[[4-(三氟甲基)苯基]氨基]-乙腈 | 672333-10-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 中文名称: [[4-(三氟甲基)苯基]氨基]-乙腈
• 英文名称: 2-((4-(trifluoromethyl) phenyl) amino) acetonitrile
• 英文别名: {[4-(Trifluoromethyl)phenyl]amino}acetonitrile；2-[4-(trifluoromethyl)anilino]acetonitrile
• CAS: 672333-10-7
• 化学式: C₉H₇F₃N₂
• 分子量: 200.163
• InChiKey: DGHUIZKWEQEOTN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  14
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  35.8
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  [[4-(三氟甲基)苯基]氨基]-乙腈 在 selenium 、 三乙胺 作用下， 以 二氯甲烷 为溶剂， 生成
  参考文献：
  名称：

  Design, synthesis and glutathione peroxidase-Like properties of ovothiol-Derived diselenides

  摘要：

  Eleven imidazole diselenides derived from the naturally occurring family of antioxidants, the ovothiols, were synthetised by cyclisation of selenoamides with trimethylsilyltrifluoromethanesulfonate or refluxing of cyanoamines in a selenium/sodium borohydride mixture. These compounds were assayed for their glutathione peroxidase-like (GSH Px-like) activity and their capacity to be reduced by glutathione. The most active molecules of the series were 4 times more potent in the GSH Px-like test than the widely known reference compound, ebselen. This catalytic activity was mediated by the formation of the antioxidant selenol intermediate upon partial but significant exchange reaction with glutathione. (C) 2003 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/s0968-0896(03)00504-2
• 作为产物：
  描述：

  C₁₂H₁₅F₃N₂Si 在 水 作用下， 以 四氢呋喃 、 甲苯 为溶剂， 以73 %的产率得到[[4-(三氟甲基)苯基]氨基]-乙腈
  参考文献：
  名称：

  甲醛与 TMSCN 的 Strecker 反应，由 TBAF 和甲酸催化：伯胺的 N-单氰基甲基化

  摘要：

  报告了甲醛、胺和 TMSCN 的 Strecker 反应的一组条件，该反应提供三组分偶联加合物作为主要产物。HCOOH 和 TBAF 用作助催化剂，TMSCN 用作氰化物源和胺的保护剂。结果，副反应得到有效抑制，范围广泛的芳香族和脂肪族胺以 52-99% 的产率被单氰甲基化。此外，该协议已成功应用于间二酰胺杀虫剂的合成。

  DOI：

  10.1002/adsc.202200767

文献信息

• Copper-Catalyzed Three- Five- or Seven-Component Coupling Reactions: The Selective Synthesis of Cyanomethylamines, N,N-Bis(Cyanomethyl)Amines and N,N'-Bis(Cyanomethyl)Methylenediamines Based on a Strecker-Type Synthesis
  作者：Norio Sakai、Nobuaki Takahashi、Daiki Inoda、Reiko Ikeda、Takeo Konakahara

  DOI：10.3390/molecules181012488

  日期：——

  We have demonstrated that a cooperative catalytic system comprised of CuCl and Cu(OTf)2 could be used to effectively catalyse the three-, five- and seven-component coupling reactions of aliphatic or aromatic amines, formaldehyde, and trimethylsilyl cyanide (TMSCN), and selectively produce in good yields the corresponding cyanomethylamines, N,N-bis(cyanomethyl)amines and N,N'-bis(cyanomethyl)methylenediamines.

  我们已经证明，由CuCl和Cu(OTf)2组成的协同催化系统可以有效催化脂肪族或芳香族胺、甲醛和三甲基硅基氰化物（TMSCN）的三元、五元和七元偶联反应，并选择性地以良好的产率生成相应的氰甲基胺、N,N-双（氰甲基）胺和N,N'-双（氰甲基）亚甲基二胺。
• 一种胺的氰甲基化方法
  申请人：沈阳化工大学

  公开号：CN117342978A

  公开（公告）日：2024-01-05

  氰甲基胺的结构存在于许多生物活性分子和天然化合物中，是许多农药和医药合成的关键中间体。本发明提供了一种胺的氰甲基化方法。该方法使用胺与甲醛、三甲基氰硅烷进行Strecker反应生成相应的氰甲基化产物，得到的产物收率高、条件温和，适合工业化生产，具有良好的应用前景。
• Design, synthesis and glutathione peroxidase-Like properties of ovothiol-Derived diselenides
  作者：Fabrice Bailly、Nathalie Azaroual、Jean-Luc Bernier

  DOI：10.1016/s0968-0896(03)00504-2

  日期：2003.10

  Eleven imidazole diselenides derived from the naturally occurring family of antioxidants, the ovothiols, were synthetised by cyclisation of selenoamides with trimethylsilyltrifluoromethanesulfonate or refluxing of cyanoamines in a selenium/sodium borohydride mixture. These compounds were assayed for their glutathione peroxidase-like (GSH Px-like) activity and their capacity to be reduced by glutathione. The most active molecules of the series were 4 times more potent in the GSH Px-like test than the widely known reference compound, ebselen. This catalytic activity was mediated by the formation of the antioxidant selenol intermediate upon partial but significant exchange reaction with glutathione. (C) 2003 Elsevier Ltd. All rights reserved.
• Strecker Reactions of Formaldehyde with TMSCN, Catalyzed by TBAF and Formic Acid: <i>N</i> ‐Monocyanomethylation of Primary Amines
  作者：Yunting Liu、Jing Zhang、Jianyu Zhang、Hongyan Pei、Xuegui Liu、Hui Jin、Do Hyun Ryu、Lixin Zhang

  DOI：10.1002/adsc.202200767

  日期：2023.1.10

  Strecker reaction of formaldehyde, amines, and TMSCN that affords three-component coupling adducts as the major products is reported. HCOOH and TBAF are used as cocatalysts and the TMSCN functions as both cyanide source and protecting reagent for amines. As a result, the side reactions were suppressed efficiently and a broad range of aromatic and aliphatic amines were mono-cyanomethylated in 52–99%

  报告了甲醛、胺和 TMSCN 的 Strecker 反应的一组条件，该反应提供三组分偶联加合物作为主要产物。HCOOH 和 TBAF 用作助催化剂，TMSCN 用作氰化物源和胺的保护剂。结果，副反应得到有效抑制，范围广泛的芳香族和脂肪族胺以 52-99% 的产率被单氰甲基化。此外，该协议已成功应用于间二酰胺杀虫剂的合成。