(4-methylphenyl)cycloheptane | 92298-88-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: (4-methylphenyl)cycloheptane
• 英文别名: p-tolylcycloheptane
• CAS: 92298-88-9
• 化学式: C₁₄H₂₀
• 分子量: 188.313
• InChiKey: ZSPRDOHWTFSGKJ-UHFFFAOYSA-N

物化性质

• 沸点：
  284.8±10.0 °C(Predicted)
• 密度：
  0.920±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.5
• 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：

  对溴甲苯 生成 (4-methylphenyl)cycloheptane
  参考文献：
  名称：

  BATKE, BIRGIT;LAUTERBACH, GERLINDE;PRITZKOW, WILHELM;SEBALD, FRANK;VOERCK+, J. PRAKT. CHEM., 330,(1988) N 4, C. 671-673

  摘要：

  DOI：

文献信息

• Dilithium Amides as a Modular Bis-Anionic Ligand Platform for Iron-Catalyzed Cross-Coupling
  作者：Peter G. N. Neate、Bufan Zhang、Jessica Conforti、William W. Brennessel、Michael L. Neidig

  DOI：10.1021/acs.orglett.1c02053

  日期：2021.8.6

  Dilithium amides have been developed as a bespoke and general ligand for iron-catalyzed Kumada–Tamao–Corriu cross-coupling reactions, their design taking inspiration from previous mechanistic and structural studies. They allow for the cross-coupling of alkyl Grignard reagents with sp2-hybridized electrophiles as well as aryl Grignard reagents with sp3-hybridized electrophiles. This represents a rare

  氨基二锂已被开发为铁催化的 Kumada-Tamao-Corriu 交叉偶联反应的定制和通用配体，其设计灵感来自先前的机械和结构研究。它们允许烷基格氏试剂与 sp 2杂化亲电试剂以及芳基格氏试剂与 sp 3杂化亲电试剂交叉偶联。这代表了一个罕见的例子，即单一铁催化系统在不同的偶联反应中有效，而无需对催化方案进行重大修改，并且操作简单。
• Iron-Catalyzed Suzuki–Miyaura Cross-Coupling Reactions between Alkyl Halides and Unactivated Arylboronic Esters
  作者：Michael P. Crockett、Chet C. Tyrol、Alexander S. Wong、Bo Li、Jeffery A. Byers

  DOI：10.1021/acs.orglett.8b02184

  日期：2018.9.7

  An iron-catalyzed cross-coupling reaction between alkyl halides and arylboronic esters was developed that does not involve activation of the boronic ester with alkyllithium reagents nor requires magnesium additives. A combination of experimental and theoretical investigations revealed that lithium amide bases coupled with iron complexes containing deprotonated cyanobis(oxazoline) ligands were best

  已开发出烷基卤化物与芳基硼酸酯之间铁催化的交叉偶联反应，该反应不涉及用烷基锂试剂活化硼酸酯，也不需要镁添加剂。实验和理论研究的组合表明，酰胺基锂与含去质子化的氰基双（恶唑啉）配体的铁配合物结合，在催化交叉偶联反应中最能获得高产率（最高89％）。机械研究暗示了以碳为中心的自由基中间体，并强调了避免导致铁聚集的条件的至关重要。新的铁催化的Suzuki-Miyaura反应用于最短的药物合成Cinacalcet合成。
• The first iron-catalysed aluminium-variant Negishi coupling: critical effect of co-existing salts on the dynamic equilibrium of arylaluminium species and their reactivity
  作者：Shintaro Kawamura、Kentaro Ishizuka、Hikaru Takaya、Masaharu Nakamura

  DOI：10.1039/c0cc01216e

  日期：——

  The first example of an iron-catalysed Negishi coupling between arylaluminium reagents and alkyl halides illustrates that the co-existing salts highly influence the dynamic equilibrium of the organoaluminium species, and have a critical effect on the reactivity and selectivity of the coupling reaction.

  第一个铁催化的Negishi偶联反应示例，即芳基铝试剂与烷基卤化物的反应，表明共存的盐类对有机铝物种的动态平衡产生强烈影响，并对此偶联反应的活性和选择性具有关键作用。
• Highly nucleophilic dipropanolamine chelated boron reagents for aryl-transmetallation to iron complexes
  作者：Jay J. Dunsford、Ewan R. Clark、Michael J. Ingleson

  DOI：10.1039/c5dt03835a

  日期：——

  New arylborates chelated by dipropanolamine are readily synthesised from boronic acids and demonstrated to be highly nucleophilic reagents.

  新的二丙醇胺螯合基芳基硼酸酯可从硼酸制备而成，并且被证明是高亲核试剂。
• Efficient cross-coupling of aryl Grignard reagents with alkyl halides by recyclable ionic iron(iii) complexes bearing a bis(phenol)-functionalized benzimidazolium cation
  作者：Chong-Liang Xia、Cun-Fei Xie、Yu-Feng Wu、Hong-Mei Sun、Qi Shen、Yong Zhang

  DOI：10.1039/c3ob41376d

  日期：——

  designed and used to prepare ionic iron(III) complexes of the type [H3L][FeX4] (X = Cl, 2; X = Br, 3). Both 2 and 3 were characterized by elemental analysis, Raman spectroscopy, electrospray ionization mass spectrometry and X-ray crystallography. The catalytic performances of 2 and 3 in cross-coupling reactions using aryl Grignard reagents with primary and secondary alkyl halides bearing β-hydrogens were

  设计了一种新型的双（苯酚）官能化苯并咪唑鎓盐1,3-双（3,5-二叔丁基-2-羟基苄基）苯并咪唑鎓氯化物（H 3 LCl，1），并用于制备离子铁（III）[H 3 L] [FeX 4 ]类型的络合物（X ＝ Cl，2； X ＝ Br，3）。既2和3进行了元素分析，拉曼光谱，电喷雾电离质谱法和X-射线晶体学进行了表征。2和3的催化性能用芳基格氏试剂与带有β-氢的伯烷基卤和仲烷基卤的交叉偶联反应进行了研究。该分析表明，络合物2具有烷基氯介导的偶联的良好潜力。相比之下，配合物3显示出稍低的催化活性。倾析出包含在醚层中的产物后，可以将络合物2循环至少八次而不会显着降低催化活性。