2-methoxy-1-(2-methoxyphenyl)naphthalene

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 2-methoxy-1-(2-methoxyphenyl)naphthalene
• 英文别名: 2-Methoxy-1-(2-methoxyphenyl)naphthalene
• 化学式: C₁₈H₁₆O₂
• 分子量: 264.324
• InChiKey: IJPOXOFMAUCNPZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.7
• 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：
  18.5
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  2-methoxynaphtyl(triphenylphosphine) gold(I) 、 2-methoxyphenyldiazonium tetrafluoroborate 在 tris(2,2-bipyridine)ruthenium(II) hexafluorophosphate 作用下， 以 乙腈 为溶剂， 反应 3.0h， 以65%的产率得到2-methoxy-1-(2-methoxyphenyl)naphthalene
  参考文献：
  名称：

  使用（P，N）金络合物对Au催化的芳基重氮盐与芳基硼酸之间交叉偶联的机理和不对称机理的研究†

  摘要：

  为了探索在CsF存在下AuN催化的ArN 2 BF 4和ArB（OH）2的交叉偶联中可能发生的不同机理，对具有（P，N）配体的金配合物进行了各种化学计量的实验。使用2-吡啶基苯基-二苯基膦使我们可以提出三种不同的机理途径，要么是通过两个连续的单电子转移进行的金属过渡步骤，要么暗示了Au（I）和Au（III）之间的金属过渡。） 物种。此外，当使用可商购的手性（P，N）配体时，ee最高可达26％，可以由合适的芳基重氮盐和芳基硼酸不对称地形成阻转异构联芳基。

  DOI：

  10.1039/c8cc07530a

文献信息

• Reactivity of Planar‐Chiral α‐Ferrocenyl Carbocations towards Electron‐Rich Aromatics
  作者：Marcus Korb、Julia Mahrholdt、Xianming Liu、Heinrich Lang

  DOI：10.1002/ejic.201801430

  日期：2019.2.21

  atropselective C,C cross‐coupling reactions for the synthesis of sterically hindered biaryls, where sandwich compound (Sp)‐1‐(PPh2)‐2‐(o‐NMe2‐C6H4)CH2‐Fc gave an ee of 69 % (1 mol‐% [Pd]), which is up to date the highest observed value for planar‐chiral ferrocenes. The absolute configuration of the chiral ferrocenes was confirmed by single‐crystal X‐ray diffraction analysis. For seleno phosphane 1‐(P(=Se)Ph2)‐2‐(CH2OH)‐Fc

  的对映体纯的，平面手性α-二茂铁基碳阳离子（的反应小号p）-2-（P（= S）PH 2）FCCH 2 +（FC =铁（η 5 -C 5 H ^ 5）（η 5 -C 5 H 3））朝着富电子芳烃C 6 H 5 E（E = NH 2，NMe 2，N i Pr 2，NPh 2，PPh 2，P（= S）Ph 2，OH，SH，SMe） E基团的亲核攻击或芳烃在CH处的亲电芳香取代反应报告2 +单位。发现氨基，氧代或硫代官能团在各种产品分布中赋予了相应的二茂铁，而基于P的物种则没有。可以将适当的硫代膦衍生物还原为它们的P III物种，这些化合物用作在阻转性C，C交叉偶联反应中用作支持位配体，以合成位阻联芳基，其中夹心化合物（S p）-1-（PPh 2）-2 -（o -NMe 2 -C 6 H 4）CH 2 -Fc给出了ee为69％（1 mol％[Pd]），这是迄今为止对平面手性二茂铁的最高观测值。手性
• Enantioselective Synthesis of Biaryl Compounds via Suzuki–Miyaura Cross-Coupling Using a Palladium Complex of 7′-Butoxy-7-(diphenylphosphino)-8,8′-biquinolyl: Investigation of a New Chiral Ligand Architecture
  作者：Paul Blakemore、Zhenhua Wu、Chao Wang、Lev Zakharov

  DOI：10.1055/s-0033-1340519

  日期：——

  effective for the synthesis of hindered 2,2′-disubstituted 1,1′-binaphthyls (78–83% yield, 20–38% ee). 7,7′-Dihydroxy-8,8′-biquinolyl was converted to the title phosphine in four-steps via Mitsunobu monoetherification, trifylation, phosphination, and phosphine oxide reduction (63% overall yield). Enantiomerically pure phosphine was combined with Pd2dba3 and investigated for the synthesis of axially chiral

  摘要 通过Mitsunobu单醚化，玻璃化，磷酸化和氧化膦还原反应，将7,7'-二羟基-8,8'-联喹啉基通过四个步骤转化为标题膦（总收率63％）。将对映体纯的膦与Pd 2 dba 3结合，并研究在K 3 PO 4存在下由Ar 1 Br和Ar 2 B（OH）2合成轴向手性联芳基化合物在甲苯溶剂中溶解（6个实例，产率4–97％，ee 4–74％）。为了比较目的，研究了类似的碳环配体2-（二苯基膦基）-2'-甲氧基-1,1'-联萘基（MOP），发现该化合物对合成受阻的2,2'-二取代的1,1'-有效双萘基（收率78-83％，ee 20-38％）。 通过Mitsunobu单醚化，玻璃化，磷酸化和氧化膦还原反应，将7,7'-二羟基-8,8'-联喹啉基通过四个步骤转化为标题膦（总收率63％）。将对映体纯的膦与Pd 2 dba 3结合，并研究在K 3 PO 4存在下由Ar 1 Br和Ar 2 B（OH
• Highly sterically hindered binaphthalene-based monophosphane ligands: synthesis and application in stereoselective Suzuki–Miyaura reactions
  作者：Michaela Mešková、Martin Putala

  DOI：10.1016/j.tetasy.2013.06.007

  日期：2013.8

  A series of new sterically hindered (R)-(2′-aryl-1,1′-binaphthalene-2-yl)phosphanes with ortho-substituted phenyls as aryl groups were prepared via Negishi monoarylation of enantiopure 2,2′-dibromo-1,1′-binaphthalene followed by lithiation and quenching with diphenylphosphanyl or dicyclohexylphosphanyl chloride. These ligands were applied to the stereoselective Suzuki–Miyaura coupling for the preparation

  一系列带有邻位的新的位阻（R）-（2'-芳基-1,1'-联萘-2-基）膦通过对映纯的2,2'-二溴-1,1'-联萘的Negishi单芳基化，然后锂化并用二苯基膦酰基或二环己基膦酰基氯淬灭，制备作为芳基的取代的苯基。这些配体被用于立体选择性的Suzuki-Miyaura偶联反应，以制备取代的联芳基。当增加配体的2'-芳基的阻碍时，对映选择性正相关。使用具有2,6-二甲氧基苯基芳基的性能最好的二苯基膦配体，可以以高至优异的收率（68–99％）和低至良好的ee（12–75％ee）制备各种芳基萘，后者可与使用其他手性单膦配体时报告的最佳值。
• Pd(II) complexes of monodentate deoxycholic acid derived binaphthyl diamido phosphites as chiral catalysts in the asymmetric Suzuki-Miyaura cross-coupling
  作者：Grazia Iannucci、Vincenzo Passarelli、Alessandro Passera、Anna Iuliano

  DOI：10.1016/j.tetasy.2017.09.012

  日期：2017.11

  Chiral binaphthyl diamidophosphites derived from deoxycholic acid were synthesized and used as ligands for the preparation of mononuclear Pd(II) complexes, which were employed as catalysts in the asymmetric Suzuki-Miyaura cross-coupling of arylboronic acids with aryl bromides. Among the different reaction parameters, the substrate concentration emerged as being crucial for the outcome of the reaction: the reaction was faster in a concentrated reaction mixture, and could be performed at 0 degrees C, where the reaction promoted by the Pd-complexes was more enantioselective affording cross-coupling products with ee up to 70%. (C) 2017 Elsevier Ltd. All rights reserved.
• Deoxycholic acid derived monophosphites as chiral ligands in the asymmetric Suzuki–Miyaura cross-coupling
  作者：Varsha R. Jumde、Anna Iuliano

  DOI：10.1016/j.tetasy.2011.12.006

  日期：2011.12

  Biaryl phosphites derived from deoxycholic acid were used as chiral ligands in the asymmetric Suzuki-Miyaura cross-coupling of arylboronic acids with aryl bromides. Amongst the different reaction parameters, the role of the base emerged as being crucial for the outcome of the reaction: the choice of base, and its amount, allowed enantiomerically enriched biaryl derivatives to be obtained at 1% catalyst loading and with an L:Pd ratio of 1:1. (C) 2011 Elsevier Ltd. All rights reserved.