(5,6-dihydro-4H-pyrrolo[1,2-b]pyrazol-3-yl)methanamine | 1260672-10-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯并吡唑类
• 英文名称: (5,6-dihydro-4H-pyrrolo[1,2-b]pyrazol-3-yl)methanamine
• 英文别名: (5,6-Dihydro-4H-pyrrolo[1,2-b]pyrazol-3-yl)methanamine；5,6-dihydro-4H-pyrrolo[1,2-b]pyrazol-3-ylmethanamine
• CAS: 1260672-10-3
• 化学式: C₇H₁₁N₃
• 分子量: 137.184
• InChiKey: YBQHCOCESJJECE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.5
• 重原子数：
  10
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.57
• 拓扑面积：
  43.8
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  5,6-二氢-4H-吡咯并[1,2-b]吡唑 在 ammonium hydroxide 、 N-溴代丁二酰亚胺(NBS) 、 正丁基锂 、 盐酸羟胺 、 氢气 、 sodium carbonate 作用下， 以 四氢呋喃 、 甲醇 、 乙醇 、 正己烷 、 N,N-二甲基甲酰胺 为溶剂， -78.0~20.0 ℃ 、137.9 kPa 条件下， 反应 1.5h， 生成 (5,6-dihydro-4H-pyrrolo[1,2-b]pyrazol-3-yl)methanamine
  参考文献：
  名称：

  Synthesis of (5,6-Dihydro-4H-pyrrolo[1,2-b]pyrazol-3-yl)-methanamine

  摘要：

  This short paper reports the development of a new method for the synthesis of (5,6-dihydro-4H-pyrrolo[1,2-b]pyrazol-3-yl)methanamine. Pyrazole was initially protected with an N-SEM protective group, followed by alkylation at C-5 position with 1-bromo-3-chloropropane. Following SEM deprotection, the intramolecular ring was closed and then a bromine atom (Br) was introduced with N-bromosuccinimide (NBS) by electrophilic aromatic substitution (SEAr), forming 3-bromo-5,6-dihydro-4H-pyrrolo[1,2-b]pyrazole. The Br group was subsequently converted into aldehyde group, then into oxime. The final step of hydrogenation resulted in the desired product. The overall yield through the 8-step reaction process was found to be 29.4%. The intermediates and final product were identified by HPLC-MS and H-1 NMR. This development provides a novel synthetic route to the formation of 5,6-dihydro-4H-pyrrolo[1,2-b]pyrazole skeleton.

  DOI：

  10.3987/com-17-13772

文献信息

• Synthesis of (5,6-Dihydro-4H-pyrrolo[1,2-b]pyrazol-3-yl)-methanamine
  作者：Xun-Li Zhang、Yu Ma、Qing Pan、Zhong-Gang Bai、Hui Qi、Qun-Zheng Zhang

  DOI：10.3987/com-17-13772

  日期：——

  This short paper reports the development of a new method for the synthesis of (5,6-dihydro-4H-pyrrolo[1,2-b]pyrazol-3-yl)methanamine. Pyrazole was initially protected with an N-SEM protective group, followed by alkylation at C-5 position with 1-bromo-3-chloropropane. Following SEM deprotection, the intramolecular ring was closed and then a bromine atom (Br) was introduced with N-bromosuccinimide (NBS) by electrophilic aromatic substitution (SEAr), forming 3-bromo-5,6-dihydro-4H-pyrrolo[1,2-b]pyrazole. The Br group was subsequently converted into aldehyde group, then into oxime. The final step of hydrogenation resulted in the desired product. The overall yield through the 8-step reaction process was found to be 29.4%. The intermediates and final product were identified by HPLC-MS and H-1 NMR. This development provides a novel synthetic route to the formation of 5,6-dihydro-4H-pyrrolo[1,2-b]pyrazole skeleton.