3-iodo-1-methyl-4-(4-acetylphenyl)-1-azaspiro[4.5]deca-3,6,9-triene-2,8-dione | 1078120-34-9

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 3-iodo-1-methyl-4-(4-acetylphenyl)-1-azaspiro[4.5]deca-3,6,9-triene-2,8-dione
• 英文别名: N-methyl-3-iodo-4-(p-acetylphenyl)-1-azaspiro[4,5]deca-3,6,9-triene-2,8-dione；4-(4-acetylphenyl)-3-iodo-1-methyl-1-azaspiro[4.5]deca-3,6,9-triene-2,8-dione
• CAS: 1078120-34-9
• 化学式: C₁₈H₁₄INO₃
• 分子量: 419.219
• InChiKey: CPINIMACFCYQIM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  23
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  54.4
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  N-(4-methoxyphenyl)-N-methylpropiolamide 在 bis-triphenylphosphine-palladium(II) chloride 、 copper(l) iodide 、 氧气 、 sodium acetate 、 三乙胺 、 [双(三氟乙酰氧基)碘]苯 作用下， 以 四氢呋喃 、 乙腈 为溶剂， 反应 18.0h， 生成 3-iodo-1-methyl-4-(4-acetylphenyl)-1-azaspiro[4.5]deca-3,6,9-triene-2,8-dione
  参考文献：
  名称：

  用PhI（OCOCF3）2和KBr / KCl光导合成N-芳基炔酰胺的卤代螺[4,5]三烯酮。

  摘要：

  已经开发出新颖且方便的N-（对甲氧基芳基）丙酰胺的光介导的卤代螺环化。苯碘双（三氟乙酸盐）（PIFA）作为碘化试剂的光解在氙灯的照射下导致碘化ipso环化，而溴化的ipso环化或氯化的ipso环化则通过照射PIFA和KBr / KCl在蓝色LED下。本协议只是利用光作为安全，清洁的能源，不需要任何外部光催化剂即可提供各种3-卤代螺[4,5]三烯酮，产率高至优异（高达93％）。

  DOI：

  10.1039/d0ob00057d

文献信息

• 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.
• 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.