ethyl 3-(4-(dimethylamino)phenyl)-1H-pyrazole-5-carboxylate | 1537177-53-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: ethyl 3-(4-(dimethylamino)phenyl)-1H-pyrazole-5-carboxylate
• 英文别名: ethyl 3-[4-(dimethylamino)phenyl]-1H-pyrazole-5-carboxylate
• CAS: 1537177-53-9
• 化学式: C₁₄H₁₇N₃O₂
• 分子量: 259.308
• InChiKey: BXNPNOKADWGTPU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  19
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  58.2
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  ethyl 2-acetoxy-4-(4-(dimethylamino)phenyl)-3-nitrobut-3-enoate 、 对甲苯磺酰肼 在 sodium carbonate 作用下， 以 甲醇 为溶剂， 反应 2.0h， 以72%的产率得到ethyl 3-(4-(dimethylamino)phenyl)-1H-pyrazole-5-carboxylate
  参考文献：
  名称：

  Cascade regioselective synthesis of pyrazoles from nitroallylic acetates and N-tosyl hydrazine

  摘要：

  A simple, practical, and regioselective synthetic protocol for the formation of pyrazoles was developed. Unlike all other previously reported reactions of nitroallylic acetates, this process was initiated by a S(N)2 reaction at the electrophilic gamma site. A plausible mechanism for the cascade S(N)2-Michael synthesis is proposed. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2013.12.046

文献信息

• Cascade regioselective synthesis of pyrazoles from nitroallylic acetates and N-tosyl hydrazine
  作者：Nana Shao、Tong Chen、Taotao Zhang、Huajian Zhu、Qunxiong Zheng、Hongbin Zou

  DOI：10.1016/j.tet.2013.12.046

  日期：2014.1

  A simple, practical, and regioselective synthetic protocol for the formation of pyrazoles was developed. Unlike all other previously reported reactions of nitroallylic acetates, this process was initiated by a S(N)2 reaction at the electrophilic gamma site. A plausible mechanism for the cascade S(N)2-Michael synthesis is proposed. (C) 2013 Elsevier Ltd. All rights reserved.