1-(2-(dimethylamino)-5-methoxyphenyl)naphthalene-2-ol | 1346855-14-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 1-(2-(dimethylamino)-5-methoxyphenyl)naphthalene-2-ol
• 英文别名: 1-(2-(dimethylamino)-5-methoxyphenyl)naphthalen-2-ol；1-[2-(Dimethylamino)-5-methoxyphenyl]naphthalen-2-ol
• CAS: 1346855-14-8
• 化学式: C₁₉H₁₉NO₂
• 分子量: 293.365
• InChiKey: WOYSKEBMWZKSOY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.5
• 重原子数：
  22
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.16
• 拓扑面积：
  32.7
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  (4-甲氧基苯基)-二甲胺 、 2-萘酚 在 叔丁基过氧化氢 、 iron(III) chloride hexahydrate 作用下， 以 甲苯 为溶剂， 以60%的产率得到1-(2-(dimethylamino)-5-methoxyphenyl)naphthalene-2-ol
  参考文献：
  名称：

  铁催化的区域选择性直接氧化芳基-芳基交叉偶联

  摘要：

  据报道，在温和条件下，使用叔-BuOOH作为氧化剂的两种芳香族化合物的区域选择性铁催化的交叉脱氢偶联（CDC）。直接的氧化偶联反应对在基质功能基团邻位的碳-碳键产生选择性，从而完全阻止了均相偶联的产物。C–C键形成反应使该方法变得通用，从而导致功能化的2,2'-二取代联芳基。

  DOI：

  10.1021/jo202152b

文献信息

• Aerobic Catalyzed Oxidative Cross-Coupling of <i>N</i>,<i>N</i>-Disubstituted Anilines and Aminonaphthalenes with Phenols and Naphthols
  作者：Thomas J. Paniak、Marisa C. Kozlowski

  DOI：10.1021/acs.orglett.0c00046

  日期：2020.3.6

  N-dialkyl aniline and aminonaphthalenes with phenols and naphthols using a Cr-salen catalyst under aerobic conditions was developed. Notably, air serves as an effective oxidant affording products in high selectivity. Initial mechanistic studies suggest an outer-sphere oxidation of the aniline/aminonaphthalene partner, followed by nucleophilic attack of the phenol/naphthol. Single products were observed

  开发了在好氧条件下使用Cr-salen催化剂将N，N-二烷基苯胺和氨基萘与酚和萘交叉偶联的方法。值得注意的是，空气以有效的氧化剂提供了高选择性的产物。最初的机理研究表明，苯胺/氨基萘伴侣会发生外层氧化，然后苯酚/萘酚会发生亲核攻击。在大多数情况下，观察到单一产物，而CC和CO偶联产物的混合物是由涉及氨基萘和空间上不受阻碍的苯酚的反应产生的。
• Iron‐Catalyzed Oxidative C−C Cross‐Coupling Reaction of Tertiary Anilines with Hydroxyarenes by Using Air as Sole Oxidant
  作者：Alexander Purtsas、Olga Kataeva、Hans‐Joachim Knölker

  DOI：10.1002/chem.201905595

  日期：2020.2.21

  A mild procedure for the oxidative C-C cross-coupling of tertiary anilines with phenols is described which provides the products generally in high yields and with excellent selectivity. The reaction is catalyzed by the hexadecafluorinated iron-phthalocyanine complex FePcF16 in the presence of substoichiometric amounts of methanesulfonic acid and ambient air as sole oxidant.

  描述了用于叔苯胺与酚的氧化CC交叉偶联的温和方法，该方法通常以高收率和优异的选择性提供产物。在亚化学计量量的甲磺酸和环境空气作为唯一氧化剂存在下，通过十六氟化铁-酞菁配合物FePcF16催化该反应。
• Cerium-containing MCM-41 catalyst for selective oxidative arene cross-dehydrogenative coupling reactions
  作者：Adinarayana Murthy Akondi、Rajiv Trivedi、Bojja Sreedhar、Mannepalli Lakshmi Kantam、Suresh Bhargava

  DOI：10.1016/j.cattod.2012.05.029

  日期：2012.12

  Cerium (IV)-mediated intermolecular direct biaryl coupling of aromatic tertiary amines and naphthol via dual C-H bond activation has been reported. The new C-C bond is formed regioselectively ortho to the amino and hydroxyl substituents under oxidative conditions to give substituted bifunctional amino naphthols. We report here the use of Ce-MCM-41 catalyst for the synthesis of these unsymmetrical biaryls via oxidative cross coupling under mild conditions. The catalyst was recovered by simple filtration and reused for several cycles with consistent activity. (C) 2012 Elsevier B. V. All rights reserved.
• Iron-Catalyzed Regioselective Direct Oxidative Aryl–Aryl Cross-Coupling
  作者：Malapaka Chandrasekharam、Barreddi Chiranjeevi、Kankatala S. V. Gupta、B. Sridhar

  DOI：10.1021/jo202152b

  日期：2011.12.16

  Regioselective iron-catalyzed cross-dehydrogenative coupling (CDC) of two aromatic compounds using tert-BuOOH as oxidant under mild conditions has been reported. The direct oxidative coupling reaction is selective toward creation of a carbon–carbon bond at the position ortho to the functional groups of the substrates, completely preventing the homocoupled products. The C–C bond-forming reaction makes

  据报道，在温和条件下，使用叔-BuOOH作为氧化剂的两种芳香族化合物的区域选择性铁催化的交叉脱氢偶联（CDC）。直接的氧化偶联反应对在基质功能基团邻位的碳-碳键产生选择性，从而完全阻止了均相偶联的产物。C–C键形成反应使该方法变得通用，从而导致功能化的2,2'-二取代联芳基。