2-isopropyl-2'-methoxybiphenyl | 31539-93-2

• 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: 2-isopropyl-2'-methoxybiphenyl
• 英文别名: 1-Methoxy-2-(2-propan-2-ylphenyl)benzene
• CAS: 31539-93-2
• 化学式: C₁₆H₁₈O
• 分子量: 226.318
• InChiKey: CCWWAMZNORVYKC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.6
• 重原子数：
  17
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  9.2
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  2-isopropyl-2'-methoxybiphenyl 在 氢溴酸 、 乙酸酐 作用下， 以 溶剂黄146 为溶剂， 生成 2'-isopropylbiphenyl-2-ol
  参考文献：
  名称：

  氢键对联苯内旋的影响的核磁共振研究

  摘要：

  已经通过核磁共振技术研究了关于几种联苯衍生物的枢轴键的内旋，使用位于不对称中心附近的异丙基中两个甲基的不同化学位移。比较了 2-甲氧基和 2-羟基衍生物的结果。溶剂效应在 2-羟基衍生物中显着。这些结果与取代基效应一起表明，围绕 2-羟基衍生物的枢轴键旋转的活化能略高于相应的甲基醚的事实可能归因于基态的稳定化。来自分子内 O-H…π 相互作用的存在。红外数据与上述结论一致。

  DOI：

  10.1246/bcsj.44.1683
• 作为产物：
  描述：

  2-异丙基苯胺 在 Cu-bronze 作用下， 生成 2-isopropyl-2'-methoxybiphenyl
  参考文献：
  名称：

  对位取代基对联苯衍生物转化率的影响。二、2-异丙基-2'-甲氧基联苯

  摘要：

  合成了九个 4,4'-取代的 2-异丙基-2'-甲氧基联苯，并检查了这些化合物的 NMR 光谱的温度依赖性。取代基对联苯骨架反转能垒的影响可以从共振稳定性和过渡态轴键的面外弯曲两个方面来解释。在后者中，给电子取代基使键弯曲更容易并降低了势垒，而吸电子基团则提高了势垒。

  DOI：

  10.1246/bcsj.44.266

文献信息

• Copper-Catalyzed Coupling of Triaryl- and Trialkylindium Reagents with Aryl Iodides and Bromides through Consecutive Transmetalations
  作者：Surendra Thapa、Santosh K. Gurung、Diane A. Dickie、Ramesh Giri

  DOI：10.1002/anie.201407586

  日期：2014.10.20

  An efficient copper(I)‐catalyzed coupling of triaryl and trialkylindium reagents with aryl iodides and bromides is reported. The reaction proceeds at low catalyst loadings (2 mol %) and generally only requires 0.33 equivalents of the triorganoindium reagent with respect to the aryl halide as all three organic nucleophilic moieties of the reagent are transferred to the products through consecutive transmetalations

  据报道，三芳基和三烷基铟试剂与芳基碘化物和溴化物的高效铜（I）催化偶联。反应在低催化剂负载量（2mol％）下进行，并且相对于芳基卤化物，通常仅需要0.33当量的三有机铟试剂，因为试剂的所有三个有机亲核部分都通过连续的重金属化作用转移到产物中。该反应耐受各种官能团和空间受阻的底物。此外，涉及潜在反应中间体的合成和表征的初步机理研究提供了构成催化循环的基本步骤的一瞥。
• Efficient Synthesis of Sterically Crowded Biaryls by Palladium-Phosphinous Acid-Catalyzed Cross-Coupling of Aryl Halides and Aryl Grignards
  作者：Christian Wolf、Hanhui Xu

  DOI：10.1021/jo701893m

  日期：2008.1.1

  A series of sterically hindered biaryls have been obtained by palladium- and nickel-phosphinous acid-catalyzed Kumada−Corriu cross-coupling of ortho-substituted aryl halides and Grignard reagents. This method allows formation of di- and tri-ortho-substituted biaryls in 87−98% yield under mild reaction conditions even when electron-rich aryl chlorides are used. The reaction also proceeds with aryl iodides

  通过钯和镍次膦酸催化的正取代芳基卤化物和Grignard试剂的Kumada-Corriu交叉偶联，获得了一系列位阻联芳基。这种方法即使在使用富电子的芳基氯化物的条件下，也可以在温和的反应条件下以87-98％的产率形成二和三邻位取代的联芳基。该反应还会在-20°C的条件下与芳基碘化物进行，在这些条件下，可以耐受通常与格氏试剂不相容的官能团。
• CETP INHIBITORS DERIVED FROM BENZOXAZOLE ARYLAMIDES
  申请人：Hunt Julianne A.

  公开号：US20100184719A1

  公开（公告）日：2010-07-22

  Compounds having the structure of Formula I, including pharmaceutically acceptable salts of the compounds, are potent CETP inhibitors, and are useful for raising HDL-cholesterol, reducing LDL-cholesterol, and for treating or preventing atherosclerosis. In formula I, A-B is an arylamide moiety.

  具有公式I结构的化合物，包括化合物的药学上可接受的盐，是有效的CETP抑制剂，可用于提高HDL胆固醇，降低LDL胆固醇，并用于治疗或预防动脉粥样硬化。 在公式I中，A-B是芳香酰胺基团。
• A mild robust generic protocol for the Suzuki reaction using an air stable catalyst
  作者：Jonathan D. Moseley、Paul M. Murray、Edward R. Turp、Simon N.G. Tyler、Ross T. Burn

  DOI：10.1016/j.tet.2012.05.030

  日期：2012.7

  A mild but robust procedure has been developed as a first pass generic protocol for the Suzuki-Miyaura reaction. The protocol employs an air stable palladium pre-catalyst at low loading (<= 1 mol %) in aqueous solvent mixtures at moderate temperature using potassium carbonate as base. Under these mild conditions, most aryl bromides will react with sterically and electronically demanding aryl boronic acids to give complete conversion to the product biphenyls in less than 1 h. Aryl chlorides are also fully converted in most cases either under identical conditions in 8-24 h, or in 2 h at elevated temperature. A further advantage of these mild conditions of moderate temperature, weak base and benign solvent is that sensitive functional groups and structural motifs are well tolerated. In addition, the lipophilic biphenyl products are readily isolated after a simple work-up procedure. These generic conditions are ideal for proof of transformation, and as the starting point for development and optimization of a specific process. The discovery and fine-tuning of this generic protocol will be presented, supported extensively by examples to illustrate its scope and utility. (C) 2012 Elsevier Ltd. All rights reserved.
• Palladium-Catalyzed One-Pot Cross-Coupling of Phenols Using Nonafluorobutanesulfonyl Fluoride
  作者：Shuji Akai、Takashi Ikawa、Kozumo Saito

  DOI：10.1055/s-0032-1317076

  日期：——

  Palladium-catalyzed coupling reactions, such as the Suzuki-Miyaura, Sonogashira, Stille, and Buchwald-Hartwig couplings, of phenols using nonafluorobutanesulfonyl fluoride (NfF) are described. These reactions proceeded through the in situ nonaflation of phenols.