5-(benzo[d][1,3]dioxol-5-yl)-2-(naphthalen-2-yl)oxazole | 1352192-53-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 5-(benzo[d][1,3]dioxol-5-yl)-2-(naphthalen-2-yl)oxazole
• 英文别名: 5-(benzo[1,3]dioxol-5-yl)-2-(naphthalen-2-yl)oxazole；5-(1,3-Benzodioxol-5-yl)-2-naphthalen-2-yl-1,3-oxazole；5-(1,3-benzodioxol-5-yl)-2-naphthalen-2-yl-1,3-oxazole
• CAS: 1352192-53-0
• 化学式: C₂₀H₁₃NO₃
• 分子量: 315.328
• InChiKey: GEIORARHHNDECD-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.7
• 重原子数：
  24
• 可旋转键数：
  2
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.05
• 拓扑面积：
  44.5
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  2-naphthyl pivalate 、 5-(benzo[d][1,3]dioxol-5-yl)oxazole 在 bis(1,5-cyclooctadiene)nickel (0) 、 caesium carbonate 、 1,2-双(二环己基磷基)-乙烷 作用下， 以 1,4-二氧六环 为溶剂， 反应 12.0h， 以72%的产率得到5-(benzo[d][1,3]dioxol-5-yl)-2-(naphthalen-2-yl)oxazole
  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

• 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.