(benzoxazol-2-yl)(6-chloropyridin-3-yl)methanone | 1426082-91-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并恶唑类
• 英文名称: (benzoxazol-2-yl)(6-chloropyridin-3-yl)methanone
• 英文别名: 1,3-Benzoxazol-2-yl-(6-chloropyridin-3-yl)methanone；1,3-benzoxazol-2-yl-(6-chloropyridin-3-yl)methanone
• CAS: 1426082-91-8
• 化学式: C₁₃H₇ClN₂O₂
• 分子量: 258.664
• InChiKey: PAYBVKBMEXJLHL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  18
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  56
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (benzoxazol-2-yl)(6-chloropyridin-3-yl)methanone 在 盐酸 、 titanium(IV) tetraethanolate 作用下， 以 四氢呋喃 、 1,4-二氧六环 、 甲醇 为溶剂， 反应 11.08h， 生成 (R)-(+)-1-(benzoxazol-2-yl)-1-(6-chloropyridin-3-yl)ethylammonium chloride
  参考文献：
  名称：

  Organocatalytic C–H Bond Arylation of Aldehydes to Bis-heteroaryl Ketones

  摘要：

  An organocatalytic aldehyde C-H bond arylation process for the synthesis of complex heteroaryl ketones has been developed. By exploiting the inherent electrophilicity of diaryliodonium salts, we have found that a commercial N-heterocyclic carbene catalyst promotes the union of heteroaryl aldehydes and these heteroaromatic electrophile equivalents in good yields. This straightforward catalytic protocol offers access to ketones bearing a diverse array of arene and heteroarene substituents that can subsequently be converted into molecules displaying structural motifs commonly found in medicinal agents.

  DOI：

  10.1021/ja400051d
• 作为产物：
  描述：

  2-氯-5-碘吡啶 在 2-pentafluorophenyl-6,7-dihydro-5H-pyrrolo[2,1-c][1,2,4]triazol-2-ium tetrafluoroborate 、 4-二甲氨基吡啶 、 水 、 间氯过氧苯甲酸 作用下， 以 二氯甲烷 为溶剂， 反应 25.0h， 生成 (benzoxazol-2-yl)(6-chloropyridin-3-yl)methanone
  参考文献：
  名称：

  Organocatalytic C–H Bond Arylation of Aldehydes to Bis-heteroaryl Ketones

  摘要：

  An organocatalytic aldehyde C-H bond arylation process for the synthesis of complex heteroaryl ketones has been developed. By exploiting the inherent electrophilicity of diaryliodonium salts, we have found that a commercial N-heterocyclic carbene catalyst promotes the union of heteroaryl aldehydes and these heteroaromatic electrophile equivalents in good yields. This straightforward catalytic protocol offers access to ketones bearing a diverse array of arene and heteroarene substituents that can subsequently be converted into molecules displaying structural motifs commonly found in medicinal agents.

  DOI：

  10.1021/ja400051d

文献信息

• Organocatalytic C–H Bond Arylation of Aldehydes to Bis-heteroaryl Ketones
  作者：Qiao Yan Toh、Andrew McNally、Silvia Vera、Nico Erdmann、Matthew J. Gaunt

  DOI：10.1021/ja400051d

  日期：2013.3.13

  An organocatalytic aldehyde C-H bond arylation process for the synthesis of complex heteroaryl ketones has been developed. By exploiting the inherent electrophilicity of diaryliodonium salts, we have found that a commercial N-heterocyclic carbene catalyst promotes the union of heteroaryl aldehydes and these heteroaromatic electrophile equivalents in good yields. This straightforward catalytic protocol offers access to ketones bearing a diverse array of arene and heteroarene substituents that can subsequently be converted into molecules displaying structural motifs commonly found in medicinal agents.