2-(2-hydroperoxy-2-methylethyl)-6-(2-methylethyl)naphthalene | 105443-43-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 2-(2-hydroperoxy-2-methylethyl)-6-(2-methylethyl)naphthalene
• 英文别名: 2-isopropyl-6-(1-hydroperoxy-1-methylethyl)naphthalene；2-(1-hydroperoxy-1-methylethyl)-6-(1-methylethyl)naphthalene；2-(2-hydroperoxy-2-propyl)-6-isopropylnaphthalene；Hydroperoxide, 1-methyl-1-[6-(1-methylethyl)-2-naphthalenyl]ethyl；2-(2-hydroperoxypropan-2-yl)-6-propan-2-ylnaphthalene
• CAS: 105443-43-4
• 化学式: C₁₆H₂₀O₂
• 分子量: 244.334
• InChiKey: CDVVHSFGSFPECK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4
• 重原子数：
  18
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  29.5
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  2-(2-hydroperoxy-2-methylethyl)-6-(2-methylethyl)naphthalene 在 硫酸 作用下， 以 乙腈 为溶剂， 反应 2.0h， 生成 6-isopropyl-2-naphthol
  参考文献：
  名称：

  N-羟基邻苯二甲酰亚胺（NHPI）/α，α'-偶氮二异丁腈（AIBN）催化二异丙基萘的需氧氧化合成萘二醇

  摘要：

  一锅反应成功地合成了萘二醇，方法是将N-羟基邻苯二甲酰亚胺（NHPI）与α，α'-偶氮二异丁腈（AIBN）结合催化空气氧化二异丙基萘，然后用硫酸分解。因此，在A3N（3 mol％）和NHPI（10 mol％）存在下于75°C的CH 3 CN中用空气（20 atm）氧化2,6-二异丙基萘21小时，然后用0.3 MH处理2 SO 4以92％的收率得到2，6-萘二醇。

  DOI：

  10.1002/adsc.200303168
• 作为产物：
  描述：

  2,6-二异丙基萘 在 氧气 、 1,1'-偶氮(氰基环己烷) 作用下， 反应 6.0h， 以11.4%的产率得到2-(2-hydroperoxy-2-methylethyl)-6-(2-methylethyl)naphthalene
  参考文献：
  名称：

  Oxidation of 2-methoxy-6-(1-methylethyl)naphthalene with oxygen

  摘要：

  Aerobic oxidation of 2-methoxy-6-(1-methylethyl)naphthalene to hydroperoxide, alcohol, and ketone, is reported. These compounds, particularly 2-acetyl-6-methoxynaphthalene, are important intermediates in naproxen synthesis. N-Hydroxyphthalimide is shown here to be an efficient catalyst for oxidation to the hydroperoxide, 2-methoxy-6-(1-hydroperoxy-1-methylethyl)naphthalene, with a yield of 87%. However, the ketone and alcohol were obtained with lower yields, with a maximum yield of 13% for the ketone and 27% for the alcohol, using N-hydroxyphthalimide and Cu(II) acetylacetonate as a catalyst. The synthesis of the products 2-acetyl-6-methoxynaphthalene and 2-methoxy-6-(1-hydroxy-1-methylethyl)naphthalene via an initial oxidation step to the hydroperoxide followed by a hydroperoxide decomposition step is shown to be more efficient; the ketone and alcohol were obtained from 2-methoxy-6-(1-methylethyl)naphthalene with yields of 40 and 56%, respectively.

  DOI：

  10.1007/s00706-011-0630-3

文献信息

• Synthesis of Naphthalenediols by Aerobic Oxidation of Diisopropylnaphthalenes Catalyzed byN-Hydroxyphthalimide (NHPI)/α,α′-Azobisisobutyronitrile (AIBN)
  作者：Yasuhiro Aoki、Satoshi Sakaguchi、Yasutaka Ishii

  DOI：10.1002/adsc.200303168

  日期：2004.2

  Naphthalenediols were successfully synthesized in a one-pot reaction through the oxidation of diisopropylnaphthalenes with air catalyzed by N-hydroxyphthalimide (NHPI) combined with α,α′-azobisisobutyronitrile (AIBN) followed by decomposition with sulfuric acid. Thus, the oxidation of 2,6-diisopropylnaphthalene with air (20 atm) in the presence of AIBN (3 mol %) and NHPI (10 mol %) in CH3CN at 75 °C

  一锅反应成功地合成了萘二醇，方法是将N-羟基邻苯二甲酰亚胺（NHPI）与α，α'-偶氮二异丁腈（AIBN）结合催化空气氧化二异丙基萘，然后用硫酸分解。因此，在A3N（3 mol％）和NHPI（10 mol％）存在下于75°C的CH 3 CN中用空气（20 atm）氧化2,6-二异丙基萘21小时，然后用0.3 MH处理2 SO 4以92％的收率得到2，6-萘二醇。
• Copper (II) chloride / tetrabutylammonium bromide catalyzed oxidation of 2,6-diisopropylnaphthalene and 4,4′-diisopropylbiphenyl
  作者：Beata Orlińska、Jan Zawadiak

  DOI：10.2478/s11532-009-0134-8

  日期：2010.4.1

  The oxidation processes of 2,6-diisopropylnaphthalene and 4,4′-diisopropylbiphenyl with oxygen in the presence of a catalyst, composed of copper(II) chloride and tetrabutylammonium bromide, were investigated. It was found that, in essence, only one isopropyl group undergoes oxidation, and obtained mixtures contained mainly peroxide, alcohol, ketone and only small amounts of hydroperoxide.

  摘要 本文研究了在存在铜(II)氯化物和四丁基溴化铵催化剂的情况下，2,6-二异丙基萘和4,4'-二异丙基联苯与氧气的氧化过程。发现本质上只有一个异丙基基团发生氧化，并得到的混合物主要含有过氧化物、醇、酮和少量的过氧化氢。
• Substituent effects on13C and1H chemical shifts in 2-isopropyl- and 2,6-diisopropylnaphthalene and their oxidation products
  作者：Roman Mazurkiewicz、Zbigniew Stec、Jan Zawadiak

  DOI：10.1002/(sici)1097-458x(200003)38:3<213::aid-mrc617>3.0.co;2-g

  日期：2000.3

  naphthalenes with isopropyl, 2‐hydroxy‐2‐methylethyl and 2‐hydroperoxy‐2‐methylethyl substituents by the use of proton–proton decoupling, 2D H,H‐COSY and 2D‐C,H‐COSY techniques. The downhill simplex method was used for calculations of the best set of 13C and 1H incremental shifts. An excellent additivity of substituent effects was found for both, the 13C and 1H spectra of 2,6‐disubstituted naphthalenes. Copyright

  通过使用质子 - 质子去耦，2D 对三个具有异丙基、2-羟基-2-甲基乙基和 2-氢过氧-2-甲基乙基取代基的 2-取代和 6 个 2,6-二取代萘进行了 13C 和 1H 光谱分配H,H-COSY 和 2D-​​C,H-COSY 技术。下坡单纯形法用于计算 13C 和 1H 增量偏移的最佳集合。对于 2,6-二取代萘的 13C 和 1H 光谱，均发现了优异的取代基效应的可加性。版权所有 © 2000 John Wiley & Sons, Ltd.
• Process for producing polyhydroperoxy aromatic compound
  申请人：Mitsubishi Petrochemical Co., Ltd.

  公开号：US05196598A1

  公开（公告）日：1993-03-23

  A process for producing a polyhydroperoxy aromatic compound by oxidation of an aromatic hydrocarbon, e.g., 4,4'-diisopropylbiphenyl and 4,4'-diisopropylnaphthalene, with molecular oxygen is disclosed, in which the oxidation is carried out in the presence of a metal ion selected from cobalt, nickel, zinc and lead ions. Even in using a reaction apparatus made of an iron-containing metal generally employed in industry, a high conversion of secondary alkyl groups can be reached, and the desired polyhydroperoxy aromatic compound can be obtained in a high yield.

  本发明揭示了一种通过氧化芳香烃类化合物（例如4,4'-二异丙基联苯和4,4'-二异丙基萘）制备聚羟过氧基芳香化合物的方法，其中在钴、镍、锌和铅离子中选择一种金属离子的存在下进行氧化。即使使用通常在工业中使用的含铁金属制成的反应设备，也可以达到较高的次烷基转化率，并且可以高产得到所需的聚羟过氧基芳香化合物。
• Process for preparing hydroxynaphthalenes
  申请人：MITSUI PETROCHEMICAL INDUSTRIES, LTD.

  公开号：EP0260147A2

  公开（公告）日：1988-03-16

  Disclosed in accordance with the present invention are processes for the preparation of hydroperoxides and/or carbinols by liquid phase oxidation of secondary alkyl-­substituted naphthalenes with molecular oxygen, wherein the oxidation reaction is carried out by dissolving in the reaction mixture containing the secondary alkyl-­substituted naphthalenes at least 0.5 ppm in terms of metal, based on the starting secondary alkyl-substituted naphthalenes, of at least one compound of metal selected from the group consisting of palladium and gold, said metal compound being soluble in the reaction mixture of the secondary alkyl-substituted naphthalenes. When compared with the prior art processes using catalysts of non-homogeneous system, therefore, not only the amount of catalyst used can be minimized but also the rate of oxidation can be enhanced, and hence there can be obtained in a short period of time hydroperoxides and/or carbinols in high yields which are the oxidation products in accordance with the present invention. According to the present invention, the desired hydroperoxide can be obtained in high yields as well as in high purity from the hydroperoxides and/or carbinols obtained in the manner as mentioned above.

  根据本发明公开了通过仲烷基取代的萘与分子氧的液相氧化制备氢过氧化物和/或碳醇的工艺，其中氧化反应是通过在含有仲烷基取代的萘的反应混合物中溶解至少0.5ppm 的金属化合物，所述金属化合物可溶于仲烷基取代萘的反应混合物中。因此，与使用非均相体系催化剂的现有技术工艺相比，不仅可以最大限度地减少催化剂用量，而且可以提高氧化速率，从而可以在短时间内获得高产率的氢过氧化物和/或碳醇，它们是本发明的氧化产物。 根据本发明，可以从以上述方式获得的氢过氧化物和/或碳醇中高产率和高纯度地获得所需的氢过氧化物。