3-[(2-Methoxyphenyl)amino]-1-phenyl-2-propen-1-one | 23688-12-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: 3-[(2-Methoxyphenyl)amino]-1-phenyl-2-propen-1-one
• 英文别名: 3-(2-methoxyanilino)-1-phenylprop-2-en-1-one
• CAS: 23688-12-2
• 化学式: C₁₆H₁₅NO₂
• 分子量: 253.301
• InChiKey: CSIKGNOPKQCSGF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  19
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.06
• 拓扑面积：
  38.3
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  3-[(2-Methoxyphenyl)amino]-1-phenyl-2-propen-1-one 在 对甲苯磺酰叠氮 、 sodium t-butanolate 作用下， 以 乙腈 为溶剂， 反应 2.0h， 以66 mg的产率得到1-(2-methoxyphenyl)-4-benzoyl-1H-1,2,3-triazole
  参考文献：
  名称：

  Base-Promoted Synthesis of N-Substituted 1,2,3-Triazoles via Enaminone–Azide Cycloaddition Involving Regitz Diazo Transfer

  摘要：

  The domino reactions between NH-based secondary enaminones and tosyl azide have been developed for the synthesis of various N-substituted 1,2,3-triazoles by employing t-BuONa as the base promoter. Through a key Regitz diazo-transfer process with tosyl azide, the reactions proceed efficiently at room temperature with good substrate tolerance.

  DOI：

  10.1021/acs.orglett.6b02975
• 作为产物：
  描述：

  1-phenyl-3-dimethylaminoprop-2-enone 、 邻甲氧基苯胺 在 iron(III) chloride 作用下， 以 乙腈 为溶剂， 反应 2.0h， 生成 3-[(2-Methoxyphenyl)amino]-1-phenyl-2-propen-1-one
  参考文献：
  名称：

  Base-Promoted Synthesis of N-Substituted 1,2,3-Triazoles via Enaminone–Azide Cycloaddition Involving Regitz Diazo Transfer

  摘要：

  The domino reactions between NH-based secondary enaminones and tosyl azide have been developed for the synthesis of various N-substituted 1,2,3-triazoles by employing t-BuONa as the base promoter. Through a key Regitz diazo-transfer process with tosyl azide, the reactions proceed efficiently at room temperature with good substrate tolerance.

  DOI：

  10.1021/acs.orglett.6b02975

文献信息

• Organocatalytic activation of isocyanides: N-heterocyclic carbene-catalyzed enaminone synthesis from ketones
  作者：Jungwon Kim、Soon Hyeok Hong

  DOI：10.1039/c6sc05266e

  日期：——

  suggested a novel role for the carbene in the activation of isocyanides, and a proton transfer process was found to be crucial for the generation of two activated species in the catalytic cycle. Various enaminones, some of which are not easily accessible by other methods, were synthesized in excellent yields. This study clearly demonstrates the potential of the nucleophilic activation of isocyanides in

  展示了使用 N-杂环卡宾 (NHC) 作为有机催化剂来活化异氰化物的第一个例子。根据之前关于 NHC 和异氰化物之间相互作用的报道，我们开发了一种涉及瞬态亚氨基中间体的催化循环。酮与异氰化物的反应高效地生成相应的烯胺酮。对照实验表明卡宾在异氰化物的活化中具有新的作用，并且发现质子转移过程对于催化循环中两种活化物质的生成至关重要。各种烯胺酮（其中一些不易通过其他方法获得）以优异的产率合成。这项研究清楚地证明了异氰化物的亲核活化在扩大其反应范围方面的潜力。
• Base-Promoted Synthesis of <i>N</i>-Substituted 1,2,3-Triazoles via Enaminone–Azide Cycloaddition Involving Regitz Diazo Transfer
  作者：Jie-Ping Wan、Shuo Cao、Yunyun Liu

  DOI：10.1021/acs.orglett.6b02975

  日期：2016.12.2

  The domino reactions between NH-based secondary enaminones and tosyl azide have been developed for the synthesis of various N-substituted 1,2,3-triazoles by employing t-BuONa as the base promoter. Through a key Regitz diazo-transfer process with tosyl azide, the reactions proceed efficiently at room temperature with good substrate tolerance.