(E)-1,3,7-octatriene | 26198-79-8

• 分子结构分类: 有机化合物 - 碳氢化合物 - 不饱和烃
• 英文名称: (E)-1,3,7-octatriene
• 英文别名: 1,3,7-octatriene；1,3E,7-octatriene；(E)-octa-1,3,7-triene；1,3,7-Octatrien；n-Octatrien (1,3,7)；trans-Octatrien-(1,3,7)；octa-1,3,7-triene；(3E)-octa-1,3,7-triene
• CAS: 26198-79-8
• 化学式: C₈H₁₂
• 分子量: 108.183
• InChiKey: ZTJHDEXGCKAXRZ-FNORWQNLSA-N

物化性质

• 沸点：
  72-73 °C(Press: 134 Torr)
• 密度：
  0.755 g/cm3
• 保留指数：
  788

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  8
• 可旋转键数：
  4
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.25
• 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：

  (E)-1,3,7-octatriene 在 palladium on activated charcoal 、 Ps(acac)2 、 三乙基铝 、 三苯基膦 氢气 作用下， 以 乙酸乙酯 、 甲苯 为溶剂， 反应 6.0h， 生成 1-nonylpiperidine
  参考文献：
  名称：

  Catalytic synthesis of unsaturated tertiary amines

  摘要：

  DOI：

  10.1007/bf00961758
• 作为产物：
  描述：

  1,3-丁二烯 在 palladium diacetate 三苯基膦 作用下， 以 乙腈 为溶剂， 生成 (E)-1,3,7-octatriene
  参考文献：
  名称：

  Influence of the acidity of the hydrogen undergoing β-elimination on the outcome of oligomerization and co-oligomerization processes of functionalized conjugated dienes in presence of palladium catalysts.

  摘要：

  DOI：

  10.1016/s0040-4039(00)89193-5

文献信息

• Hydroformylation of 1,6-dienes with carbonylhydridotris(triphenylphosphine)rhodium
  作者：Ronald Grigg、Gerald J. Reimer、Alan R. Wade

  DOI：10.1039/p19830001929

  日期：——

  using [Rh(H)CO(PPh3)3] as catalyst. Octa-1,6-dienes are hydroformylated specifically at the terminal double bond and good selectivity for the n-aldehyde is observed when a 2:1 mixture of hydrogen and carbon monoxide are used. Both mono- and di-formyl derivatives are formed from 4,4-diacetylhepta-1,6-diene, with a strong preference for n-aldehydes. The effect of catalyst concentration on product distribution

  使用[Rh（H）CO（PPh 3）3在室温和大气压下已实现了许多1,6-二烯的加氢甲酰化]作为催化剂。Octa-1,6-二烯专门在末端双键处被加氢甲酰化，当使用氢气和一氧化碳的2：1混合物时，可观察到对正醛的良好选择性。单-和二-甲酰基衍生物均由4,4-二乙酰基庚-1,6-二烯形成，强烈推荐使用正醛。报告了催化剂浓度对产物分布的影响。通过用一氧化硫或二氧化硫保护二烯部分作为其环加合物，可以选择性地将Octa-1,3,7-三烯加氢甲酰化，并且在亚甲基环戊烷进行区域特异性加氢甲酰化的同时，亚甲基环丁烷异构化为甲基环丁烯。
• Diastereoselective Three-Component 3,4-Amino Oxygenation of 1,3-Dienes Catalyzed by a Cationic Heptamethylindenyl Rhodium(III) Complex
  作者：Finn Burg、Tomislav Rovis

  DOI：10.1021/jacs.1c09276

  日期：2021.11.3

  tool to rapidly access β-amino alcohols–a privileged motif ubiquitous in natural products, pharmaceuticals and agrochemicals. Although a variety of expedient methods are established for simple alkenes, selective amino oxygenation of 1,3-dienes is less explored. Within this context, methods for the oxyamination of 1,3-dienes that are selective for the internal position remain unprecedented. We herein report

  烯烃的直接氧胺化是快速获得 β-氨基醇的有力工具，β-氨基醇是天然产物、药物和农用化学品中普遍存在的一种特殊基序。尽管针对简单烯烃建立了多种权宜之计，但对 1,3-二烯烃的选择性氨基氧化作用的探索较少。在这种情况下，对内部位置具有选择性的 1,3-二烯的氧胺化方法仍然是前所未有的。我们在此报告了一种模块化的三组分方法来执行由阳离子七甲基茚基 (Ind*) Rh(III) 配合物催化的 1,3-二烯的内部和高度非对映选择性氨基氧化。
• The telomerisation of 1,3-butadiene and carbon dioxide: process development and optimisation in a continuous miniplant
  作者：Arno Behr、Marc Becker

  DOI：10.1039/b608552k

  日期：——

  The telomerisation of 1,3-butadiene and carbon dioxide is one of the first homogeneously catalyzed reactions using carbon dioxide as a C1-building block. In this article we describe the process development for a miniplant applying this telomerisation in a continuous scale. Through repeated optimisation of the plant setup combined with parallel laboratory batch experiments the overall space-time-yield of the plant was enhanced significantly.

  1,3-丁二烯和二氧化碳的端聚反应是最早利用二氧化碳作为C1构建单元进行均相催化反应之一。 本文中， 我们描述了在小规模的工厂中应用这一端聚反应进行连续生产的过程开发。通过对工厂设备多次优化以结合平行的实验室批次实验， 工厂的整体空间时间产率得到显著提升。
• Mechanistic Studies on Pd-Catalyzed Telomerization and Co-Cyclization of Butadiene: Amphiphilicity of Bis-π-allylpalladium Intermediate in the Presence of Phosphine Ligand
  作者：Jitsuo Kiji、Tamon Okano、Takaaki Nomura、Kayoko Saiki、Torei Sai、Jiro Tsuji

  DOI：10.1246/bcsj.74.1939

  日期：2001.10

  Pd-catalyzed reactions of butadiene, which proceed through a bis-π-allylpalladium intermediate, (η3,η3-C8H12)Pd (2), were performed in the presence of both a pronucleophile (aceto- or cyanoacetate) and an electrophile (benzaldehyde). Methyl aceto- or cyanoacetate and benzaldehyde reacted independently with 2 to give telomers 8 and the divinyl-substituted pyranes 9, respectively. In the case of methyl cyanoacetate, the co-cyclization of 2 with 2-cyano-3-phenylpropenoate (11) formed in situ also took place to afford the cyclohexane derivative 10. Namely, three kinds of amphiphilic additions of the C8-chain of 2 occurred to δ+H–Nuδ−, δ+C=Cδ−, and δ+C=Oδ− simultaneously in a one-pot reaction. The Pd-catalyzed reaction of allyl chloride, allyltributylstannane, methyl cyanoacetate, and benzaldehyde was undertaken under neutral conditions, expecting the amphiphilic reactions by the intermediacy of (η3-C3H5)2Pd (6) formed in situ. Allylation of both benzaldehyde and methyl cyanoacetate took place. Competitively amphiphilic bis-allylation of the polar double bond of 11 also occurred to form the 1,7-octadiene derivative 18. The mechanisms of both reactions can be explainable in terms of the amphiphilicity of the intermediates (2 and 6) in the presence of a phosphine ligand.

  在乙酸或氰乙酸作为亲核试剂和苯甲醛作为亲电试剂的存在下，通过双π-烯丙基金属中间体（η3,η3-C8H12）Pd（2）进行的钯催化丁二烯反应分别生成了8聚体和二乙烯基取代的吡喃9。对于氰乙酸甲酯的情况下，由2与现场生成的2-氰基-3-苯基丙烯酸酯（11）进行的共环化反应也同时发生，形成了环己烷衍生物10。也就是说，在单锅反应中，同时发生了C8链的2对δ+H–Nuδ−、δ+C=Cδ−和δ+C=Oδ−亲油性加成的三种类型反应。在无碱性条件下，利用现场生成的（η3-C3H5）2Pd（6）作为中间体，进行了三氯甲硅烷丙烯、三丁基锡丙烯、氰乙酸甲酯和苯甲醛的钯催化反应。苯甲醛和氰乙酸甲酯都发生了丙烯基化反应。极性双键11也通过竞争性的亲油性双丙烯基化反应形成了1,7-辛二烯衍生物18。这两种反应的机理都可以在存在磷配体的情况下，根据中间体（2和6）的亲油性进行解释。
• Telomerization of Butadiene withL-Arabinose andD-Xylose in DMF: Selective Formation of their Monooctadienyl Glycosides
  作者：Boris Estrine、Sandrine Bouquillon、Françoise Hénin、Jacques Muzart

  DOI：10.1002/ejoc.200400064

  日期：2004.7

  Conditions to achieve the palladium-catalysed telomerization of butadiene with L-arabinose and D-xylose as telogens have been identified. With DMF as solvent, optimised ratios of substrate, reactants and catalytic system allowed the selective grafting of one octadienyl chain onto the anomeric hydroxy group. (© Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2004)

  已经确定了用 L-阿拉伯糖和 D-木糖作为调聚剂实现钯催化的丁二烯调聚的条件。以 DMF 作为溶剂，优化的底物、反应物和催化体系的比例允许一个辛二烯链选择性接枝到异头羟基上。(© Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2004)