7-butyl-5-methylenetridecane | 122833-07-2

• 分子结构分类: 有机化合物 - 碳氢化合物 - 不饱和烃
• 英文名称: 7-butyl-5-methylenetridecane
• 英文别名: 2,4-Dibutyl-1-decene；7-butyl-5-methylidenetridecane
• CAS: 122833-07-2
• 化学式: C₁₈H₃₆
• 分子量: 252.484
• InChiKey: CUTCIBVXOXUSGT-UHFFFAOYSA-N

物化性质

• 沸点：
  316.0±9.0 °C(Predicted)
• 密度：
  0.786±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  9.1
• 重原子数：
  18
• 可旋转键数：
  13
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.89
• 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：

  7-butyl-5-methylenetridecane 在 palladium on activated charcoal 、 氢气 作用下， 生成 7-butyl-5-methyltridecane
  参考文献：
  名称：

  1-Hexene: a renewable C6 platform for full-performance jet and diesel fuels

  摘要：

  我们开发出了一种将 1-己烯转化为喷气燃料和柴油燃料的高效选择性工艺。结合乙醇脱水和乙烯三聚的商业工艺，这项工作为利用生物乙醇合成高性能碳氢化合物燃料奠定了基础。在常温常压下，使用 Cp2ZrCl2/MAO 催化剂对 1-hexene 进行选择性低聚，可将 1-hexene 100%转化为二聚体和三聚体的混合物，选择性大于 80%。氢化二聚体的 -20 °C 粘度仅为 3.5 mPa s，凝固点特别低，为 -77 °C ，十六烷值为 67，这表明它具有适用于喷气燃料和柴油燃料的性能特点。氢化三聚体的闪点为 128 °C，十六烷值为 92，40 °C 粘度为 3.1 mPa s，-20 °C 粘度为 24.5 mPa s。除了燃料范围内的碳氢化合物外，较重的低聚物还有可能用作生物润滑剂，从而将有用产品的碳产量提高到接近定量水平。

  DOI：

  10.1039/c3gc41554f
• 作为产物：
  描述：

  1-己烯 生成 7-butyl-5-methylenetridecane
  参考文献：
  名称：

  KAMINSKY, WALTER;MOLLER-LINDENHOF, NICO;AHLERS, AURELIA

  摘要：

  DOI：

文献信息

• Diastereoselective synthesis of functionally substituted alkene dimers and oligomers, catalysed by chiral zirconocenes
  作者：Pavel V. Kovyazin、Il'giz N. Abdullin、Lyudmila V. Parfenova

  DOI：10.1016/j.catcom.2018.10.032

  日期：2019.1

  The research addresses the reaction of terminal alkenes and propene with AlR3 (R = Me, Et) in the presence of chiral Zr complexes, rac-[Y(η5-C9H10)2]ZrCl2 (Y = C2H4, SiMe2) or (NMI)2ZrCl2 (NMI- η5–neomenthylindenyl), and methylaluminoxane. The effect of reaction conditions, catalyst and trialkylalane structure on the substrate conversion and the reaction chemo- and stereoselectivity has been studied

  研究地址末端烯烃的反应和丙烯与为AlR 3中的手性锆复合物，的存在下（R =甲基，乙基）外消旋- [Y（η 5 -C 9 ħ 10）2 ]的ZrCl 2（Y = C 2 ħ 4，森达2）或（NMI）2的ZrCl 2（NMI- η 5–neomenthylindenyl）和甲基铝氧烷。研究了反应条件，催化剂和三烷基铝烷结构对底物转化率以及反应化学和立体选择性的影响。该反应主要经历烯烃甲基（乙基）锆化的阶段，随后将底物分子引入Zr-C键中。结果，开发了用于合成官能取代的线性末端烯烃二聚体和丙烯低聚物的非对映选择性一锅法。
• Structurally uniform 1-hexene, 1-octene, and 1-decene oligomers: Zirconocene/MAO-catalyzed preparation, characterization, and prospects of their use as low-viscosity low-temperature oil base stocks
  作者：Ilya E. Nifant’ev、Alexander A. Vinogradov、Alexey A. Vinogradov、Igor V. Sedov、Viktor G. Dorokhov、Anton S. Lyadov、Pavel V. Ivchenko

  DOI：10.1016/j.apcata.2017.09.016

  日期：2018.1

  alkanes, and higher oligomers. Trimers, tetramers, and pentamers of 1-hexene, 1-octene, and 1-decene were isolated as individual compounds and were hydrogenated. Viscosity characteristics of the isolated saturated and unsaturated hydrocarbons have been studied at various temperatures. The isolated saturated oligomers of 1-octene and 1-decene outperform the traditional electrophilic oligomerization

  已经阐述了用于这种反应的原始的α-烯烃低聚方法以及新型的热稳定的锆茂催化剂。报告的方法可以实现轻质α-烯烃低聚物的馏分，产率高达90％，而不会大量形成副产物，如内部烯烃，烷烃和高级低聚物。分离出1-己烯，1-辛烯和1-癸烯的三聚体，四聚体和五聚体作为单独的化合物并进行氢化。已经在各种温度下研究了分离的饱和和不饱和烃的粘度特性。分离的1-辛烯和1-癸烯饱和低聚物在粘度指数，倾点和低温粘度方面优于传统的亲电子低聚产物。
• Efficient 1-Hexene Trimerization with Triazacyclohexane Chromium Catalysts and Detailed Product Analysis by ¹³C NMR
  作者：Alexander G. N. Coxon、Randolf D. Köhn

  DOI：10.1021/acscatal.6b00542

  日期：2016.5.6

  1-hexene, and 1-octene with unprecedented activity, reaching nearly 5000 turnovers in 1 h. The isomer distribution of the trimers has been analyzed in detail by application of quantitative 13C NMR spectroscopy to 13C labeled samples. All endocyclic elimination products predicted by the metallacyclic mechanism have been characterized, and many have been confirmed by their independent syntheses. Significant

  描述了三氮杂环己烷铬预催化剂，该催化剂以前所未有的活性催化1-戊烯，1-己烯和1-辛烯的选择性三聚，在1小时内达到了近5000次营业额。三聚体的异构体分布已通过将13 C NMR定量光谱应用于13C标记的样品。已经表征了通过金属环机理预测的所有环内消除产物，并且许多产物已经通过其独立的合成得到了证实。在配体体积变化时观察到异构体分布的显着变化。定量分析对金属环中间体的相对丰度给出了可观的见解，其中1,3-取代的色环戊烷是迄今为止最丰富的静止状态。环的扩展选择性有利于1,2-插入受阻较少的Cr-C键，但是也发现了一些2,1-插入的产物。
• Catalytic oligomerization of α-olefins in the presence of two-stage activated zirconocene catalyst based on 6,6-dimethylfulvene ‘dimer’
  作者：Ilya E. Nifant’ev、Alexey A. Vinogradov、Alexander A. Vinogradov、Stanislav I. Bezzubov、Pavel V. Ivchenko

  DOI：10.1016/j.mencom.2017.01.010

  日期：2017.1

  Zirconocene obtained from 6,6-dimethylfulvene 'dimer', being activated subsequently with triisobutylaluminium and methylalumoxane, catalyzes transformation of alpha-olefins into a mixture of vinylidene oligomers with minimal losses to isomerization, which allows one to consider this catalyst perspective for the synthesis of branched hydrocarbons with uniform structure.
• Highly Efficient and 1,2-Regioselective Method for the Oligomerization of 1-Hexene Promoted by Zirconium Precatalysts with [OSSO]-Type Bis(phenolate) Ligands
  作者：Norio Nakata、Kazuaki Nakamura、Akihiko Ishii

  DOI：10.1021/acs.organomet.8b00411

  日期：2018.8.13

  A mixture of zirconium complex 7, which carries a phenyl-substituted [OSSO]-type bis(phenolate) ligand, and dried modified methylaluminoxane (dMMAO) catalyzes the 1,2-regioselective oligomerization of 1-hexene at relatively low catalyst loadings (0.0056 mol %) to produce the corresponding vinylidene-terminated dimer, 5-methyleneundecane (74-80%), and trimer, 7-butyl-5-methylenetridecane (8-11%). The observed turnover frequencies (TOFs) are relatively high (up to 11 100 h(-1)). When a mixture of 2,6-dimethylphenyl-substituted precatalyst 8 and dMMAO was used, the oligomerization of 1-hexene proceeded effectively to afford predominantly the dimer (87-91%) together with a small amount of the trimer (8-11%) at remarkably high TOFs (up to 6640 h(-1)).