6-乙酰基-2-异丙基萘 | 107208-69-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 中文名称: 6-乙酰基-2-异丙基萘
• 英文名称: 1-(6-(1-methylethyl)naphthalen-2-yl)ethanone
• 英文别名: 6-acetyl-2-isopropylnaphthalene；1-(6-propan-2-ylnaphthalen-2-yl)ethanone
• CAS: 107208-69-5
• 化学式: C₁₅H₁₆O
• 分子量: 212.291
• InChiKey: OLUWJUQTHLYMKJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4
• 重原子数：
  16
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  17.1
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  6-乙酰基-2-异丙基萘 在 N-羟基邻苯二甲酰亚胺 、 偶氮二异丁腈 、 氧气 、 硫酸 作用下， 以 乙腈 为溶剂， 反应 16.0h， 以75%的产率得到6-乙酰基-2-萘酚
  参考文献：
  名称：

  Synthesis of 6-hydroxy-2-naphthoic acid from 2,6-diisopropylnaphthalene using NHPI as a key catalyst

  摘要：

  A new strategy to 6-hydroxy-2-naphthoic acid (HNPA) and 4-hydroxybenzoic acid from 2,6-diisopropylnaphthalene and p-cymene, respectively, was developed using the NHPI-catalyzed aerobic oxidation as a principal reaction. 2,6-Diisopropylnaphthalene was oxidized by the oxidation with O-2 (1 atm) by NHPI (10 mol %) combined with Co(OAc)(2) (0.5 mol %) to give 6-acetyl-2 -isopropylnaphthalene, which then was converted to 6-isopropyl-2-naphthoic acid Under O-2 (1 atm) in the presence of Co(OAc)(2) (0.5 mol %) and Mn(OAc)(2) (0.5 mol %), Esterification of the resulting acid followed by the aerobic oxidation produced methyl 6-hydroxy-2-naphthoate whose hydrolysis led to the desired HNPA. An alternative route involves the oxidation of 6-acetyl-2-isopropylnaphthalene to 6-acetyl-2-naphthol on which subsequent oxidation and deacetylation gave HNPA. This method was Successfully extended to the synthesis of 4-hydroxybenzoic acid from p-cymene. (C) 2009 Elsevier Ltd, All rights reserved.

  DOI：

  10.1016/j.tet.2009.03.013
• 作为产物：
  描述：

  2,6-二异丙基萘 在 manganese(III)-5,10,15,20-tetrakis(pentafluorophenyl)porphyrin chloride 、 亚碘酰苯 作用下， 以 乙腈 为溶剂， 以10 %的产率得到6-乙酰基-2-异丙基萘
  参考文献：
  名称：

  Mn(III)-卟啉催化萘衍生物的氧化功能化

  摘要：

  报道了由含氟卟啉 Mn(TFPP)Cl 或不含氟卟啉 Mn(TPP)Cl 催化的萘及其衍生物的氧化功能化。发现催化剂极大地影响氧化功能化反应。这些研究将为金属卟啉催化的C-H键氧化功能化的进一步发展提供有价值的参考。

  DOI：

  10.1016/j.tetlet.2023.154535

文献信息

• Selective Oxidation of Acetophenones Bearing Various Functional Groups to Benzoic Acid Derivatives with Molecular Oxygen
  作者：Ryota Nakamura、Yasushi Obora、Yasutaka Ishii

  DOI：10.1002/adsc.200900099

  日期：2009.7

  Acetophenones substituted by alkyl, alkoxy, acetoxy, and halogen groups were selectively oxidized with molecular oxygen to the corresponding benzoic acids by using the N,N′,N′′‐trihydroxyisocyanuric acid (THICA)/cobalt(II) acetate [Co(OAc)2] and THICA/Co(OAc)2/manganese(II) acetate [Mn(OAc)2]. For example, 4‐methylacetophenone was selectively oxidized with molecular oxygen to 4‐acetylbenzoic acid (85%)

  通过使用N，N'，N''-三羟基异氰尿酸（THICA）/乙酸钴（II）[Co（OAc ）2 ]和THICA / Co（OAc）2 /乙酸锰（II）[Mn（OAc）2 ]。例如，4-甲基苯乙酮被分子氧选择性地氧化为THICA / Co（OAc）2氧化为4-乙酰基苯甲酸（85％），被Mn（OAc）2氧化为4-甲基苯甲酸（93％），而对苯二甲酸被用THICA / Co（OAc）2 / Mn（OAc）2以93％的比例获得催化系统。有趣的是，芳香环上的乙酰基可通过极少量的Mn（OAc）2有效地转化为相应的羧酸，并且本方法提供了通向常规常规方法难以制备的乙酰基苯甲酸的通用途径方法。
• 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。
• Verfahren zur selektiven Acylierung aromatischer Verbindungen
  申请人：RÜTGERSWERKE AKTIENGESELLSCHAFT

  公开号：EP0203276A1

  公开（公告）日：1986-12-03

  Alkyl-oder arylsubstituierte Aromaten werden acyliert durch Umsetzung mit Carbonsäuren oder Carbonsäureanhydriden, -estern oder -halogeniden bei Temperaturen im Bereich von -50 bis +50 °C in kondensiertem Fluorwasserstoff.

  烷基或芳基取代的芳烃通过与羧酸或羧酸酸酐、酯或卤化物在-50 至 +50 °C的温度下在缩合氟化氢中发生反应而酰化。
• Studies on calcined cow bone and pyrolyzed wood, suitable supports for immobilizing hybrid nano particles of Co-Mn as new catalysts for oxidation of 2,6-diisopropyl naphthalene
  作者：Atefeh Mardani Ghahfarrokhi、Parisa Moshiri、Mehran Ghiaci

  DOI：10.1016/j.apcata.2013.02.013

  日期：2013.4

  Catalytic oxidation of 2,6-diisopropylnaphthalene (2,6-DIPN) to 2,6-naphthalene dicarboxylic acid (2,6-NDCA) was studied with two new catalysts prepared by immobilization of Co/Mn nano-hybrid particles over calcined cow bone, and pyrolyzed wood. The catalysts have the advantage of very cheap supports, and easy catalyst recovery. The effects of Co/Mn atomic ratio, reaction time and temperature, oxygen pressure, amount of catalyst, and the support on the conversion of 2,6-DIPN and product/intermediate yields were investigated. There was an interesting synergistic effect of cobalt and manganese catalysts. The maximum product (2,6-NDCA) yield was 100%, obtained at a Co/Mn atomic ratio of 10 supported on pyrolyzed wood. Lower cobalt concentration resulted the lower 2,6-NDCA yield, which was ascribed to the intermediate products formation. The catalysts were characterized in detail by SEM/EDS, BET surface area, and TEM measurements. Transmission electron microscopy (TEM) measurements indicated nanoparticles (diameter of about 2-5 nm) on the surface of the supports. (C) 2013 Elsevier B.V. All rights reserved.
• ——
  作者：STEINBACH R.、 RUPPERT I.、 SCHLICH K.

  DOI：——

  日期：——