Zili Cui、Zejiang Li、Zhong-Quan Liu

  DOI：10.1021/ol300442w

  日期：2012.4.6

  dienes by Pd(II)-catalyzed direct olefination of unactivated alkenes with allylic esters and acrylates via vinylic C–H activation. Various aryl and heteroaryl alkenes as well as aliphatic alkenes all give the desired linear 1,3-butadienes with retention of the traditional leaving groups such as OAc and other carboxylic acid ester groups.

  这项工作展示了一种通用而有效的方法，该方法通过Pd（II）催化未活化烯烃与烯丙基酯和丙烯酸酯的乙烯基C–H活化而被直接活化，以制备共轭二烯。各种芳基和杂芳基烯烃以及脂族烯烃都得到所需的直链1，3-丁二烯，同时保留了传统的离去基团，如OAc和其他羧酸酯基团。
• Mizoroki−Heck Type Reaction of Organoboron Reagents with Alkenes and Alkynes. A Pd(II)-Catalyzed Pathway with Cu(OAc)₂ as an Oxidant
  作者：Xiaoli Du、Masahiro Suguro、Kazunori Hirabayashi、Atsunori Mori、Takashi Nishikata、Nobuhito Hagiwara、Kentaro Kawata、Takeaki Okeda、Hui Feng Wang、Keigo Fugami、Masanori Kosugi

  DOI：10.1021/ol016529y

  日期：2001.10.1

  [GRAPHICS]In contrast to the Pd(0)-catalyzed mechanism by Uemura, Mizoroki-Heck type reaction of boronic acids is found to proceed under a Pd(ll)mediated pathway using a catalytic amount of Pd(OAc)(2) in the presence of Cu(OAc)(2) as an oxidant. Treatment of a variety of alkenes with boronic acids, boronates, and sodium tetraphenylborate furnishes beta -arylated and alkenylated products in good to excellent yields. The reactions with norbornene, norbornadiene, and diphenylacetylene are also performed to give 1:2 or 2:1 coupling products.