2-deuterio-2-diazo-1,1,1-trifluoro-ethane

• 分子结构分类: 有机化合物 - 有机1,3-偶极化合物 - 炔丙基型1，3-偶极有机化合物
• 英文名称: 2-deuterio-2-diazo-1,1,1-trifluoro-ethane
• 化学式: C₂HF₃N₂
• 分子量: 111.031
• InChiKey: YWUIUNGMQOICND-MICDWDOJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.85
• 重原子数：
  7.0
• 可旋转键数：
  0.0
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  36.4
• 氢给体数：
  0.0
• 氢受体数：
  0.0

反应信息

• 作为反应物：
  描述：

  2-deuterio-2-diazo-1,1,1-trifluoro-ethane 、 (E)-methyl 2-((4-chlorobenzylidene)amino)acetate 在 silver(I) acetate 、 caesium carbonate 作用下， 以 四氢呋喃 为溶剂， 反应 24.0h， 以95%的产率得到C₁₂H₁₀⁽²⁾HClF₃N₃O₂
  参考文献：
  名称：

  Silver-Catalyzed [3 + 3] Dipolar Cycloaddition of Trifluorodiazoethane and Glycine Imines: Access to Highly Functionalized Trifluoromethyl-Substituted Triazines and Pyridines

  摘要：

  Herein we disclose a silver-catalyzed [3 + 3] 1,3-dipolar cycloaddition reaction of trifluorodiazoethane with glycine imines. This reaction exhibits manifold remarkable features, such as easily available substrates, high regio- and diastereoselectivities, mild reaction conditions, and good yields across a broad spectrum of substrates. Moreover, swift transformations of the obtained tetrahydrotriazines provide efficient access to a diverse set of highly functionalized trifluoromethyl-substituted triazines and pyridines. Particularly noteworthy is that such trifluoromethylated 1,2,4-triazines demonstrate competent reactivity toward trans-cyclooctene (TCO) derivatives with second-order rate constants (k(2)) up to 99.24 M-1 s(-1), which represents the highest value involving 1,2,4-triazines to date.

  DOI：

  10.1021/acscatal.9b00846
• 作为产物：
  描述：

  2,2,2-三氟乙胺盐酸盐 在 sodium nitrite 作用下， 以 水 、 重水 为溶剂， 反应 2.0h， 生成 2-deuterio-2-diazo-1,1,1-trifluoro-ethane
  参考文献：
  名称：

  CF3CHN2，腈和醛的铜引发的三组分反应：CF3取代的恶唑啉和邻氨基氨基醇的非对映选择性合成

  摘要：

  描述了一种新颖的三组分C‒C，C‒N和C‒O键形成反应。在20摩尔％CuO的存在下，CF3CHN2，腈和醛的缩合反应进行，得到...

  DOI：

  10.1039/c5cc02749g

文献信息

• Radical-initiated diazo-retaining nucleophilic addition reaction of trifluorodiazoethane and diazoacetate with 2H‑azirines
  作者：Yue-Ji Chen、Jie Zheng、Jun-An Ma、Fa-Guang Zhang

  DOI：10.1016/j.jfluchem.2023.110129

  日期：2023.5

  A diethylzinc-air system is established to enable an unconventional diazo-retaining nucleophilic addition reaction of trifluorodiazoethane and diazoacetate with 2H-azirines. This transformation converted a broad range of cyclic 2H-azirines to valuable acyclic α-diazo amines in good yields. Further synthetic transformations provide access to β-CF3 amines, β-CF3-enamines, and CF3-oxazolines. Preliminary

  建立了二乙基锌-空气体系，以实现三氟重氮乙烷和重氮乙酸酯与 2 H-氮杂环丙烷的非常规保留重氮基的亲核加成反应。这种转化以良好的产率将范围广泛的环状 2 H-氮杂环化合物转化为有价值的无环 α-重氮胺。进一步的合成转化提供了获得 β-CF 3胺、β-CF 3 -烯胺和 CF 3 -恶唑啉的途径。初步的机理研究表明，分子氧在实现这种自由基引发的反应中起着至关重要的作用，涉及原位生成的亚胺作为关键中间体。
• Silver-Catalyzed [3 + 3] Dipolar Cycloaddition of Trifluorodiazoethane and Glycine Imines: Access to Highly Functionalized Trifluoromethyl-Substituted Triazines and Pyridines
  作者：Zhen Chen、Nan Ren、Xiaoxiao Ma、Jing Nie、Fa-Guang Zhang、Jun-An Ma

  DOI：10.1021/acscatal.9b00846

  日期：2019.5.3

  Herein we disclose a silver-catalyzed [3 + 3] 1,3-dipolar cycloaddition reaction of trifluorodiazoethane with glycine imines. This reaction exhibits manifold remarkable features, such as easily available substrates, high regio- and diastereoselectivities, mild reaction conditions, and good yields across a broad spectrum of substrates. Moreover, swift transformations of the obtained tetrahydrotriazines provide efficient access to a diverse set of highly functionalized trifluoromethyl-substituted triazines and pyridines. Particularly noteworthy is that such trifluoromethylated 1,2,4-triazines demonstrate competent reactivity toward trans-cyclooctene (TCO) derivatives with second-order rate constants (k(2)) up to 99.24 M-1 s(-1), which represents the highest value involving 1,2,4-triazines to date.
• Copper-triggered three-component reaction of CF₃CHN₂, nitriles, and aldehydes: highly diastereoselective synthesis of CF₃-substituted oxazolines and vicinal amino alcohols
  作者：Ai-Jie Cai、Yan Zheng、Jun-An Ma

  DOI：10.1039/c5cc02749g

  日期：——

  A novel, three-component C‒C, C‒N and C‒O bonds forming reaction is described. In the presence of 20 mol% CuO, this condensation reaction of CF3CHN2, nitriles, and aldehydes proceeds to afford...

  描述了一种新颖的三组分C‒C，C‒N和C‒O键形成反应。在20摩尔％CuO的存在下，CF3CHN2，腈和醛的缩合反应进行，得到...