3-bromo-1-methyl-4-(o-tolyl)-1-azaspiro[4.5]deca-3,6,9-triene-2,8-dione | 1078120-38-3

• 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: 3-bromo-1-methyl-4-(o-tolyl)-1-azaspiro[4.5]deca-3,6,9-triene-2,8-dione
• 英文别名: 3-Bromo-1-methyl-4-(2-methylphenyl)-1-azaspiro[4.5]deca-3,6,9-triene-2,8-dione
• CAS: 1078120-38-3
• 化学式: C₁₇H₁₄BrNO₂
• 分子量: 344.208
• InChiKey: VBAIENQFEQNVTH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 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-methyl-N-phenyl-3-(o-tolyl)propiolamide 在 Oxone 、 水 、 zinc dibromide 作用下， 以 乙腈 为溶剂， 以80%的产率得到3-bromo-1-methyl-4-(o-tolyl)-1-azaspiro[4.5]deca-3,6,9-triene-2,8-dione
  参考文献：
  名称：

  ZnBr 2介导的丙酰胺酰胺的氧化螺-溴环化反应，用于合成3-溴-1-azaspiro [4.5] deca-3,6,9-三烯-2,8-二酮†

  摘要：

  本文已经描述了ZnBr 2介导的N-芳基丙酰胺酰胺的氧化螺-溴环化，用于高效合成3-溴-1-氮杂螺[4.5] deca-3,6,9-三烯-2,8-二酮。将一当量的水引入到最终产品中。该反应在室温下有效地进行，并且显示出优异的官能团耐受性。在标准条件下，3-溴-1-氧杂螺[4.5] deca-3,6,9-三烯-2,8-二酮和3-溴-1-氮杂螺[4.5] deca-3,6,9-trien-合成了8个。

  DOI：

  10.1039/c7ob00293a

文献信息

• Electrochemical Oxidative Halogenation of <i>N</i>-Aryl Alkynamides for the Synthesis of Spiro[4.5]trienones
  作者：Ke Yu、Xianqiang Kong、Jiajun Yang、Guodong Li、Bo Xu、Qianjin Chen

  DOI：10.1021/acs.joc.0c02429

  日期：2021.1.1

  We developed a green method for the synthesis of spiro[4.5]trienones through an electrochemical oxidative halocyclization with N-aryl alkynamides. This reaction was conducted under metal-catalyst- and exogenous-oxidant-free conditions at room temperature. Using readily available LiCl, LiBr, and LiI as the halogen source, a variety of dearomative halo-spirocyclization products were obtained in good

  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。
• 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。
• Electrophilic <i>ipso</i>-Cyclization of <i>N</i>-(<i>p</i>-Methoxyaryl)propiolamides Involving an Electrophile-Exchange Process
  作者：Bo-Xiao Tang、Qin Yin、Ri-Yuan Tang、Jin-Heng Li

  DOI：10.1021/jo8018297

  日期：2008.11.21

  A novel electrophilic ipso-cyclization involving an electrophile-exchange process has been developed. In the presence of CuX (X = I, Br, SCN) and electrophilic fluoride reagents, a variety of N-(p-methoxyaryl)propiolamides and 4-methoxyphenyl 3-phenylpropiolate were cyclized to selectively afford the corresponding spiro[4.5]decenones in moderate to good yields. It is noteworthy that two azaquaternary tricyclic products were synthesized through a two-step pathway involving an electrophilic ipso-cyclization and then an intramolecular Heck reaction.