1,4-二(异丙基)萘 | 24157-79-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 中文名称: 1,4-二(异丙基)萘
• 中文别名: 4-甲基-2-(三氟甲磺酰)氧代吡啶
• 英文名称: 1,4-diisopropylnaphthalene
• 英文别名: 1,4-DIPN；1,4-diisopropyl-naphthalene；1,4-Diisopropyl-naphthalin；1,4-bis(isopropyl)naphthalene；1.4-Diisopropyl-naphthalin；1,4-Diisopropylnaphthalin；1,4-di(propan-2-yl)naphthalene
• CAS: 24157-79-7
• 化学式: C₁₆H₂₀
• 分子量: 212.335
• InChiKey: BDJUQNIAPKYGNU-UHFFFAOYSA-N

物化性质

• 保留指数：
  1709

计算性质

• 辛醇/水分配系数(LogP)：
  5.9
• 重原子数：
  16
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  0
• 氢给体数：
  0
• 氢受体数：
  0

安全信息

• 海关编码：
  2902909090
• 储存条件：
  2-8°C

反应信息

• 作为反应物：
  描述：

  1,4-二(异丙基)萘 在 硝酸 作用下， 生成 1,4-萘二甲酸
  参考文献：
  名称：

  Hueckel,W.; Cramer,R., Justus Liebigs Annalen der Chemie, 1960, vol. 630, p. 89 - 104

  摘要：

  DOI：
• 作为产物：
  描述：

  Δ²-Dihydro-1,4-diisopropyl-naphthalin 在 对苯醌 作用下， 以 1,4-二氧六环 为溶剂， 生成 1,4-二(异丙基)萘
  参考文献：
  名称：

  Hueckel,W.; Cramer,R., Justus Liebigs Annalen der Chemie, 1960, vol. 630, p. 89 - 104

  摘要：

  DOI：

文献信息

• C–C Bond-Forming and Bond-Breaking Processes from the Reaction of Diesters with Me₃SnLi. Synthesis of Complex Bridged Polycycles and Dialkyl Aromatic Compounds
  作者：Lucas Martínez-García、Rubén Lobato、Gustavo Prado、Pablo Monje、F. Javier Sardina、M. Rita Paleo

  DOI：10.1021/acs.joc.8b02891

  日期：2019.2.15

  followed by a reaction of the resulting unsaturated diesters with Me3SnLi. We propose that a stanna-Brook rearrangement plays a fundamental role in the formation of the polycyclic organotin acetals obtained. These unusual compounds could be further functionalized by tin–lithium exchange followed by alkylation of the newly formed tertiary carbanion. Alternatively, dialkylated aromatic hydrocarbons have

  1,2-芳族二酯可以通过两步程序转变为应变桥联多环结构，该程序包括由碱金属促进的初始还原烷基化，然后使所得的不饱和二酯与Me 3 SnLi反应。我们提出，斯坦纳-布鲁克重排在获得的多环有机锡缩醛的形成中起基本作用。这些不寻常的化合物可以通过锡-锂交换，然后对新形成的叔碳负离子进行烷基化来进一步功能化。或者，已经通过Me 3 SnLi促进的脱碳反应制备了二烷基化的芳族烃。1,4-芳族二酯经过还原二烷基化，然后通过与Me 3反应转化为降冰片二烯酮衍生物SnLi。从蒽38开始，仅用两步就制备了几种稳定的二苯并降冰片二烯酮41。相应的萘类似物得到1,4-二烷基萘。所描述的合成协议提供对通过现有合成方法不容易获得的结构的访问。
• Regioselective Arene Functionalization: Simple Substitution of Carboxylate by Alkyl Groups
  作者：Tobias Krüger、Katja Vorndran、Torsten Linker

  DOI：10.1002/chem.200901774

  日期：2009.11.9

  from toluic and naphthoic acids, the carboxylate group was conveniently substituted by alkyl halides by Birch reduction and subsequent decarbonylation. The method is characterized by inexpensive starting materials and reagents, and methylation of arenes was realized. Besides simple alkyl substituents, the scope of arene functionalization was extended by benzyl, fluoro, amino, and ester groups. We were

  具有各种烷基侧链的芳烃以高收率和优异的区域选择性合成。从甲苯甲酸和萘甲酸开始，通过桦木还原和随后的脱羰作用，羧酸根基团可以方便地被烷基卤取代。该方法的特点是原料和试剂便宜，实现了芳烃的甲基化。除了简单的烷基取代基以外，芳烃官能化的范围还扩大了苄基，氟，氨基和酯基。通过添加叔丁醇，我们能够在桦木还原过程中控制1-萘甲酸的烷基化。这样就可以从相同的原料进行区域选择性合成单和双取代的萘。
• Isopropylation of naphthalene by isopropanol over conventional and Zn- and Fe-modified USY zeolites
  作者：Marimuthu Banu、Young Hye Lee、Ganesan Magesh、Jae Sung Lee

  DOI：10.1039/c3cy00691c

  日期：——

  Catalytic performances of USY, MOR, and BEA zeolites were compared for the isopropylation of naphthalene by isopropyl alcohol in a high-pressure, fixed-bed reactor. The USY catalyst showed a high conversion of 86% and good stability but a low 2,6-/2,7-DIPN shape selectivity ratio of 0.94. In contrast, over the MOR catalyst, 2,6-DIPN was selectively synthesized with a high 2,6-/2,7-DIPN ratio of 1.75, but low naphthalene conversions and fast deactivation of the catalyst were observed. The USY catalyst was modified by Zn and Fe using the wet impregnation method to enhance the selectivity for 2,6-DIPN. The highest conversion (~95%) and selectivity for 2,6-DIPN (~20%) were achieved with 4% Zn/USY catalyst. It appeared that small metal oxide islands formed in the USY pores to decrease the effective pore size and thus render it mildly shape-selective. Zn loading also decreased the number of strong acid sites responsible for coke formation and increased the number of weak acid sites. The high conversion and stability of Zn-modified catalysts were ascribed to the presence of a suitable admixture of weak and strong acid sites with less coke deposition. The Fe-modified USY catalysts were less effective because the modification increased the number of the strong acid sites.

  比较了 USY、MOR 和 BEA 沸石在高压固定床反应器中用异丙醇对萘进行异丙基化反应的催化性能。USY 催化剂的转化率高达 86%，稳定性良好，但 2,6-/2,7-二硝基萘的形状选择性较低，仅为 0.94。相反，在 MOR 催化剂上，2,6-DIPN 被选择性合成，2,6-/2,7-DIPN 比率高达 1.75，但萘转化率低，催化剂失活快。采用湿浸渍法对 USY 催化剂进行了锌和铁改性，以提高 2,6-DIPN 的选择性。在使用 4% Zn/USY 催化剂时，2,6-DIPN 的转化率（约 95%）和选择性（约 20%）最高。USY 孔中似乎形成了小的金属氧化物岛，从而减小了有效孔径，使其具有轻微的形状选择性。此外，锌的添加还减少了导致焦炭形成的强酸位点的数量，增加了弱酸位点的数量。Zn 改性催化剂的高转化率和稳定性可归因于弱酸和强酸位点的适当混合以及较少的焦炭沉积。铁改性 USY 催化剂的效果较差，因为改性增加了强酸位点的数量。
• The Alkylation of Naphthalene over One-Dimensional Fourteen-Membered Ring Zeolites. The Influence of Zeolite Structure and Alkylating Agent on the Selectivity for Dialkylnaphthalenes
  作者：Yoshihiro Sugi、Hiroyoshi Maekawa、Hiroaki Naiki、Kenichi Komura、Yoshihiro Kubota

  DOI：10.1246/bcsj.81.1166

  日期：2008.9.15

  The alkylation, i.e., isopropylation, s-butylation, and t-butylation, of naphthalene (NP) was examined over one-dimensional fourteen-membered (14-MR) zeolites: CIT-5 (CFI), UTD-1 (DON), and SSZ-53 (SFH), and compared to the results over H-mordenite (MOR) to elucidate how zeolite structure and alkylating agent play roles in the shape-selective catalysis. The β,β-selectivities (for β,β-dialkylnaphthalene (2,6- and 2,7-dialkylnaphthalenes, β,β-DAN)) and the 2,6-selectivities (for 2,6-DAN) were varied with the types of zeolite and of alkylating agent. MOR gave high β,β-selectivities in the all alkylations in the range of 150–300 °C. However, the 14-MR zeolites, CFI, DON, and SFH, gave much lower β,β-selectivities in the isopropylation: bulky and less stable α,β- and α,α-diisopropylnaphthalenes (α,β-DIPN: 1,3-, 1,5-, and 1,7-DIPN); α,α-DIPN (1,4- and 1,5-DIPN) were predominantly obtained under kinetic control at low temperatures, and stable and less bulky β,β-DIPN were formed under thermodynamic control at high temperatures. The β,β-selectivities were higher than 95% over CFI in the s-butylation, and increased from 50–60% at 150 °C to 75% at 300 °C over DON and SFH, respectively. They were almost 100% in the t-butylation over all zeolites. The alkylation over MOR occurred with high 2,6-selectivities in the range of 150–250 °C: 60% for the isopropylation, 80% for the s-butylation, and 95% for the t-butylation. CFI, DON, and SFH gave the 2,6-selectivities in the range of 5–30% in the isopropylation, 65%, 55%, and 50%, respectively, in the s-butylation, and higher than 80% in the t-butylation. These different features are explained by the discrimination of the least bulky DAN isomers from the other isomers by steric restriction with the zeolite channels at the transition states: β,β-DAN from the DAN isomers, and 2,6-DAN from β,β-DAN. The bulkiness of alkylating agent also enhances the discrimination of the isomers, particularly, between 2,6- and 2,7-DAN. The β,β- and 2,6-selectivities are synergistically governed by the zeolite channel and the bulkiness of alkylating agents.

  研究了萘 (NP) 在一维十四元胞（14-MR）沸石上的烷基化，即异丙基化、叔丁基化和叔丁基化：CIT-5（CFI）、UTD-1（DON）和 SSZ-53（SFH），并与 H-莫来石（MOR）上的结果进行了比较，以阐明沸石结构和烷基化剂如何在形状选择催化中发挥作用。β,β-选择性（对 β,β-二烷基萘（2,6- 和 2,7-二烷基萘，β,β-DAN））和 2,6-选择性（对 2,6-DAN）随沸石类型和烷化剂的不同而变化。在 150-300 °C 范围内，MOR 在所有烷基化反应中都具有较高的β,β-选择性。然而，14-MR 沸石、CFI、DON 和 SFH 在异丙基化反应中的 β、β-选择性要低得多：体积大且不太稳定的 α、β- 和 α、α-二异丙基萘（α、β-DIPN：α,β-二异丙基萘（α,β-DIPN：1,3-、1,5- 和 1,7-DIPN）；α,α-二异丙基萘（1,4- 和 1,5-DIPN）主要是在低温下通过动力学控制获得的，而稳定且体积较小的 β,β-二异丙基萘则是在高温下通过热力学控制形成的。在 s 丁基化反应中，相对于 CFI 的 β,β-选择性高于 95%，相对于 DON 和 SFH 的 β,β-选择性分别从 150 ℃ 时的 50-60% 增加到 300 ℃ 时的 75%。在所有沸石上的 t-丁基化过程中，烷基化率几乎达到 100%。在 150-250 °C的范围内，在 MOR 上发生的烷基化具有很高的 2,6-选择性：异丙基化为 60%，s-丁基化为 80%，t-丁基化为 95%。CFI、DON 和 SFH 在异丙基化反应中的 2,6 选择性为 5-30%，在 s-丁基化反应中分别为 65%、55% 和 50%，而在 t-丁基化反应中则高于 80%。这些不同特征的原因是，在过渡状态下，沸石通道的立体限制将体积最小的 DAN 异构体与其他异构体区分开来：β,β-DAN 与 DAN 异构体区分开来，2,6-DAN 与 β,β-DAN 区分开来。烷基化剂的体积也提高了异构体的鉴别能力，特别是 2,6- 和 2,7-DAN 之间的鉴别能力。沸石通道和烷基化剂的体积对 β、β- 和 2,6-选择性具有协同作用。
• Zeolite Pore Entrance Effect on Shape Selectivity in Naphthalene Isopropylation
  作者：R Brzozowski

  DOI：10.1006/jcat.2002.3702

  日期：2002.9.10

  obtained over zeolites than over amorphous aluminosilicate catalysts. The explanation of such results was proposed to be a specific shape-selectivity effect of alkylation reaction occurring in the entrances to the pores of zeolite. This type of shape selectivity can be very significant and conceal other shape-selectivity effects such as β-selectivity of reactions occurring inside the pores. Results available

  在各种大孔沸石以及无定形硅铝酸盐催化剂上研究了丙烯与丙烯的萘烷基化。在不同温度下比较了异丙基萘和二异丙基萘的异构分布。令人惊讶地，在沸石上获得的产物比在无定形铝硅酸盐催化剂上观察到的产物中观察到更高的单烷基化α-选择性和更高的二异丙基化中的大体积异构体浓度。提出这种结果的解释是在沸石孔的入口处发生的烷基化反应的特定形状选择性作用。这种类型的形状选择性可能非常显着，并掩盖了其他形状选择性效果，例如在孔内发生的反应的β选择性。从文献中得出的结果，