6-methyl-2-(2-naphthyl)benzo[d]oxazole

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 6-methyl-2-(2-naphthyl)benzo[d]oxazole
• 英文别名: 6-methyl-2-(naphthalen-2-yl)benzoxazole；6-Methyl-2-(2-naphthyl)-1,3-benzoxazole；6-methyl-2-naphthalen-2-yl-1,3-benzoxazole
• 化学式: C₁₈H₁₃NO
• 分子量: 259.307
• InChiKey: DTZPSQFPEWIWRH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5
• 重原子数：
  20
• 可旋转键数：
  1
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.06
• 拓扑面积：
  26
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  N-(2-溴-4-甲基苯基)-2-萘酰胺 在 四甲基乙二胺 、 copper(II) bis(trifluoromethanesulfonate) 作用下， 以 水 为溶剂， 以65%的产率得到6-methyl-2-(2-naphthyl)benzo[d]oxazole
  参考文献：
  名称：

  Copper-catalysed intramolecular O-arylation of aryl chlorides and bromides: a straightforward approach to benzo[d]oxazoles in water

  摘要：

  A general, efficient and more sustainable protocol for the copper-catalysed intramolecular O-arylation of o'- haloanilides leading to the benzo[d]oxazole core is reported. Remarkably, the optimised conditions allowed for the use of inexpensive and easily available aryl chlorides as arylating agents. Moreover, all reactions were carried out employing exclusively water as the solvent, rendering the methodology presented herein highly valuable from both environmental and economic points of view. (c) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2007.08.013

文献信息

• Coupling of Heteroarene and Arenol via Nickel‐Catalyzed C−H/C−OH Activation
  作者：Chen‐Hsun Hung、Ting‐Hsuan Wang、Glenn P. A. Yap、Joon Ching Juan、Tiow‐Gan Ong

  DOI：10.1002/cctc.202300249

  日期：2023.6.9

  A nickel-catalyzed heteroarene C−H/arenol C−OH coupling reaction is reported, which omits the use of strong Lewis-acid additive and low atom-economy protecting reagent. Arrays of arenols and heteroarenes are effective in this protocol using the in-situ activating reagent pivalic anhydride.

  报道了镍催化的杂芳烃 C-H/芳醇 C-OH 偶联反应，该反应省略了强路易斯酸添加剂和低原子经济性保护试剂的使用。arenols 和 heteroarenes 的阵列在该协议中使用原位激活试剂 pivalic 酸酐是有效的。
• Nickel-Catalyzed C–H/C–O Coupling of Azoles with Phenol Derivatives
  作者：Kei Muto、Junichiro Yamaguchi、Kenichiro Itami

  DOI：10.1021/ja210249h

  日期：2012.1.11

  The first nickel-catalyzed C-H bond arylation of azoles with phenol derivatives is described. The new Ni(cod)(2)/dcype catalytic system is active for the coupling of various phenol derivatives such as esters, carbamates, carbonates, sulfamates, triflates, tosylates, and mesylates. With this C-H/C-O biaryl coupling, we synthesized a series of privileged 2-arylazoles, including biologically active alkaloids. Moreover, we demonstrated the utility of the present reaction for functionalizing estrone and quinine.
• METHOD FOR PRODUCING PHENYL-SUBSTITUTED HETEROCYCLIC DERIVATIVE
  申请人：National University Corporation Nagoya University

  公开号：EP2774923B1

  公开（公告）日：2016-05-18
• US20140275549A1
  申请人：——

  公开号：US20140275549A1

  公开（公告）日：2014-09-18
• US8993777B2
  申请人：——

  公开号：US8993777B2

  公开（公告）日：2015-03-31