N-propargyl-piperonylamine | 779984-58-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并间二氧杂环戊烯类
• 英文名称: N-propargyl-piperonylamine
• 英文别名: N-(1,3-benzodioxol-5-ylmethyl)prop-2-yn-1-amine
• CAS: 779984-58-6
• 化学式: C₁₁H₁₁NO₂
• mdl: MFCD07411971
• 分子量: 189.214
• InChiKey: OAZAZZIZIXLSRN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  14
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.272
• 拓扑面积：
  30.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  N-propargyl-piperonylamine 在 二异丙胺 、 copper(I) bromide 作用下， 以 水 、 甲苯 为溶剂， 反应 24.0h， 生成
  参考文献：
  名称：

  Highly Selective Carboxylative Cyclization of Allenylmethylamines with Carbon Dioxide Using N-Heterocyclic Carbene-Silver(I) Catalysts

  摘要：

  Silver(I) carboxylate complexes promote the carboxylative cyclization of allenylmethylamines to afford 5-alkenyl-1,3-oxazolidin-2-ones in 2-propanol. The use of an N-heterocyclic carbene ligand (IPr) under pressurized CO2 is effective in suppressing the intramolecular hydroamination that leads to 2,5-dihydropyrroles. The mechanism involving a nucleophilic attack of the carbamate of the allene moiety and a subsequent protonation was realized on the basis of experimental and theoretical results involving a model intermediate, the alkenylgold(I) complex, which was synthesized from Au(OH)(IPr) and 1-methylamino-2,3-butadiene.

  DOI：

  10.1021/acs.orglett.5b00809
• 作为产物：
  描述：

  胡椒醛 、 炔丙胺 在 甲醇 、 溶剂黄146 、 sodium tetrahydroborate 作用下， 以80%的产率得到N-propargyl-piperonylamine
  参考文献：
  名称：

  可见光促进简单芳烃的分子内对环加成

  摘要：

  我们通过空间和电子无偏芳基片段的脱芳构化展示了桥接自行车的首次合成。可见光促进方法发生在室温下，具有足够的官能团耐受性。芳基伴侣双官能化的关键是使用萘作为添加剂，通过其扩展的 π 云稳定瞬态（双）自由基。这种效应可能导致它在激进序列中的广泛使用。

  DOI：

  10.1002/anie.202216817

文献信息

• Direct Conversion of CO 2  in Lime Kiln Waste Gas Catalyzed by a Copper‐Based N ‐heterocyclic Carbene Porous Polymer
  作者：Zhi-Xiu Rao、Pei-Bo Chen、Jin Xu、Qing Wang、Hai-Tao Tang、Ying Liang、Ying-Ming Pan

  DOI：10.1002/cssc.202300170

  日期：——

  copper-based N-heterocyclic carbene porous polymer (Cu@NHC-1) with triple synergistic catalytic effect on the conversion of CO2 via carboxylative cyclization was successfully fabricated to convert CO2 in lime kiln waste gas into value-added oxazolidinones, providing a prospect for the direct utilization of low concentration CO2 in industrial waste gas.

  发烟值：成功制备了具有三重协同催化作用的铜基N-杂环卡宾多孔聚合物（Cu@NHC-1）通过羧化环化转化CO 2 ，​​将石灰窑废气中的CO 2转化为附加值恶唑烷酮类化合物，为工业废气中低浓度CO 2的直接利用提供了前景。
• US4128656A
  申请人：——

  公开号：US4128656A

  公开（公告）日：1978-12-05
• Highly Selective Carboxylative Cyclization of Allenylmethylamines with Carbon Dioxide Using N-Heterocyclic Carbene-Silver(I) Catalysts
  作者：Kyohei Yamashita、Shun Hase、Yoshihito Kayaki、Takao Ikariya

  DOI：10.1021/acs.orglett.5b00809

  日期：2015.5.15

  Silver(I) carboxylate complexes promote the carboxylative cyclization of allenylmethylamines to afford 5-alkenyl-1,3-oxazolidin-2-ones in 2-propanol. The use of an N-heterocyclic carbene ligand (IPr) under pressurized CO2 is effective in suppressing the intramolecular hydroamination that leads to 2,5-dihydropyrroles. The mechanism involving a nucleophilic attack of the carbamate of the allene moiety and a subsequent protonation was realized on the basis of experimental and theoretical results involving a model intermediate, the alkenylgold(I) complex, which was synthesized from Au(OH)(IPr) and 1-methylamino-2,3-butadiene.
• Visible‐Light Promoted Intramolecular <i>para</i> ‐Cycloadditions on Simple Aromatics
  作者：Maurizio Chiminelli、Andrea Serafino、Davide Ruggeri、Luciano Marchiò、Franca Bigi、Raimondo Maggi、Max Malacria、Giovanni Maestri

  DOI：10.1002/anie.202216817

  日期：2023.3.13

  We present the first synthesis of bridged bicycles through the dearomatization of sterically and electronically unbiased aryl fragments. The visible-light promoted method occurs at room temperature and has ample functional-group tolerance. The key to the difunctionalization of the aryl partner is the use of naphthalene as an additive, which stabilizes transient (bi)radicals through its extended π cloud

  我们通过空间和电子无偏芳基片段的脱芳构化展示了桥接自行车的首次合成。可见光促进方法发生在室温下，具有足够的官能团耐受性。芳基伴侣双官能化的关键是使用萘作为添加剂，通过其扩展的 π 云稳定瞬态（双）自由基。这种效应可能导致它在激进序列中的广泛使用。