N-allyl-N-(4-(trifluoromethyl)benzyl)prop-2-en-1-amine | 1371939-82-0

• 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-allyl-N-(4-(trifluoromethyl)benzyl)prop-2-en-1-amine
• 英文别名: 4-trifluoromethyl-N,N-diallylbenzamide；N-prop-2-enyl-N-[[4-(trifluoromethyl)phenyl]methyl]prop-2-en-1-amine
• CAS: 1371939-82-0
• 化学式: C₁₄H₁₆F₃N
• 分子量: 255.283
• InChiKey: JWLRYNAJIUNBPG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.88
• 重原子数：
  18.0
• 可旋转键数：
  6.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  3.24
• 氢给体数：
  0.0
• 氢受体数：
  1.0

反应信息

• 作为反应物：
  描述：

  萘 、 N-allyl-N-(4-(trifluoromethyl)benzyl)prop-2-en-1-amine 、 iron pentacarbonyl 在 sodium 作用下， 以 四氢呋喃 为溶剂， 以32%的产率得到tricarbonyl[(η2-N-allyl-N-allylamino)(4-(trifluoromethyl)phenyl)methylene]iron(0)
  参考文献：
  名称：

  Fischer aminocarbene complexes of chromium and iron: Anomalous electrochemical reduction of p-carbonyl substituted derivatives

  摘要：

  This contribution shows how a small change of a remote substituent (COOCH(3) for e.g. OCH(3)) on Fischer aminocarbene complexes can change totally the LUMO location, and thus electron distribution, extent of pi-electron delocalization and, consequently, redox properties of these potential catalysts. During investigation of redox properties of extended series of title compounds, an exceptionally positive reduction potential was observed (non fitting the LFER plot) for p-COOR substituents. This effect is caused by a strong intramolecular electronic interaction, which is specific for p-phenylene dicarbonyl compounds. In this context, the CN bond in aminocarbene moiety has a double bond character and resembles carbonyl function. The interpretation was proved by DFT calculations. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.electacta.2011.05.096
• 作为产物：
  描述：

  4-三氟甲基苯甲酸 、 二烯丙基胺 在 potassium phosphate 、 18-冠醚-6 、 苯硅烷 作用下， 以 四氢呋喃 为溶剂， 反应 12.0h， 以73%的产率得到N-allyl-N-(4-(trifluoromethyl)benzyl)prop-2-en-1-amine
  参考文献：
  名称：

  通过无过渡金属催化的羧酸直接将胺进行N-烷基/氟烷基化反应

  摘要：

  在简单的耐空气无机盐K 3 PO 4的催化下，已使用各种羧酸作为偶联剂构建了伯/仲胺直接N-单/二烷基/氟烷基化的可扩展方案。有利的特征包括100种实例，10种药物和类药物胺，氟化复杂的叔胺，克级合成和同位素标记胺，因此证明了该方法在工业上的潜在适用性。与减少酰胺中间体所需的传统反应性金属氢化物或硼氢化物相比，反应性较小的氢化硅的参与可能有助于显着的官能团相容性。

  DOI：

  10.1002/adsc.202000679

文献信息

• Direct <i>N‐</i> Alkylation/Fluoroalkylation of Amines Using Carboxylic Acids via Transition‐Metal‐Free Catalysis
  作者：Chunlei Lu、Zetian Qiu、Maojie Xuan、Yan Huang、Yongjia Lou、Yiling Zhu、Hao Shen、Bo‐Lin Lin

  DOI：10.1002/adsc.202000679

  日期：2020.10.6

  scalable protocol of direct N‐mono/di‐alkyl/fluoroalkylation of primary/secondary amines has been constructed with various carboxylic acids as coupling agents under the catalysis of a simple air‐tolerant inorganic salt, K3PO4. Advantageous features include 100 examples, 10 drugs and drug‐like amines, fluorinated complex tertiary amines, gram‐scale synthesis and isotope‐labelling amine, thus demonstrating

  在简单的耐空气无机盐K 3 PO 4的催化下，已使用各种羧酸作为偶联剂构建了伯/仲胺直接N-单/二烷基/氟烷基化的可扩展方案。有利的特征包括100种实例，10种药物和类药物胺，氟化复杂的叔胺，克级合成和同位素标记胺，因此证明了该方法在工业上的潜在适用性。与减少酰胺中间体所需的传统反应性金属氢化物或硼氢化物相比，反应性较小的氢化硅的参与可能有助于显着的官能团相容性。
• Fischer aminocarbene complexes of chromium and iron: Anomalous electrochemical reduction of p-carbonyl substituted derivatives
  作者：Irena Hoskovcová、Radka Zvěřinová、Jana Roháčová、Dalimil Dvořák、Tomáš Tobrman、Stanislav Záliš、Jiří Ludvík

  DOI：10.1016/j.electacta.2011.05.096

  日期：2011.7

  This contribution shows how a small change of a remote substituent (COOCH(3) for e.g. OCH(3)) on Fischer aminocarbene complexes can change totally the LUMO location, and thus electron distribution, extent of pi-electron delocalization and, consequently, redox properties of these potential catalysts. During investigation of redox properties of extended series of title compounds, an exceptionally positive reduction potential was observed (non fitting the LFER plot) for p-COOR substituents. This effect is caused by a strong intramolecular electronic interaction, which is specific for p-phenylene dicarbonyl compounds. In this context, the CN bond in aminocarbene moiety has a double bond character and resembles carbonyl function. The interpretation was proved by DFT calculations. (C) 2011 Elsevier Ltd. All rights reserved.