1-甲基-3-(1-甲基-环己基)-苯 | 14962-11-9

• 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-3-(1-甲基-环己基)-苯
• 英文名称: 3-(1-Methylcyclohexyl)toluol
• 英文别名: 1-Methyl-3-(1-methyl-cyclohexyl)-benzol；Benzene, 1-methyl-3-(1-methylcyclohexyl)-；1-methyl-3-(1-methylcyclohexyl)benzene
• CAS: 14962-11-9
• 化学式: C₁₄H₂₀
• 分子量: 188.313
• InChiKey: PZNNCEDGJDNCFI-UHFFFAOYSA-N

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-3-(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

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

  DOI：——

  日期：——
• Reetz, Manfred T.; Westermann, Juergen; Steinbach, Rainer, Angewandte Chemie, 1980, vol. 92, # 11, p. 933 - 934
  作者：Reetz, Manfred T.、Westermann, Juergen、Steinbach, Rainer

  DOI：——

  日期：——
• Nickel-Catalyzed Carbon–Carbon Bond-Forming Reactions of Unactivated Tertiary Alkyl Halides: Suzuki Arylations
  作者：Susan L. Zultanski、Gregory C. Fu

  DOI：10.1021/ja311669p

  日期：2013.1.16

  The first Suzuki cross-couplings of unactivated tertiary alkyl electrophiles are described. The method employs a readily accessible catalyst (NiBr2 center dot diglyme/4,4'-di-tert-butyl-2,2'-bipyridine, both commercially available) and represents the initial example of the use of a group 10 catalyst to cross-couple unactivated tertiary electrophiles to form C-C bonds. This approach to the synthesis of all-carbon quaternary carbon centers does not suffer from isomerization of the, alkyl group, in contrast with the umpolung strategy for this bond construction (cross-coupling of a tertiary alkylmetal with an aryl electrophile). Preliminary mechanistic studies are consistent with the generation of a radical intermediate along the reaction pathway.
• REETZ M. T.; WESTERMANN J.; STEINBACH R., ANGEW. CHEM., 1980, 92, NO 11, 933-934
  作者：REETZ M. T.、 WESTERMANN J.、 STEINBACH R.

  DOI：——

  日期：——
• PASHAEV T. A.; PASHAEVA F. A.; SALIMOVA B. S., AZEHRB. KIMJA ZH., AZERB. XIM. ZH. <AZKZ-AU>, 1975, HO 3, 37-40
  作者：PASHAEV T. A.、 PASHAEVA F. A.、 SALIMOVA B. S.

  DOI：——

  日期：——