2-(4-butylphenyl)naphthalene | 1075754-29-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 2-(4-butylphenyl)naphthalene
• 英文别名: 2-(4-n-butylphenyl)naphthalene
• CAS: 1075754-29-8
• 化学式: C₂₀H₂₀
• 分子量: 260.379
• InChiKey: KVLKOXCQINUYAK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.85
• 重原子数：
  20.0
• 可旋转键数：
  4.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  0.0
• 氢给体数：
  0.0
• 氢受体数：
  0.0

反应信息

• 作为产物：
  描述：

  (4-butylphenyl)(naphthalen-2-yl)methanone 在 bis(1,5-cyclooctadiene)nickel (0) 、 IMes^Me hydrochloride 、 sodium t-butanolate 作用下， 以 甲苯 为溶剂， 反应 18.0h， 以54%的产率得到2-(4-butylphenyl)naphthalene
  参考文献：
  名称：

  通过碳-碳键的断裂镍介导的简单无应变酮的脱羰

  摘要：

  尽管醛的脱羰方法取得了进展，但酮的脱羰取得的成功有限，因为该过程需要激活两个惰性碳-碳键。迄今为止报道的所有简单的无应变酮的脱羰反应都需要添加化学计量的铑配合物。我们在此报告了镍/N-杂环卡宾介导的简单二芳基酮的脱羰。基于给电子基团和吸电子基团的存在，该反应显示出独特的加速效果。

  DOI：

  10.1021/jacs.6b12293

文献信息

• Nickel-Catalyzed Cross-Coupling of Aryl Phosphates with Arylboronic Acids
  作者：Hu Chen、Zhongbin Huang、Xiaoming Hu、Guo Tang、Pengxiang Xu、Yufen Zhao、Chien-Hong Cheng

  DOI：10.1021/jo2000034

  日期：2011.4.1

  The Suzuki−Miyaura cross-coupling of aryl phosphates using Ni(PCy3)2Cl2 as an inexpensive, bench-stable catalyst is described. Broad substrate scope and high efficiency are demonstrated by the syntheses of more than 40 biaryls and by constructing complex organic molecules. The poor reactivity of aryl phosphates relative to aryl halides is successfully employed to construct polyarenes by selective cross-coupling

  描述了使用Ni（PCy 3）2 Cl 2作为廉价，稳定的催化剂对芳基磷酸酯进行的Suzuki-Miyaura交叉偶联。超过40个联芳基的合成以及构建复杂的有机分子证明了广泛的底物范围和高效率。通过使用Pd和Ni催化剂进行选择性交叉偶联，成功地将磷酸芳基酯相对于芳基卤化物的不良反应性用于构建聚芳烃。
• Mutual Activation: Suzuki-Miyaura Coupling through Direct Cleavage of the sp2 CO Bond of Naphtholate
  作者：Da-Gang Yu、Zhang-Jie Shi

  DOI：10.1002/anie.201101461

  日期：2011.7.25

  Working together: A new approach of mutual activation between naphtholates and aryl boronic acid derivatives by the formation of borates to facilitate the Suzuki–Miyaura coupling through direct cleavage of the sp2 CO bond by nickel catalysis is described (see scheme; R′: annulated ring system). Various naphtholates and aryl boronic acid derivatives could be directly coupled in good yields.

  一起工作：由硼酸盐的形成相互活化的naphtholates和芳基硼酸衍生物之间的一种新方法，以促进通过SP的直接裂解铃木-宫浦偶合2 ç  Ò由镍催化键被描述（参见方案; R' ：环形环系统）。各种萘甲酸酯和芳基硼酸衍生物可以以良好的产率直接偶联。
• Temperature‐Controlled Mechanochemistry for the Nickel‐Catalyzed Suzuki–Miyaura‐Type Coupling of Aryl Sulfamates via Ball Milling and Twin‐Screw Extrusion.**
  作者：Robert R. A. Bolt、Sarah E. Raby‐Buck、Katharine Ingram、Jamie A. Leitch、Duncan L. Browne

  DOI：10.1002/anie.202210508

  日期：2022.11.2

  The nickel catalyzed Suzuki–Miyaura-type coupling of aryl sulfamates and boronic acid derivatives enabled by temperature-controlled mechanochemistry via the development of a programmable PID-controlled jar heater is reported. This base-metal-catalyzed, solvent-free, all-under-air protocol was also scaled 200-fold using twin-screw extrusion technology affording decagram quantities of material.

  报道了通过开发可编程 PID 控制的罐式加热器，通过温度控制的机械化学实现了镍催化的 Suzuki-Miyaura 型芳基氨基磺酸酯和硼酸衍生物的偶联。这种贱金属催化、无溶剂、全在空气中的协议也使用双螺杆挤出技术扩大了 200 倍，提供了十克数量的材料。
• Biaryl Construction via Ni-Catalyzed C−O Activation of Phenolic Carboxylates
  作者：Bing-Tao Guan、Yang Wang、Bi-Jie Li、Da-Gang Yu、Zhang-Jie Shi

  DOI：10.1021/ja8056503

  日期：2008.11.5

  Biaryl scaffolds were constructed via Ni-catalyzed aryl C-O activation by avoiding cleavage of the more reactive acyl C-O bond aryl carboxylates. Now aryl esters, in general, can be successfully employed in cross-coupling reactions for the first time. The substrate scope and synthetic utility of the chemistry were demonstrated by the syntheses of more than 40 biaryls and by constructing complex organic molecules. Water was observed to play an important role in facilitating this transformation.