2-(6-cyanonaphthalen-2-yl)benzoxazole | 1352192-44-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 2-(6-cyanonaphthalen-2-yl)benzoxazole
• 英文别名: 6-(1,3-Benzoxazol-2-yl)naphthalene-2-carbonitrile；6-(1,3-benzoxazol-2-yl)naphthalene-2-carbonitrile
• CAS: 1352192-44-9
• 化学式: C₁₈H₁₀N₂O
• 分子量: 270.29
• InChiKey: WPJYSVKUHYZBAF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.4
• 重原子数：
  21
• 可旋转键数：
  1
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  49.8
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  6-氰基-2-萘酚 在 4-二甲氨基吡啶 、 bis(1,5-cyclooctadiene)nickel (0) 、 caesium carbonate 、 三乙胺 、 1,2-双(二环己基磷基)-乙烷 作用下， 以 1,4-二氧六环 、 二氯甲烷 为溶剂， 反应 12.3h， 生成 2-(6-cyanonaphthalen-2-yl)benzoxazole
  参考文献：
  名称：

  Nickel-Catalyzed C–H/C–O Coupling of Azoles with Phenol Derivatives

  摘要：

  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.

  DOI：

  10.1021/ja210249h

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。
• 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
• 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.