1-(2,4,6-Trimethoxy-phenyl)-naphthalene | 594823-70-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 1-(2,4,6-Trimethoxy-phenyl)-naphthalene
• 英文别名: 1-(2,4,6-Trimethoxyphenyl)naphthalene；1-(2,4,6-trimethoxyphenyl)naphthalene
• CAS: 594823-70-8
• 化学式: C₁₉H₁₈O₃
• 分子量: 294.35
• InChiKey: CDQGXBWHDWXRLT-UHFFFAOYSA-N

物化性质

• 沸点：
  393.2±42.0 °C(Predicted)
• 密度：
  1.128±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.7
• 重原子数：
  22
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.16
• 拓扑面积：
  27.7
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  1-溴代萘 、 在 N-甲基吡咯烷酮 、 四(三苯基膦)钯 作用下， 反应 5.0h， 以87%的产率得到1-(2,4,6-Trimethoxy-phenyl)-naphthalene
  参考文献：
  名称：

  5,6,7,12-四氢二苯并[c，f] [1,5]氮杂双嘧啶：高反应性和可回收的有机铋试剂，用于与芳基溴化物的交叉偶联反应。

  摘要：

  DOI：

  10.1002/anie.200250205

文献信息

• Stable Au(I) catalysts for oxidant-free C-H functionalization with iodoarenes
  作者：R. Tyler Mertens、Charles E. Greif、James T. Coogle、Gilles Berger、Sean Parkin、Mark D. Watson、Samuel G. Awuah

  DOI：10.1016/j.jcat.2022.02.019

  日期：2022.4

  oxidant-free gold-catalyzed cross coupling reactions involving aryl halides have been hamstrung by the lack of gold catalysts capable of performing oxidative addition at Au(I) centers. Herein, we report the development of novel tricoordinate Au(I) catalysts supported by N,N-bidentate ligands and ligated by phosphine or arsine ligands for C-H functionalization without external oxidants to form biaryls

  由于缺乏能够在 Au(I) 中心进行氧化加成的金催化剂，涉及芳基卤化物的无氧化剂金催化交叉偶联反应的发展受到阻碍。在此，我们报道了新型三配位Au(I)催化剂的开发，该催化剂由N,N-二齿配体支撑，并通过膦或胂配体连接，在没有外部氧化剂的情况下进行CH官能化，形成无自偶联的联芳基。 Au(I) 催化剂的不对称特性对于促进这种必要的正交变换至关重要。这项研究揭示了 Au(I) 催化在联芳基合成中的另一个潜力。
• Synthesis of NHC Ligands Containing a Sulfoxide Moiety and Their Use in Cross-Coupling via a Au(I)/(III) Catalytic Cycle
  作者：Takanori Shibata、Rikako Nagai、Sari Okazaki、Shun Nishibe、Mamoru Ito

  DOI：10.1246/bcsj.20220013

  日期：2022.4.15

  We designed and synthesized a new series of NHCs with a sulfoxide moiety as a hemilabile ligand. We investigated the catalytic activities of Au(I)-NHC complexes in the strong oxidant-free cross-coupling of iodoarenes with 1,3,5-trimethoxybenzene. We ascertained that the sulfoxide moiety is critical for the Au(I)/(III) catalytic cycle.

  我们设计并合成了一系列新的以亚砜部分作为半可配体的 NHC。我们研究了 Au(I)-NHC 配合物在碘芳烃与 1,3,5-三甲氧基苯的无强氧化剂交叉偶联中的催化活性。我们确定亚砜部分对 Au(I)/(III) 催化循环至关重要。
• L‐Shaped Heterobidentate Imidazo[1,5‐ <i>a</i> ]pyridin‐3‐ylidene (N,C)‐Ligands for Oxidant‐Free Au ^I /Au ^III Catalysis
  作者：Pengcheng Gao、Jihong Xu、Tongliang Zhou、Yanhong Liu、Elwira Bisz、Błażej Dziuk、Roger Lalancette、Roman Szostak、Dongju Zhang、Michal Szostak

  DOI：10.1002/anie.202218427

  日期：2023.3.13

  AbstractIn the last decade, major advances have been made in homogeneous gold catalysis. However, AuI/AuIII catalytic cycle remains much less explored due to the reluctance of AuI to undergo oxidative addition and the stability of the AuIII intermediate. Herein, we report activation of aryl halides at gold(I) enabled by NHC (NHC=N‐heterocyclic carbene) ligands through the development of a new class of L‐shaped heterobidentate ImPy (ImPy=imidazo[1,5‐a]pyridin‐3‐ylidene) N,C ligands that feature hemilabile character of the amino group in combination with strong σ‐donation of the carbene center in a rigid conformation, imposed by the ligand architecture. Detailed characterization and control studies reveal key ligand features for AuI/AuIII redox cycle, wherein the hemilabile nitrogen is placed at the coordinating position of a rigid framework. Given the tremendous significance of homogeneous gold catalysis, we anticipate that this ligand platform will find widespread application.
• 5,6,7,12-Tetrahydrodibenz[c,f][1,5]azabismocines: Highly Reactive and Recoverable Organobismuth Reagents for Cross-Coupling Reactions with Aryl Bromides
  作者：Shigeru Shimada、Osamu Yamazaki、Toshifumi Tanaka、Maddali L. N. Rao、Yohichi Suzuki、Masato Tanaka

  DOI：10.1002/anie.200250205

  日期：2003.4.25