1-(2-iodopyridin-3-ylmethyl)pyrrole-2-carboxylic acid methoxy methyl amide | 902147-07-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯
• 英文名称: 1-(2-iodopyridin-3-ylmethyl)pyrrole-2-carboxylic acid methoxy methyl amide
• 英文别名: 1-[(2-iodopyridin-3-yl)methyl]-N-methoxy-N-methylpyrrole-2-carboxamide
• CAS: 902147-07-3
• 化学式: C₁₃H₁₄IN₃O₂
• 分子量: 371.178
• InChiKey: XLOQVJJLCQGUIZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  19
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.23
• 拓扑面积：
  47.4
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  1-(2-iodopyridin-3-ylmethyl)pyrrole-2-carboxylic acid methoxy methyl amide 在 正丁基锂 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 反应 0.08h， 以85%的产率得到
  参考文献：
  名称：

  Intramolecular cyclisation of functionalised heteroaryllithiums. Synthesis of novel indolizinone-based compounds

  摘要：

  The intramolecular cyclisation of heteroaryllithiums derived from N-heteroarylmethylpyrrole-2-carboxam ides takes place smoothly at low temperature when N-methoxy-N-methyl and morpholine amides are used as internal electrophiles. Halogen-lithium exchange using n-BuLi is the method of choice to achieve metalation on the quinoline and pyridine derivatives, while directed lithiation (LDA) works better for furan. In the case of thiophene both methodologies can be applied. These metalation-cyclisation sequences provide a useful entry to several types of indolizidine based compounds (pyrrolo[1,2-b]acridinones, pyrrolo[1,2-g]quinolones, thieno and furo[3,2-f]indolizinones). (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2006.04.057
• 作为产物：
  描述：

  2-溴-3-吡啶甲醛 在 氢氧化钾 、 sodium tetrahydroborate 、 copper(l) iodide 、 sodium iodide 、 N,N'-二甲基乙二胺 作用下， 以 1,4-二氧六环 、 二甲基亚砜 为溶剂， 反应 19.0h， 生成 1-(2-iodopyridin-3-ylmethyl)pyrrole-2-carboxylic acid methoxy methyl amide
  参考文献：
  名称：

  Intramolecular cyclisation of functionalised heteroaryllithiums. Synthesis of novel indolizinone-based compounds

  摘要：

  The intramolecular cyclisation of heteroaryllithiums derived from N-heteroarylmethylpyrrole-2-carboxam ides takes place smoothly at low temperature when N-methoxy-N-methyl and morpholine amides are used as internal electrophiles. Halogen-lithium exchange using n-BuLi is the method of choice to achieve metalation on the quinoline and pyridine derivatives, while directed lithiation (LDA) works better for furan. In the case of thiophene both methodologies can be applied. These metalation-cyclisation sequences provide a useful entry to several types of indolizidine based compounds (pyrrolo[1,2-b]acridinones, pyrrolo[1,2-g]quinolones, thieno and furo[3,2-f]indolizinones). (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2006.04.057