1-甲基-4-(1-甲基环己基)苯 | 14962-12-0

• 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-甲基-4-(1-甲基环己基)苯
• 英文名称: 4-(1-methylcyclohexyl)toluene
• 英文别名: 1-Methyl-4-(1-methylcyclohexyl)benzene
• CAS: 14962-12-0
• 化学式: C₁₄H₂₀
• 分子量: 188.313
• InChiKey: DMTXIQKUROZCRC-UHFFFAOYSA-N

物化性质

• 沸点：
  103-104 °C(Press: 2 Torr)
• 密度：
  0.9412 g/cm3

计算性质

• 辛醇/水分配系数(LogP)：
  5.4
• 重原子数：
  14
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.57
• 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-甲基-4-(1-甲基环己基)苯 在 chromium(VI) oxide 、 sodium hydroxide 、 硫酸 、 水 、 硝酸 、 乙酸酐 、 sodium hydrogensulfite 作用下， 以 水 为溶剂， 反应 13.5h， 生成 2-<2,3-Dihydro-6-(1-methylcyclohexyl)-3-oxo-1H-indol-2-yliden>-2,3-dihydro-6-(1-methylcyclohexyl)-1H-indol-3-on
  参考文献：
  名称：

  Meier, Helmut; Luettke, Wolfgang, Liebigs Annalen der Chemie, 1981, # 7, p. 1303 - 1333

  摘要：

  DOI：
• 作为产物：
  描述：

  (+/-)-trans-2-methylcyclohexanol 在 对甲苯磺酸 、 三乙胺 作用下， 以 四氯化碳 为溶剂， 反应 7.0h， 生成 1-甲基-4-(1-甲基环己基)苯
  参考文献：
  名称：

  Detailed Characterization of p-Toluenesulfonic Acid Monohydrate as a Convenient, Recoverable, Safe, and Selective Catalyst for Alkylation of the Aromatic Nucleus

  摘要：

  Alkylation of the aromatic nucleus, an important reaction in industry and synthetic organic chemistry, has traditionally been carried out by the well-known Friedel-Crafts reaction employing Lewis acid catalysts such as AlCl3 and BF3 or by using highly reactive organometallic reagents. Although protic acids such as anhydrous HF and concentrated H2SO4 have also been used in the alkylation of the aromatic nucleus, the notoriously corrosive, highly toxic, and hazardous nature of these agents has precluded their common use under ordinary laboratory conditions. Various organic sulfonic acids have, on occasion, been used as catalysts in Friedel-Crafts alkylations, but to our knowledge the chemistry and the scope of these reactions for common laboratory use have never been exploited in detail. In the present study we have characterized commercially available p-toluenesulfonic acid monohydrate (TsOH) as an efficient catalyst for the intermolecular coupling of the aromatic nucleus with activated alkyl halides, alkenes, or tosylates under mild conditions in an open atmosphere. In comparison to conventional Friedel-Crafts catalysts such as AlCl3, BF3, HF, and concentrated H2SO4, the extent of the formation of undesired products from side reactions such as transalkylation, polymerization, etc. was minimal with the TsOH-catalyzed reaction. The ability to recover and reuse the catalyst from the reaction mixtures, minimal generation of environmentally unfriendly waste, high specificity of the reaction, and the low cost of the catalyst are important advantages of the TsOH catalyst over the other conventional Friedel-Crafts catalysts.

  DOI：

  10.1021/jo971832r

文献信息

• Catalysts for the hydroalkylation of benzene, toluene and xylenes.
  作者：TSUTOMU KAMIYAMA、SABURO ENOMOTO、MASAMI INOUE

  DOI：10.1248/cpb.29.15

  日期：——

  The catalytic hydroalkylation of benzene over palladium and fused salt (NaCl-AlCl3) was examined under hydrogen pressure. The combination catalyst of palladium and fused salt showed good activity for hydroalkylation, providing cyclohexylbenzene as the main product, with a small amount of bicyclohexyl. With 0.24% palladium supported on alumina, suitable reaction conditions were : a temperature of 120-140°, and a reaction time of 5-10 hr in the presence of fused salt (NaCl-AlCl3 ; molar ratio 1 : 1). Under these conditions, the yields of cyclohexylbenzene and bicyclohexyl were 54.7 and 5.1%, respectively. This catalyst system was applied to the hydroalkylation of toluene, xylenes and trimethylbenzenes. Based on the behavior of the fused salt, we suggest that NaAlCl4 represents an active species in the hydroalkylation reaction.

  在氢气压力下检查了苯在钯和熔盐 (NaCl-AlCl3) 上的催化加氢烷基化反应。钯和熔盐的组合催化剂表现出良好的加氢烷基化活性，主要产物为环己基苯，并含有少量联环己基。对于负载在氧化铝上的0.24％钯，合适的反应条件为：温度120-140℃，在熔盐(NaCl-AlCl3；摩尔比1:1)存在下反应时间5-10小时。在此条件下，环己基苯和联环己基的收率分别为54.7%和5.1%。该催化剂体系应用于甲苯、二甲苯和三甲苯的加氢烷基化。根据熔盐的行为，我们认为 NaAlCl4 代表加氢烷基化反应中的活性物质。
• Obukhova, T. A.; Basaeva, N. N.; Betnev, A. F., Journal of Organic Chemistry USSR (English Translation), 1986, p. 351 - 353
  作者：Obukhova, T. A.、Basaeva, N. N.、Betnev, A. F.、Musabekov, Yu. Yu.、Mironov, G. S.

  DOI：——

  日期：——
• Voronenkov, V. V.; Dzyuba, I. B.; Kryukov, S. I., Journal of Organic Chemistry USSR (English Translation), 1990, vol. 26, # 12.2, p. 2236 - 2238
  作者：Voronenkov, V. V.、Dzyuba, I. B.、Kryukov, S. I.、Zhdankin, V. V.

  DOI：——

  日期：——
• [EN] OXIDATION OF METHYL-SUBSTITUTED BIPHENYL COMPOUNDS<br/>[FR] OXYDATION DE COMPOSÉS BIPHÉNYLE SUBSTITUÉS PAR MÉTHYLE
  申请人：EXXONMOBIL CHEMICAL PATENTS INC

  公开号：WO2017176391A3

  公开（公告）日：2018-07-26
• Batke, Birgit; Lauterbach, Gerlinde; Pritzkow, Wilhelm, Journal fur praktische Chemie (Leipzig 1954), 1988, vol. 330, # 4, p. 671 - 673
  作者：Batke, Birgit、Lauterbach, Gerlinde、Pritzkow, Wilhelm、Sebald, Frank、Voerckel, Volkmar

  DOI：——

  日期：——