3-iodo-1,6-dimethyl-4-phenyl-1-azaspiro [4.5]deca-3,6,9-triene-2,8-dione | 1364232-13-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯啉
• 英文名称: 3-iodo-1,6-dimethyl-4-phenyl-1-azaspiro [4.5]deca-3,6,9-triene-2,8-dione
• 英文别名: 3-Iodo-1,6-dimethyl-4-phenyl-1-azaspiro[4.5]deca-3,6,9-triene-2,8-dione
• CAS: 1364232-13-2
• 化学式: C₁₇H₁₄INO₂
• 分子量: 391.208
• InChiKey: UDMXHRZZWYVLPD-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  21
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  37.4
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  N-(4-methoxy-2-methylphenyl)-N-methyl-3-phenylpropiolamide 在 lithium perchlorate 、 lithium iodide 作用下， 以 乙腈 为溶剂， 反应 2.0h， 以86%的产率得到3-iodo-1,6-dimethyl-4-phenyl-1-azaspiro [4.5]deca-3,6,9-triene-2,8-dione
  参考文献：
  名称：

  N-芳基烷基酰胺的电化学氧化卤代反应合成螺[4.5]三烯酮

  摘要：

  我们开发了一种通过N-芳基炔酰胺的电化学氧化卤代环化合成螺[4.5]三烯酮的绿色方法。该反应在室温下在无金属催化剂和无外源氧化剂的条件下进行。使用现成的LiCl，LiBr和LiI作为卤素源，可以得到具有良好收率或优异收率的多种脱芳族卤代-螺环化产品，并具有广泛的范围和官能团耐受性。

  DOI：

  10.1021/acs.joc.0c02429

文献信息

• Metal‐Free ipso‐Halocyclization of N‐Arylpropynamides Using Hypervalent Iodine(III) Reagents under Aqueous Condition
  作者：Pankaj Jangir、Kalu Ram Bajya、Akshay S. Pathare、Mohammad Sodoor、Rinku Saini、Mukesh Purohit、Sermadurai Selvakumar

  DOI：10.1002/ejoc.202400203

  日期：2024.5.27

  An efficient intramolecular ipso-halocyclization of para-unsubstituted N-arylpropynamides proceeds using readily available hypervalent iodine reagents as oxidant and potassium halides as halogen source under aqueous medium. This method shows a broad substrate scope and doesn't require any metal catalysts.

  使用容易获得的高价碘试剂作为氧化剂和卤化钾作为卤素源，在水性介质下对未取代的N-芳基丙酰胺进行有效的分子内卤环化。该方法显示了广泛的底物范围并且不需要任何金属催化剂。
• Intramolecular <i>ipso</i>-Halocyclization of 4-(<i>p</i>-Unsubstituted-aryl)-1-alkynes Leading to Spiro[4,5]trienones: Scope, Application, and Mechanistic Investigations
  作者：Bo-Xiao Tang、Yue-Hua Zhang、Ren-Jie Song、Dong-Jun Tang、Guo-Bo Deng、Zhi-Qiang Wang、Ye-Xiang Xie、Yuan-Zhi Xia、Jin-Heng Li

  DOI：10.1021/jo300037n

  日期：2012.3.16

  A new, general method for the synthesis of spiro[4,5]trienores is described by the intramolecular ipso-halocyclization of 4-(p-unsubstituted-aryl)-1-alkynes. In the presence of halide electrophiles, a variety of 4-(p-unsubstituted-aryl)-1-alkynes underwent the intramolecular ipso-halocyclization with water smoothly, affording the corresponding halo-substituted spiro[4,5]trienones in moderate to good yields. The obtained spiro[4,5]trienones can be applied in constructing the azaquaternary tricyclic skeleton via Pd-catalyzed Heck reaction. Notably, the prepared spiro[4,5]trienones and azaquaternary tricycles are of importance in the areas of pharmaceuticals and agrochemicals. The mechanism of the intramolecular ipso-halocyclization reaction is also discussed according to the O-18-labeling experiments and DFT calculations.