(2-methoxyphenyl)(naphthalen-2-yl)methanol

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: (2-methoxyphenyl)(naphthalen-2-yl)methanol
• 英文别名: 2-methoxyphenyl(2-naphthyl)methanol；2-methoxyphenyl-2-naphthylmethanol；(2-Methoxyphenyl)-naphthalen-2-ylmethanol
• 化学式: C₁₈H₁₆O₂
• 分子量: 264.324
• InChiKey: YIXXGTUPSKPPDV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4
• 重原子数：
  20
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.11
• 拓扑面积：
  29.5
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (2-methoxyphenyl)(naphthalen-2-yl)methanol 在 三乙基硅烷 、 三溴化硼 、 碳酸氢钠 、 三氟乙酸 作用下， 以 二氯甲烷 为溶剂， 反应 1.0h， 生成 2-((naphthalen-2-yl)methyl)phenol
  参考文献：
  名称：

  4,4′-Unsymmetrically substituted 3,3′-biphenyl alpha helical proteomimetics as potential coactivator binding inhibitors

  摘要：

  A series of unsymmetrically substituted biphenyl compounds was designed as alpha helical proteomimetics with the aim of inhibiting the binding of coactivator proteins to the nuclear hormone receptor coactivator binding domain. These compounds were synthesized in good overall yields in seven steps starting from 2-bromoanisole. The final products were evaluated using cotransfection reporter gene assays and mammalian two-hybrid competitive inhibition assays to demonstrate their effectiveness as competitive binding inhibitors. The results from this study indicate that these proteomimetics possess the ability to inhibit coactivator-receptor interactions, but via a mixed mode of inhibition. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2013.10.051
• 作为产物：
  描述：

  2-溴苯甲醚 、 2-萘甲醛 在 碘 、 magnesium 作用下， 以 四氢呋喃 为溶剂， 反应 6.17h， 以75%的产率得到(2-methoxyphenyl)(naphthalen-2-yl)methanol
  参考文献：
  名称：

  4,4′-Unsymmetrically substituted 3,3′-biphenyl alpha helical proteomimetics as potential coactivator binding inhibitors

  摘要：

  A series of unsymmetrically substituted biphenyl compounds was designed as alpha helical proteomimetics with the aim of inhibiting the binding of coactivator proteins to the nuclear hormone receptor coactivator binding domain. These compounds were synthesized in good overall yields in seven steps starting from 2-bromoanisole. The final products were evaluated using cotransfection reporter gene assays and mammalian two-hybrid competitive inhibition assays to demonstrate their effectiveness as competitive binding inhibitors. The results from this study indicate that these proteomimetics possess the ability to inhibit coactivator-receptor interactions, but via a mixed mode of inhibition. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2013.10.051

文献信息

• Addition reaction of arylboronic acids to aldehydes and α,β-unsaturated carbonyl compounds catalyzed by conventional palladium complexes in the presence of chloroform
  作者：Tetsuya Yamamoto、Michiko Iizuka、Hiroto Takenaka、Tetsuo Ohta、Yoshihiko Ito

  DOI：10.1016/j.jorganchem.2008.12.032

  日期：2009.4

  Arylboronic acids react with aldehydes and α,β-unsaturated carbonyl compounds in the presence of a base and a catalytic amount of a palladium(0) complex with chloroform, affording the corresponding addition products in good yields, and chiral benzhydrol was obtained with up to 43% e.e. using (S,S)-bppm as a ligand. General palladium complexes have no catalytic activity without chloroform. Because chloroform

  芳基硼酸在碱和催化量的钯（0）与氯仿的存在下，与醛和α，β-不饱和羰基化合物反应，以高收率提供相应的加成产物，并获得了最高使用（S，S）-bppm作为配体的ee为43％。普通的钯配合物没有氯仿就没有催化活性。因为氯仿对于该反应是必不可少的，所以二氯甲基钯（II）会促进这些反应。
• Introducing Water and Deep Eutectic Solvents in Organosodium Chemistry: Chemoselective Nucleophilic Functionalizations in Air
  作者：Giuseppe Dilauro、Cosimo Luccarelli、Andrea F. Quivelli、Paola Vitale、Filippo M. Perna、Vito Capriati

  DOI：10.1002/anie.202304720

  日期：2023.7.24

  Organosodium compounds, generated by the oxidative addition of a C−Cl bond to Na, a halogen/Na exchange, or by direct sodiation using Na bricks or neopentylsodium in hexane, have been intercepted by various electrophiles, when working “on water” or in eutectic mixtures. These reactions display a broad substrate scope, under hydrous conditions at room temperature, short reaction times (20 s), high chemoselectivity

  有机钠化合物是通过 C−Cl 键与 Na 的氧化加成、卤素/Na 交换或通过在己烷中使用钠砖或新戊基钠直接钠化而生成的，在“对水”或在水中工作时，已被各种亲电子试剂拦截。低共熔混合物。这些反应显示出广泛的底物范围，在室温含水条件下，反应时间短（20秒），化学选择性高，并且它们也是可扩展的。
• Efficient 1,2-Addition of Aryl- and Alkenylboronic Acids to Aldehydes Catalyzed by the Palladium/Thioether−Imidazolinium Chloride System
  作者：Masami Kuriyama、Rumiko Shimazawa、Ryuichi Shirai

  DOI：10.1021/jo7020983

  日期：2008.2.1

  [GRAPHICS]The high level of catalyst performance was attainable in the palladium-catalyzed 1,2-addition of aryl-, heteroaryl-, and alkenylboronic acids to aromatic, heteroaromatic, and aliphatic aldehydes using thioether-imidazolinium chloride L5 as a heterobidentate carbene ligand precursor.
• Palladium-catalyzed arylation of aldehydes with bromo-substituted 1,3-diaryl-imidazoline carbene ligand
  作者：Tetsuya Yamamoto、Takuma Furusawa、Azamat Zhumagazin、Tetsu Yamakawa、Yohei Oe、Tetsuo Ohta

  DOI：10.1016/j.tet.2014.11.051

  日期：2015.1

  The combination of 0 valent palladium precursor and bromo-substituted 1,3-diaryl-imidazoline carbene ligand precursor such as 1-(2-bromophenyl)-3-(2,6-diisopropylphenyl)-imidazolinium chloride 1a exhibited high catalytic activity for the 1,2-addition of arylboronic acids to aldehydes including aqueous formaldehyde. (C) 2014 Elsevier Ltd. All rights reserved.
• Palladium-Catalyzed Addition of Arylboronic Acids to Aldehydes
  作者：Tetsuya Yamamoto、Tetsuo Ohta、Yoshihiko Ito

  DOI：10.1021/ol051501y

  日期：2005.9.1

  Arylboronic acids react with aldehydes in the presence of a base and a catalytic amount of a palladium(0) complex with chloroform, affording the corresponding secondary alcohols in good yields. General palladium complexes have no catalytic activity without chloroform. Chloroform is essential for this reaction, and palladium complex that was prepared from Pd(PPh3)(4) with CHCl3 showed good catalytic acitivty as well.