methyl 5-methyl-2-(naphthalen-2-yl)oxazole-4-carboxylate | 1352192-60-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: methyl 5-methyl-2-(naphthalen-2-yl)oxazole-4-carboxylate
• 英文别名: methyl-5-methyl-2-(naphthalen-2-yl)oxazole-4-carboxylate；Methyl 5-methyl-2-(naphthalen-2-yl)oxazole-4-carboxylate；methyl 5-methyl-2-naphthalen-2-yl-1,3-oxazole-4-carboxylate
• CAS: 1352192-60-9
• 化学式: C₁₆H₁₃NO₃
• 分子量: 267.284
• InChiKey: VNBAAUVZTBUILZ-UHFFFAOYSA-N

物化性质

• 沸点：
  431.6±37.0 °C(Predicted)
• 密度：
  1.220±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  20
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  52.3
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  2-naphthyl pivalate 、 5-甲基恶唑-4-甲酸甲酯 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methyl 5-methyl-2-(naphthalen-2-yl)oxazole-4-carboxylate
  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.