N-methyl-3-iodo-4-phenyl-1-azaspiro[4,5]-deca-3,6,8-triene-2,10-dione | 1013906-18-7

• 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: N-methyl-3-iodo-4-phenyl-1-azaspiro[4,5]-deca-3,6,8-triene-2,10-dione
• 英文别名: 3-Iodo-1-methyl-4-phenyl-1-azaspiro[4.5]deca-3,7,9-triene-2,6-dione
• CAS: 1013906-18-7
• 化学式: C₁₆H₁₂INO₂
• 分子量: 377.181
• InChiKey: IWDCGBXVGHIDCZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  20
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.12
• 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-(2-methoxyphenyl)-N-methyl-3-phenylpropiolamide 在 N-碘代丁二酰亚胺 、 溶剂黄146 作用下， 反应 3.0h， 以53%的产率得到N-methyl-3-iodo-4-phenyl-1-azaspiro[4,5]-deca-3,6,8-triene-2,10-dione
  参考文献：
  名称：

  Selective Synthesis of Spiro[4,5]trienyl Acetates via an Intramolecular Electrophilic ipso-Iodocyclization Process

  摘要：

  A general and efficient intramolecular electrophilic ipso-iodocyclization of para-unactivated arylalkynes has been developed for the synthesis of spiro[4,5]trienyl acetates. In the presence of NIS (N-iodosuccimide) and HOAc, para-unactivated arylalkynes, including N-arylpropiolamides and phenyl 3-phenylpropiolate, underwent the intramolecular electrophilic ipso-iodocyclization smoothly in moderate to good yields.

  DOI：

  10.1021/ol703050z

文献信息

• ipso-Iodocyclization of Ethoxyethyl Ethers to Alkynes at the ortho-Position: An Efficient Synthesis of Functionalized Spiro Compounds
  作者：Akimori Wada、Takashi Okitsu、Daisuke Nakazawa、Akihiro Kobayashi、Masahiro Mizohata、Yasuko In、Toshimasa Ishida

  DOI：10.1055/s-0029-1218569

  日期：2010.1

  An efficient approach to the synthesis of azaspiro compounds having dissymmetric dienone cores was achieved by ipso-iodocyclization of ethoxyethyl ether to alkynes. When the linker was an ether or an ester, domino iodocyclizaion/Diels-Alder reaction proceeded to afford the dimer, which can be transformed into the bridgehead-spiro connection ring system by a domino retro-­Diels-Alder/Diels-Alder process.

  通过乙氧基乙基醚与炔烃的异碘环化反应，实现了合成具有不对称二烯酮核心的氮杂环化合物的有效方法。当连接物为醚或酯时，多米诺碘环化/Diels-Alder 反应产生二聚物，二聚物可通过多米诺逆 Diels-Alder/Diels-Alder 过程转化为桥头螺连接环系统。