3-amino-1-phenyl-3-p-tolylprop-2-en-1-one | 52939-90-9

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 直链 1,3-二芳基丙烷
• 英文名称: 3-amino-1-phenyl-3-p-tolylprop-2-en-1-one
• 英文别名: 1-phenyl-3-(p-tolylamino)prop-2-en-1-one；Agn-PC-036ewq；3-amino-3-(4-methylphenyl)-1-phenylprop-2-en-1-one
• CAS: 52939-90-9
• 化学式: C₁₆H₁₅NO
• 分子量: 237.301
• InChiKey: PIIXWKIYIRGSFA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  18
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.06
• 拓扑面积：
  43.1
• 氢给体数：
  1
• 氢受体数：
  2

安全信息

• 海关编码：
  2922399090

反应信息

• 作为反应物：
  描述：

  3-amino-1-phenyl-3-p-tolylprop-2-en-1-one 在 盐酸羟胺 作用下， 以 乙腈 为溶剂， 反应 6.0h， 以91%的产率得到3-(4-甲基苯基)-5-苯基-1,2-恶唑
  参考文献：
  名称：

  Radical Enamination of Vinyl Azides: Direct Synthesis of N-Unprotected Enamines

  摘要：

  An electron-withdrawing-group-generable radical-induced enamination of vinyl azides is reported, which results in a variety of beta-functionalized N-unprotected enamines in a stereoselective manner. A plausible mechanism involving an unusual 1,3-H transfer of in situ generated iminyl radical intermediate was proposed on the basis of experimental results and DFT calculations.

  DOI：

  10.1021/acs.orglett.7b03204
• 作为产物：
  描述：

  4-甲苯基乙炔 在 copper(l) iodide 、 叠氮基三甲基硅烷 、 水 、 silver carbonate 作用下， 以 二甲基亚砜 、 乙腈 为溶剂， 反应 6.0h， 生成 3-amino-1-phenyl-3-p-tolylprop-2-en-1-one
  参考文献：
  名称：

  Radical Enamination of Vinyl Azides: Direct Synthesis of N-Unprotected Enamines

  摘要：

  An electron-withdrawing-group-generable radical-induced enamination of vinyl azides is reported, which results in a variety of beta-functionalized N-unprotected enamines in a stereoselective manner. A plausible mechanism involving an unusual 1,3-H transfer of in situ generated iminyl radical intermediate was proposed on the basis of experimental results and DFT calculations.

  DOI：

  10.1021/acs.orglett.7b03204

文献信息

• Amine-catalyzed synthesis of N2-sulfonyl 1,2,3-triazole in water and the tunable N2-H 1,2,3-triazole synthesis in DMSO via metal-free enamine annulation
  作者：Yanhui Guo、Yunyun Liu、Jie-Ping Wan

  DOI：10.1016/j.cclet.2021.08.003

  日期：2022.2

  N2-H 1,2,3-triazoles via organocatalytic annulation of enaminone/enaminoester with sulfonyl azide has been realized. The unconventional selectivity providing N2-sulfoyl 1,2,3-triazoles takes place in pure water, wherein the hydrogen bond effect between water and the intermediate resulting from enamine-azide corporation accounts for the novel reaction selectivity. On the other hand, the reactions conducted

  实现了烯胺酮/烯胺酯与磺酰叠氮的有机催化环化选择性合成N 2 -磺酰基和N 2 -H 1,2,3-三唑。提供N 2 -磺酰基1,2,3-三唑的非常规选择性发生在纯水中，其中水和烯胺-叠氮化物产生的中间体之间的氢键作用解释了新的反应选择性。另一方面，在没有这种氢键效应的情况下，在 DMSO 中进行的反应特异性地提供了N 2 -H 1,2,3-三唑。
• 2,3‐Dichloro‐5,6‐Dicyano‐1,4‐Benzoquinone (DDQ)‐Mediated Tandem Oxidative Coupling/Intramolecular Annulation/Dehydro‐Aromatization for the Synthesis of Polysubstituted and Fused Pyridines
  作者：Dongping Cheng、Zhiteng Deng、Xianhang Yan、Mingliang Wang、Xiaoliang Xu、Jizhong Yan

  DOI：10.1002/adsc.201900956

  日期：2019.11.5

  A DDQ‐mediated tandem reaction of 1,3‐diarylpropenes and β‐enaminoesters/4‐aminocoumarins is disclosed. It involves oxidative coupling, intramolecular annulation and dehydro‐aromatization reaction, which provides an efficient and mild method for the synthesis of polysubstituted and fused pyridines under metal‐free conditions.

  披露了一种由DDQ介导的1,3-二芳基丙烯和β-氨基酯/ 4-氨基香豆素的串联反应。它涉及氧化偶联，分子内环化和脱氢芳香化反应，这为在无金属条件下合成多取代和稠合吡啶提供了一种有效而温和的方法。
• Asymmetric Aza-Diels–Alder Reactions of in Situ Generated β,β-Disubstituted α,β-Unsaturated N–H Ketimines Catalyzed by Chiral Phosphoric Acids
  作者：Shunlong He、Huanchao Gu、Yu-Peng He、Xiaoyu Yang

  DOI：10.1021/acs.orglett.0c01994

  日期：2020.7.17

  A novel asymmetric synthesis of dihydropyridinones with vicinal quaternary stereocenters has been realized by asymmetric aza-Diels–Alder reactions of 3-amido allylic alcohols with oxazolones enabled by chiral phosphoric acid catalysis. A series of aryl/alkyl- and alkyl/alkyl-disubstituted 3-amido allylic tertiary alcohols and 4-substituted oxazolones could be well tolerated in these reactions, producing

  通过手性磷酸催化的3-酰胺基烯丙基醇与恶唑酮的不对称aza-Diels-Alder反应，已经实现了具有邻位四级立体中心的二氢吡啶酮的新型不对称合成。在这些反应中可以很好地耐受一系列芳基/烷基-和烷基/烷基-二取代的3-酰胺基烯丙基叔醇和4-取代的恶唑酮，从而产生具有优异的非对映选择性和高对映选择性的二氢吡啶并酮。进行了机理研究和对照实验以阐明反应机理，其中提出了构型定义的β，β-二取代α，β-不饱和NH酮亚胺作为关键中间体。
• Solid-State Synthesis of β-Enamino Ketones from Solid 1,3-Dicarbonyl Compounds and Ammonium Salts or Amines
  作者：Jing-Hua Li、Shi-Liang Xu、Cheng-Ping Li

  DOI：10.1055/s-0028-1087914

  日期：——

  A facile amination of solid 1,3-dicarbonyl compounds with ammonium salts or amines in solid state has been achieved by mechanochemical grinding in the presence of KHSO4 and SiO2. Most of the reactions proceed smoothly at room temperature under solid-state conditions and give their corresponding β-imino derivatives in high yields. The method has the advantage of simple manipulation and mild conditions.

  通过机械化学研磨法，在KHSO4和SiO2的存在下，实现了固态下1,3-二羰基化合物与铵盐或胺的便捷胺化反应。大多数反应在室温下的固态条件下顺利进行，并高产率地得到相应的β-亚氨基衍生物。该方法具有操作简单和条件温和的优势。
• Copper-catalyzed aldol-type addition of ketones to aromatic nitriles: a simple approach to enaminone synthesis
  作者：Xiaoqiang Yu、Longxiang Wang、Xiujuan Feng、Ming Bao、Yoshinori Yamamoto

  DOI：10.1039/c3cc40466h

  日期：——

  An efficient method for the synthesis of enaminones is described. The aldol-type addition of ketones to aromatic nitriles proceeded smoothly in the presence of a simple copper catalyst system (CuI–2,2′-bipyridine–NaOtBu) in N,N-dimethylformamide. Enaminones in satisfactory to excellent yields were produced using this technique.

  描述了一种高效的酮亚胺合成方法。在N,N-二甲基甲酰胺中，酮与芳香腈的醇醛型加成在简单的铜催化剂体系（CuI–2,2′-联吡啶–NaOtBu）的存在下顺利进行。采用该技术合成的酮亚胺产率令人满意至优异。