N-(4-methoxyphenyl)-N-methylbut-2-ynamide | 1078120-23-6

• 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: N-(4-methoxyphenyl)-N-methylbut-2-ynamide
• CAS: 1078120-23-6
• 化学式: C₁₂H₁₃NO₂
• 分子量: 203.241
• InChiKey: ZPLTZLZNZBRBEB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.68
• 重原子数：
  15.0
• 可旋转键数：
  2.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  29.54
• 氢给体数：
  0.0
• 氢受体数：
  2.0

反应信息

• 作为反应物：
  描述：

  N-(4-methoxyphenyl)-N-methylbut-2-ynamide 在 copper(l) iodide 、 1-fluoro-2,4,6-trimethylpyridin-1-ium tetrafluoroborate 作用下， 以 乙腈 为溶剂， 反应 6.0h， 以41%的产率得到3-iodo-1,4-dimethyl-1-azaspiro[4.5]deca-3,6,9-triene-2,8-dione
  参考文献：
  名称：

  Electrophilic ipso-Cyclization of N-(p-Methoxyaryl)propiolamides Involving an Electrophile-Exchange Process

  摘要：

  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.

  DOI：

  10.1021/jo8018297

文献信息

• Visible-light-enabled spirocyclization of alkynes leading to 3-sulfonyl and 3-sulfenyl azaspiro[4,5]trienones
  作者：Wei Wei、Huanhuan Cui、Daoshan Yang、Huilan Yue、Chenglong He、Yulong Zhang、Hua Wang

  DOI：10.1039/c7gc02330h

  日期：——

  A visible-light-induced strategy has been established for the synthesis of 3-sulfonyl and 3-sulfenyl azaspiro[4,5]trienones at room temperature in air.

  已在室温下空气中合成3-磺酰基和3-磺基氮杂螺[4,5]三烯酮的可见光诱导策略。
• Visible-light promoted one-pot synthesis of sulfonated spiro[4,5]trienones from propiolamides, anilines and sulfur dioxide under transition metal-free conditions
  作者：Yu Liu、Qiao-Lin Wang、Zan Chen、Quan Zhou、Bi-Quan Xiong、Pan-Liang Zhang、Ke-Wen Tang

  DOI：10.1039/c9cc05949k

  日期：——

  A novel visible-light promoted sulfonylation/ipso-cyclization of N-arylpropiolamides with aromatic amines and DABCO·(SO₂)₂ to synthesize various sulfonated spiro[4,5]trienones is reported.

  报道了一种新颖的可见光促进的N-芳基丙炔酰胺与芳香胺和DABCO·(SO2)2进行磺化/ipso-环化反应，合成各种磺化的螺[4,5]三烯酮。
• Electrochemical Synthesis of Spiro[4.5]trienones through Radical‐Initiated Dearomative Spirocyclization
  作者：Jiawei Hua、Zheng Fang、Mixue Bian、Tao Ma、Man Yang、Jia Xu、ChengKou Liu、Wei He、Ning Zhu、Zhao Yang、Kai Guo

  DOI：10.1002/cssc.202000098

  日期：2020.4.21

  A novel and green route has been developed for the electrochemical synthesis of spiro[4.5]trienones through radical-initiated dearomative spirocyclization of alkynes with diselenides. This metal-free and oxidant-free electrosynthesis reaction was performed in an undivided cell under mild conditions. A variety of selenation spiro[4.5]trienones products were prepared in moderate-to-good yields, showing

  已经开发了一种新颖的绿色路线，用于通过自由基引发的炔烃与二硒化物的螺合成[4.5]三烯酮的电化学合成。这种无金属和无氧化剂的电合成反应是在温和条件下在未分裂的电池中进行的。以中等到良好的产率制备了多种硒化螺[4.5]三烯酮产品，显示出广泛的范围和对官能团的耐受性。而且，与电合成相结合的已开发的连续流系统具有实现放大反应的潜力，克服了常规电化学放大反应的低效率。
• Expeditious Access to Spiro-Fused 2,5-Cyclohexadienones <i>via</i> Thio(seleno)cyanative <i>ipso</i>-Cyclization
  作者：Chada Raji Reddy、Uprety Ajaykumar、Dattahari H. Kolgave

  DOI：10.1021/acs.joc.0c02270

  日期：2020.12.4

  A facile oxidative dearomatization of N-(p-methoxyaryl)propiolamides has been established for the synthesis of spiro-fused 2,5-cyclohexadienone frameworks via thio(seleno)cyanative ipso-cyclization in the presence of ceric ammonium nitrate (CAN) as the oxidant. The present method, involving the formation of C–S and C–C bonds, was also extended to (p-methoxyaryl)propiolates for thiocyanative ipso-cyclization

  的一种简便的氧化脱芳构化ñ - （p -methoxyaryl）propiolamides已建立螺稠合的2,5-环己二烯酮框架的合成通过硫代（硒）cyanative本位-cyclization在硝酸铈铵（CAN）作为存在氧化剂。本发明的方法，涉及C-S和C-C键的形成，也扩展到（p -methoxyaryl）的丙炔酸酯为thiocyanative本位-cyclization。此外，将获得的硫属元素基-螺环己二酮转化为独特官能化的螺环己二酮衍生物。
• An electrophilic thiocyanation/ipso-cyclization leading to spirocyclohexadienones
  作者：Zhihua Qiao、Chukai Shao、Yong Gao、Kun Liang、Hongquan Yin、Fu-Xue Chen

  DOI：10.1016/j.tetlet.2022.153875

  日期：2022.6

  A Lewis acid-catalyzed cyclization of N-(p-methoxyphenyl)-3-phenylpropionamide with N-thiocyanosuccinimide has been accomplished under mild conditions. Thus, a series of thiocyanato-containing spirocyclohexadienones was obtained in moderate to excellent yields with a good functional group tolerance and a wide range of substrates. It provides an alternative approach for the synthesis of functionalized

  路易斯酸催化的N- (对甲氧基苯基)-3-苯基丙酰胺与N-硫氰基琥珀酰亚胺的环化反应在温和条件下完成。因此，以中等至优异的产率获得了一系列含硫氰酸根的螺环己二烯酮，具有良好的官能团耐受性和广泛的底物。它提供了一种合成功能化螺环己二烯酮的替代方法。