1,3,5-三辛基苯 | 7694-77-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 中文名称: 1,3,5-三辛基苯
• 英文名称: 1,3,5-trioctylbenzene
• 英文别名: Benzene, 1,3,5-trioctyl-
• CAS: 7694-77-1
• 化学式: C₃₀H₅₄
• 分子量: 414.759
• InChiKey: POAUVINXPNKFII-UHFFFAOYSA-N

物化性质

• 沸点：
  239-240 °C(Press: 2 Torr)
• 密度：
  0.8525 g/cm3

计算性质

• 辛醇/水分配系数(LogP)：
  14.1
• 重原子数：
  30
• 可旋转键数：
  21
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.8
• 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：

  1,3,5-三辛基苯 在 N-碘代丁二酰亚胺 、 三氟甲磺酸 作用下， 以 1,2-二氯乙烷 为溶剂， 反应 3.0h， 以70%的产率得到1,3,5-Triiodo-2,4,6-trioctylbenzene
  参考文献：
  名称：

  1,3,5-Trialkyl-2,4,6-triiodobenzenes:  Novel X-ray Contrast Agents for Gastrointestinal Imaging

  摘要：

  Examination of the gastrointestinal (GI) tract has been performed for decades using barium sulfate. Although this agent has many recognized limitations including extreme radiopacity, poor intrinsic affinity for the GI mucosa, and very high density, no alternative contrast agents have emerged which produce comparable or better contrast visualization. In fact, the various techniques of the GI radiologic examination (i.e., single contrast, double contrast, biphasic) were developed to compensate for its limitations. Each of these techniques requires complex patient manipulation to achieve adequate mucosal coating or compression to overcome the marked radiopacity of barium sulfate in order to obtain a diagnostically useful examination. A Series of novel radiopaque oils, the 1,3,5-trialkyl-2,4,6-triiodobenzenes, was designed to improve the efficacy, stability, and safety of barium formulations. These substances were prepared in two steps from 1,3,5-trichlorobenzene. Compound 17 (1,3,5-tri-n-hexyl-2,4,6-triiodobenzene) formulated as an oil-in-water emulsion, was found to be well-tolerated in rodents (mice, hamsters, rats) following acute oral and/or intraperitoneal administrations at 4 times the anticipated human clinical dose. No metabolism of 17 was detected in rat, hamster, dog, monkey, or human hepatic microsomes, suggesting the lack of oral toxicity was a consequence of poor absorption.

  DOI：

  10.1021/jm990407i
• 作为产物：
  描述：

  1-癸炔 在 Al(iBu)3*TiCl4 作用下， 以 异辛烷 为溶剂， 生成 1,3,5-三辛基苯
  参考文献：
  名称：

  Makovetskii,K.L. et al., Journal of Organic Chemistry USSR (English Translation), 1966, vol. 2, p. 757 - 761

  摘要：

  DOI：

文献信息

• Synthesis, characterization and catalytic application of some novel PNP-Ni(II) complexes: Regio-selective [2+2+2] cycloaddition reaction of alkyne
  作者：Masilamani Tamizmani、Chinnappan Sivasankar

  DOI：10.1016/j.jorganchem.2017.02.039

  日期：2017.9

  We have also performed alkyne [2+2+2] cycloaddition reaction using Ni(II) complexes and observed high regioselectivity of the products. The observed selectivity is well correlating with the electronic feature of alkynes. The [2+2+2] cycloaddition of electron rich alkynes produced 1,3,5-substituted benzene derivatives as a major product whereas the electron deficient alkynes produced 1,2,4-substituted

  PN（H）P Ph，PN（Me）P iPr和PN（Me）P tBu配体的一些新颖的Ni（II）配合物已通过标准的分析和光谱方法（例如1 H NMR，31 P NMR，元素分析，ESI-MS，紫外可见光谱和单晶X射线晶体学。在三氟甲磺酸银存在下，复合物[PN（H）P Ph NiCl] 2 NiBr 4 （5）在室温下激活二氯甲烷的C-Cl键，得到复合物[PN（H）P Ph NiCl] OTf （6）。我们还使用Ni（II）配合物进行了炔烃[2 + 2 + 2]环加成反应，并观察到了产物的高区域选择性。观察到的选择性与炔烃的电子特征很好地相关。富电子炔烃的[2 + 2 + 2]环加成反应生成1,3,5-取代的苯衍生物作为主要产物，而缺电子炔烃则生成1,2,4-取代的苯衍生物作为主要产物。
• Production of renewable lubricants via self-condensation of methyl ketones
  作者：Madhesan Balakrishnan、George E. Arab、Omar B. Kunbargi、Amit A. Gokhale、Adam M. Grippo、F. Dean Toste、Alexis T. Bell

  DOI：10.1039/c6gc00579a

  日期：——

  Self-condensation of biomass-derived methyl ketones catalyzed by solid bases or acids produces corresponding cyclic trimers exclusively in excellent yields. Hydrogenated versions of such trimers can be good lubricants.

  固体碱或酸催化的生物质衍生的甲基酮的自缩合可产生相应的环状三聚体，且产率极高。这种三聚体的氢化形式可以是良好的润滑剂。
• Short synthesis of methylenecyclopentenones by intermolecular Pauson–Khand reaction of allyl thiourea
  作者：Željko Petrovski、Bruno M.R. Martins、Carlos A.M. Afonso

  DOI：10.1016/j.tetlet.2010.04.025

  日期：2010.6

  N,N,N′-Trimethylallylthiourea promotes the intermolecular Pauson–Khand reaction with alkynes in the presence of Co2(CO)8 and moderate pressure of CO followed by thiourea elimination allowing the formation of methylenecyclopentenone derivatives.

  N，N，N'-三甲基烯丙基硫脲在存在Co 2（CO）8和中等压力的CO的情况下促进与炔烃的分子间Pauson-Khand反应，然后通过硫脲消除而形成亚甲基环戊烯酮衍生物。
• Silica-Supported Tungsten Carbynes (≡SiO)_<i>x</i>W(≡CH)(Me)_<i>y</i> (<i>x</i> = 1, <i>y</i> = 2; <i>x</i> = 2, <i>y</i> = 1): New Efficient Catalysts for Alkyne Cyclotrimerization
  作者：Nassima Riache、Alexandre Dery、Emmanuel Callens、Albert Poater、Manoja Samantaray、Raju Dey、Jinhua Hong、Kun Li、Luigi Cavallo、Jean-Marie Basset

  DOI：10.1021/om500684e

  日期：2015.2.23

  carbyne complexes (≡SiO)xW(≡CH)(Me)y (x = 1, y = 2; x = 2, y = 1) toward alkynes is reported. We found that they are efficient precatalysts for terminal alkyne cyclotrimerization with high TONs. We also demonstrate that this catalyst species is active for alkyne cyclotrimerization without the formation of significant alkyne metathesis products. Additional DFT calculations highlight the importance of the

  据报道，二氧化硅负载的钨碳炔复合物（≡SiO）x W（≡CH）（Me）y（x = 1，y = 2; x = 2，y = 1）对炔烃的活性。我们发现它们是高TON的末端炔烃环三聚的有效预催化剂。我们还证明了该催化剂种类对于炔烃环三聚反应是有效的，而不会形成明显的炔烃复分解产物。额外的DFT计算强调了W协调领域在支持这种实验行为方面的重要性。
• Synthesis of 1,3,5-trialkylbenzenes from anils of methyl alkyl ketones
  作者：Robert W. Layer

  DOI：10.1021/jo00335a046

  日期：1981.10