2-ethyl-2,3-dihydro-1H-perimidine | 108903-03-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 2-ethyl-2,3-dihydro-1H-perimidine
• CAS: 108903-03-3
• 化学式: C₁₃H₁₄N₂
• 分子量: 198.268
• InChiKey: FPUPKCWCXYHRJG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4
• 重原子数：
  15
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.23
• 拓扑面积：
  24.1
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  3,5-二甲基吡唑-1-甲醇 、 2-ethyl-2,3-dihydro-1H-perimidine 以 乙腈 为溶剂， 反应 20.0h， 生成 2-ethyl-2,3-dihydro-1H-perimidine
  参考文献：
  名称：

  Monomeric Pd(II) complexes with trans-chelated pyrazole ligands as effective pre-catalysts for Heck cross-coupling reaction under mild aerobic conditions

  摘要：

  A new family of mononuclear palladium(II) complexes with bidentate trans-chelating pyrazole ligands [PdCl2(L-R)] (R = H, 1; Et, 2; Ph, 3; CHPh2, 4), where new ligand L-Et = 2-ethyl-1,3-bis-(3,5-dimethyl-pyrazol-1-ylmethyl)-2,3-dihydro-1H-perimidine, and a new mononuclear palladium(II) complex with monodentate trans-chelated pyrazole ligand [PdCl2(Ph-pz')(2)] (5), where Ph-pz' = 3,5-dimethyl-1-phenyl-1H-pyrazole, have been synthesized and characterized. Complexes 2-5 were also structurally confirmed by single crystal X-ray diffraction analysis. Remarkably, under very mild conditions (65-70 degrees C), complex 4 appeared to be an active pre-catalyst for the Heck coupling reactions of iodobenzene and t-butyl acrylate in MeOH. In the presence of co-catalyst [nNBu(4)]Br, however, complex 5 displayed the highest catalytic activity for the Heck reactions of activated bromobenzene and t-butyl acrylate. (C) 2013 Elsevier B. V. All rights reserved.

  DOI：

  10.1016/j.jorganchem.2013.08.016
• 作为产物：
  描述：

  丙醛 、 1,8-二氨基萘 以 水 为溶剂， 反应 0.5h， 以90%的产率得到2-ethyl-2,3-dihydro-1H-perimidine
  参考文献：
  名称：

  一种新型的无催化剂，环境友好的水方案，可用于合成2,3-二氢-1 H-亚氨基吡啶

  摘要：

  描述了在水上合成2,3-二氢-1 H-亚氨基吡啶的第一种最绿色的方法。使1,8-二氨基萘与不同类型的醛在室温下反应，以在30分钟内以中等至极好的收率提供该产品。还进行了克级反应，以确保反应的可扩展性。

  DOI：

  10.1016/j.tetlet.2019.150946

文献信息

• A novel catalyst‐free mechanochemical protocol for the synthesis of 2,3‐dihydro‐1<i>H</i>‐perimidines
  作者：Nissy Ann Harry、Sankaran Radhika、Mohan Neetha、Gopinathan Anilkumar

  DOI：10.1002/jhet.3880

  日期：2020.4

  A rapid, efficient, and green grinding assisted method for the synthesis of 2,3‐dihydro‐1H‐perimidines has been developed. 1,8‐Diaminonaphthalene and aldehydes were ground using mortar and pestle for 5 minutes affording the product in moderate to excellent yields. The methodology minimises the use of conventional workup and column chromatographic techniques.

  已经开发了一种快速，高效且绿色的研磨辅助方法，用于合成2,3-二氢-1 H-亚氨基吡啶。用研钵和研杵将1,8-二氨基萘和醛研磨5分钟，使产品收率适中至优异。该方法最大限度地减少了传统的后处理和柱色谱技术的使用。