methyl 2-pentyl-1,3-benzoxazole-6-carboxylate

• 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: methyl 2-pentyl-1,3-benzoxazole-6-carboxylate
• 英文别名: 6-carbomethoxy-2-pentylbenzoxazole
• 化学式: C₁₄H₁₇NO₃
• 分子量: 247.294
• InChiKey: UBYJLUSPBDDDLH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  18
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.43
• 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：

  3-羟基-4-硝基苯甲酸甲酯 、 正己醛 在 chromium dichloride 、 锰 、 三甲基氯硅烷 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 18.25h， 以55%的产率得到methyl 2-pentyl-1,3-benzoxazole-6-carboxylate
  参考文献：
  名称：

  Extending the Scope of Chromium−Manganese Redox-Coupled Reactions:  A One-Pot Synthesis of Benzoxazoles

  摘要：

  A critically important strategy for synthetic chemistry is the development of "domino" processes: those capable of concatenating multiple transformations into a single step. Such transformations not only provide an increase in synthetic efficiency, but also imply the development of a significant degree of mechanistic understanding. We report herein a new domino reaction, in which a chromium-manganese redox couple is employed both to catalytically reduce an o-hydroxy nitroarene and to oxidatively cyclize a subsequently formed imine. We find that the reaction is most effective for starting o-hydroxy nitroarenes with a strongly electron-withdrawing group at the para position.

  DOI：

  10.1021/jo005758f

文献信息

• Extending the Scope of Chromium−Manganese Redox-Coupled Reactions:  A One-Pot Synthesis of Benzoxazoles
  作者：Anitha Hari、Charles Karan、Warren C. Rodrigues、Benjamin L. Miller

  DOI：10.1021/jo005758f

  日期：2001.2.1

  A critically important strategy for synthetic chemistry is the development of "domino" processes: those capable of concatenating multiple transformations into a single step. Such transformations not only provide an increase in synthetic efficiency, but also imply the development of a significant degree of mechanistic understanding. We report herein a new domino reaction, in which a chromium-manganese redox couple is employed both to catalytically reduce an o-hydroxy nitroarene and to oxidatively cyclize a subsequently formed imine. We find that the reaction is most effective for starting o-hydroxy nitroarenes with a strongly electron-withdrawing group at the para position.
• Chikhale, Rupesh V.; Pant, Amit M.; Menghani, Sunil S., South African Journal of Chemistry, 2013, vol. 66, p. 254 - 262
  作者：Chikhale, Rupesh V.、Pant, Amit M.、Menghani, Sunil S.、Wadibhasme, Pankaj G.、Khedekar, Pramod B.

  DOI：——

  日期：——