2-(4-methylphenyl)bicyclo[2.2.1]heptane | 58534-83-1

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 异戊烯醇脂质
• 英文名称: 2-(4-methylphenyl)bicyclo[2.2.1]heptane
• 英文别名: 4-(2-norbornyl)toluene；p-Tolylnorbornan
• CAS: 58534-83-1
• 化学式: C₁₄H₁₈
• 分子量: 186.297
• InChiKey: YBLLKDQCAWXYAC-UHFFFAOYSA-N

物化性质

• 沸点：
  283.1±10.0 °C(Predicted)
• 密度：
  1.003±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.6
• 重原子数：
  14
• 可旋转键数：
  1
• 环数：
  3.0
• 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：

  降冰片烯 、 4-碘甲苯 在 甲酸 、 C₄₆H₄₈Cl₂N₂O₂Pd₂ 、 三乙胺 作用下， 以 氘代二甲亚砜 为溶剂， 反应 240.0h， 以52%的产率得到2-(4-methylphenyl)bicyclo[2.2.1]heptane
  参考文献：
  名称：

  Catalytic properties of chiral terpenoid CN-palladacycle in the C—C bond forming reactions

  摘要：

  手性樟脑衍生的 CN-palladacycle 在温和条件下对降冰片烯的铃木交叉耦合和加氢反应具有很高的催化活性。

  DOI：

  10.1007/s11172-015-0882-x

文献信息

• Synthesis and catalytic activity of a complex of 1,1´-bis-isoquinoline N,N´-dioxide with PdCl2
  作者：L. A. Bulygina、N. S. Khrushcheva、V. I. Sokolov、A. A. Khodak

  DOI：10.1007/s11172-015-0880-z

  日期：2015.2

  A novel complex of 1,1´-bis-isoquinoline N,N´-dioxide with PdCl2 was synthesized. This complex efficiently catalyzes the Suzuki cross-couplings and hydroarylation of norbornene.

  合成了一种1,1'-双异喹啉N,N'-二氧化物与PdCl2的新的配合物。该配合物有效催化了诺尔本烯的铃木交叉偶联反应和氢芳基化反应。
• Cyclopalladated complex of 1-ferrocenylisoquinoline
  作者：L. A. Bulygina、N. S. Khrushcheva、A. S. Peregudov、V. I. Sokolov

  DOI：10.1007/s11172-015-0834-5

  日期：2015.1

  A new dimeric cyclopalladated ferrocenyl complex di-µ -chloro-bis[2-(1-isoquinolinyl)ferrocenyl](C,N)dipalladium was obtained and characterized. Its catalytic properties in the Heck and Suzuki reactions (including a solid-phase version), as well as in hydroarylation of norbornene, were studied.

  研究人员获得了一种新的二聚环钯化二茂铁络合物二-µ-氯-双[2-(1-异喹啉基)二茂铁](C,N)二钯，并对其进行了表征。研究了它在赫克反应和铃木反应（包括固相反应）以及降冰片烯加氢反应中的催化特性。
• Asymmetric hydroarylation of norbornene derivatives catalyzed by palladium complexes of chiral quinolinyl-oxazolines
  作者：Xin-Yan Wu、Hua-Dong Xu、Fang-Yi Tang、Qi-Lin Zhou

  DOI：10.1016/s0957-4166(01)00436-0

  日期：2001.10

  palladium-catalyzed Heck-type hydroarylation of norbornene and its derivatives. The ligands with a medium sized alkyl group on the oxazoline ring provided higher enantioselectivities. The presence of electron-donating substituents on the aryl iodide increased the selectivity and the yield of the reactions. The configuration of (−)-exo-2-phenylbicyclo[2.2.1]heptane has been assigned as (1R,2R).

  已发现手性喹啉基-恶唑啉是降冰片烯及其衍生物的对映选择性钯催化的Heck型加氢芳基化反应中的有效配体。在恶唑啉环上具有中等大小烷基的配体提供更高的对映选择性。芳基碘化物上供电子性取代基的存在增加了反应的选择性和产率。（-）-外-2-基苯基二环[2.2.1]庚烷的构型已被指定为（1 R，2 R）。
• Detailed Characterization of <i>p</i>-Toluenesulfonic Acid Monohydrate as a Convenient, Recoverable, Safe, and Selective Catalyst for Alkylation of the Aromatic Nucleus
  作者：Mathew P. D. Mahindaratne、Kandatege Wimalasena

  DOI：10.1021/jo971832r

  日期：1998.5.1

  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.