1-(4-nitrobenzyl)octahydro-[1,3,2]diazaphospholo[1,5-a]pyridine-1-oxide

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 1-(4-nitrobenzyl)octahydro-[1,3,2]diazaphospholo[1,5-a]pyridine-1-oxide
• 英文别名: 1-[(4-nitrophenyl)methyl]-3,3a,4,5,6,7-hexahydro-2H-[1,3,2]diazaphospholo[1,5-a]pyridine 1-oxide
• 化学式: C₁₃H₁₈N₃O₃P
• 分子量: 295.278
• InChiKey: XIYSNDMCYFYKPJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  20
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.54
• 拓扑面积：
  78.2
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  2-氨甲基哌啶 在 cerium(III) chloride heptahydrate 、 三乙胺 、 三氯化磷 作用下， 以 四氢呋喃 为溶剂， 反应 7.25h， 生成 1-(4-nitrobenzyl)octahydro-[1,3,2]diazaphospholo[1,5-a]pyridine-1-oxide
  参考文献：
  名称：

  CeCl3·7H2O: a highly efficient catalyst for the synthesis of 1-substituted-octahydro-[1,3,2]diazaphospholo[1,5-a]pyridine-1-oxide

  摘要：

  An efficient and simple protocol is reported for the synthesis of a new class of 1-substituted-octahydro[1,3,2]diazaphospholo[1,5-a]pyridine-1-oxides in good to excellent yield (88-95%) via Michaelis Arbuzov rearrangement. Condensation of diamido phosphite with various halides at 60 degrees C using CeCl3 center dot 7H(2)O as a highly efficient catalyst afforded the products within a short period of reaction time. This procedure is mild, efficient, and non-toxic and stability of the catalyst is the merit of this process. Therefore, this protocol being environmentally benign and efficient, serves as an alternative procedure for the preparation of the title compounds. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2013.08.115

文献信息

• CeCl3·7H2O: a highly efficient catalyst for the synthesis of 1-substituted-octahydro-[1,3,2]diazaphospholo[1,5-a]pyridine-1-oxide
  作者：Radha Rani Chinthaparthi、Chandra Sekhar Reddy Gangireddy、Veeranarayana Reddy Mudumala、Mohan Gundluru、Nagaraju Chamarthi、Suresh Reddy Cirandur

  DOI：10.1016/j.tetlet.2013.08.115

  日期：2013.11

  An efficient and simple protocol is reported for the synthesis of a new class of 1-substituted-octahydro[1,3,2]diazaphospholo[1,5-a]pyridine-1-oxides in good to excellent yield (88-95%) via Michaelis Arbuzov rearrangement. Condensation of diamido phosphite with various halides at 60 degrees C using CeCl3 center dot 7H(2)O as a highly efficient catalyst afforded the products within a short period of reaction time. This procedure is mild, efficient, and non-toxic and stability of the catalyst is the merit of this process. Therefore, this protocol being environmentally benign and efficient, serves as an alternative procedure for the preparation of the title compounds. (C) 2013 Elsevier Ltd. All rights reserved.