2-methoxy-4'-methyl-1,1'-binaphthyl

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 2-methoxy-4'-methyl-1,1'-binaphthyl
• 英文别名: (R_a)-2-methoxy-4'-methyl-1,1'-binaphthalene；(R)-2-methoxy-4'-methyl-1,1'-binaphthyl；(Ra)-2-methoxy-4'-methyl-1,1'-binaphthyl；1-(2-Methoxynaphthalen-1-yl)-4-methylnaphthalene；1-(2-methoxynaphthalen-1-yl)-4-methylnaphthalene
• 化学式: C₂₂H₁₈O
• 分子量: 298.384
• InChiKey: GMQSXDJXDRNBRV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.4
• 重原子数：
  23
• 可旋转键数：
  2
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.09
• 拓扑面积：
  9.2
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为产物：
  描述：

  1-溴-2-甲氧基萘 在 tris-(dibenzylideneacetone)dipalladium(0) 、 正丁基锂 、 2-二环己膦基-2'-(N,N-二甲胺)-联苯 作用下， 以 四氢呋喃 为溶剂， 生成 2-methoxy-4'-methyl-1,1'-binaphthyl
  参考文献：
  名称：

  钯催化三有机铟试剂交叉偶联反应合成轴向手性1,1'-联萘

  摘要：

  通过钯催化的三（1-萘基）铟试剂与 1-卤代萘和卤代异喹啉之间的交叉偶联反应，可以有效地制备 1,1'-联萘和杂环类似物。反应通常在 80 °C 的 THF 中进行，铟试剂略过量（40 mol%）和低催化剂负载（4 mol% Pd），以良好的产率提供交叉偶联产物（45 –99%）。该方法允许合成空间位阻的 2-取代和 2,2'-二取代 1,1'-联萘和萘基异喹啉。此外，偶联反应可以对映选择性进行，并通过使用手性氨基磷烷二茂铁基配体 (R,S)-PPFA 获得最佳对映体过量。

  DOI：

  10.1002/ejoc.201300042

文献信息

• An enantioselective artificial Suzukiase based on the biotin–streptavidin technology
  作者：Anamitra Chatterjee、Hendrik Mallin、Juliane Klehr、Jaicy Vallapurackal、Aaron D. Finke、Laura Vera、May Marsh、Thomas R. Ward

  DOI：10.1039/c5sc03116h

  日期：——

  Introduction of a biotinylated monophosphine palladium complex within streptavidin affords an enantioselective artificial Suzukiase. Site-directed mutagenesis allowed the optimization of the activity and the enantioselectivity of this artificial metalloenzyme. A variety of atropisomeric biaryls were produced in good yields and up to 90% ee.

  将生物素化的单磷酸钯配合物引入链霉亲合素中，形成对映选择性的人工银催化剂。通过位点定向突变优化了这种人工金属酶的活性和对映选择性。产率良好，对映纯度高达90%，产生了多种二苯基异构体。
• Fine Tuning of Chiral Bis(N-heterocyclic carbene) Palladium Catalysts for Asymmetric Suzuki–Miyaura Cross-Coupling Reactions: Exploring the Ligand Modification
  作者：Dao Zhang、Jueqin Yu

  DOI：10.1021/acs.organomet.0c00036

  日期：2020.4.27

  aryl–aryl cross-coupling reactions of arylboronic acids and aryl halides. The enantioselectivity of the biaryl products was greatly improved within 24 h (up to 74% ee) when complexes 7a–g were used as catalysts. The results show that for these types of bis(NHC) palladium catalysts the structural characters of the chiral scaffolds play a decisive role in the enantioselectivities of cross-coupling reactions

  新型手性Ñ，Ñ '-bisaryl双（NHC）配体前体ħ 2 [（小号） - 2 ]氯2上的螺支架和H 2 [（小号） -图3b -克]氯2与联萘联动被合理地设计合成了它们的环金属化的顺式螯合NHC钯配合物（S）-5，（S）-6和（S）-7b - g。配合物6和7bX射线单晶分析进一步证实了这一点。两种配合物均在Pd（II）中心周围采用了略微扭曲的正方形平面几何形状。6的结构由罕见的二聚体结构组成，其中包含通过短金属-金属键（2.853（2）Å）键合的两个钯（II）中心，表明Pd II –Pd II分子内相互作用（<3.00Å）。这些Ñ，Ñ '-bisaryl双（NHC）-Pd络合物连同Ñ，Ñ '-bisalkyl类似物[（小号） - 1A - ð ] PDX 2 }（X = I，（小号） -图4a ; X = BR，（小号）-4b – d）已用于芳基硼酸和芳基卤化物的不对称芳基-芳基交叉偶联反应。当配合物7a
• Atroposelective Arene‐Forming Alkene Metathesis**
  作者：Zlatko Jončev、Christof Sparr

  DOI：10.1002/anie.202211168

  日期：2022.12.19

  The feasibility of alkene metathesis to catalytically control stereogenic axes by traceless arene formation is reported. Key to the process is a selective conversion of stereodynamic trienes by a chiral molybdenum catalyst, providing configurationally-stable atropisomers under mild conditions in excellent yields with up to 98 : 2 e.r.

  报道了烯烃复分解通过无痕芳烃形成催化控制立体轴的可行性。该过程的关键是通过手性钼催化剂选择性转化立体动力学三烯，在温和条件下以高达 98 : 2 er 的优异收率提供构型稳定的阻转异构体
• 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.