2-Imino-6-nitrochromene-3-carbonitrile | 890879-65-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并吡喃
• 英文名称: 2-Imino-6-nitrochromene-3-carbonitrile
• CAS: 890879-65-9
• 化学式: C₁₀H₅N₃O₃
• 分子量: 215.168
• InChiKey: FJLZPTYGQSJCKA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  16
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  103
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  3,5-二甲基-4-硝基异噁唑 、 2-Imino-6-nitrochromene-3-carbonitrile 以 水 为溶剂， 反应 2.0h， 生成 2-amino-4-((3-methyl-4-nitroisoxazol-5-yl)methyl)-6-nitro-4H-chromene-3-carbonitrile
  参考文献：
  名称：

  Synthesis of 4 H ‐chromene‐isoxazole hybrids via ortho ‐hydroxy directing cyclization of isoxazole‐styrenes and Michael addition of imino‐chromenes in aqueous medium

  摘要：

  AbstractA green, efficient, and one‐pot method synthesis of functionalized 4H‐chromene‐isoxazole hybrids is reported via o‐hydroxy group directing cyclization of isoxazole‐styrenes and Michael addition of 3,5‐dimethyl‐4‐nitroisoxazole on 2‐imino‐2H‐chromene‐3‐carbonitrile (independent methods). The developed methodology was further extended for nitromethane, malononitrile, and alkylcyanoacetates as Michael donors.

  DOI：

  10.1002/jhet.4251
• 作为产物：
  描述：

  5-硝基水杨醛 、 丙二腈 生成 2-Imino-6-nitrochromene-3-carbonitrile
  参考文献：
  名称：

  新的HA 14-1类似物：2-氨基-4-氰基-4 H-苯甲基的合成

  摘要：

  据报道，通过一种简单而有效的方法合成了2-氨基-4-氰基-4 H-色烯衍生物作为新的HA 14-1类似物。此外，2-氨基-2 H-亚甲基-3-腈，水杨醛和胺类的反应导致形成新的苯并[2,3- d ]嘧啶衍生物。

  DOI：

  10.1016/j.tetlet.2010.09.090

文献信息

• Enantioselective vinylogous Michael addition of β,γ-unsaturated butenolide to 2-iminochromenes
  作者：Vijay Gupta、Ravi P. Singh

  DOI：10.1039/c9nj01584a

  日期：——

  An efficient organocatalyzed asymmetric synthesis of 2-amino-4-(2-furanone)-4H-chromene-3-carbonitriles via vinylogous Michael addition of non-activated β,γ-unsaturated butenolide to 2-iminochromenes has been realized.

  已经实现了通过将未活化的β，γ-不饱和丁烯内酯乙烯基键合到2-亚氨基色酮上的有效的有机催化不对称合成2-氨基-4-（2-呋喃酮）-4 H-亚甲基-3-腈。
• Organocatalytic conjugate addition promoted by multi-hydrogen-bond cooperation: access to chiral 2-amino-3-nitrile-chromenes
  作者：Wenjun Li、Jiayao Huang、Jian Wang

  DOI：10.1039/c2ob27102h

  日期：——

  A new efficient enantioselective conjugate addition strategy has been disclosed to rapidly construct 2-amino-3-nitrile-chromene complexes via a multi-hydrogen-bond cooperative activation model.

  一种新型高效的对映选择性共轭加成策略已被揭示，通过多氢键协同活化模型，能够快速构建2-氨基-3-腈基色烯类化合物。
• New HA 14-1 analogues: synthesis of 2-amino-4-cyano-4H-chromenes
  作者：Leila Moafi、Somayeh Ahadi、Ayoob Bazgir

  DOI：10.1016/j.tetlet.2010.09.090

  日期：2010.12

  The synthesis of 2-amino-4-cyano-4H-chromene derivatives as new HA 14-1 analogues by a simple and efficient method is reported. In addition, the reaction of 2-amino-2H-chromene-3-carbonitriles, salicylaldehydes and amines results in the formation of new chromeno[2,3-d]pyrimidine derivatives.

  据报道，通过一种简单而有效的方法合成了2-氨基-4-氰基-4 H-色烯衍生物作为新的HA 14-1类似物。此外，2-氨基-2 H-亚甲基-3-腈，水杨醛和胺类的反应导致形成新的苯并[2,3- d ]嘧啶衍生物。
• Synthesis of <scp>4</scp> <i>H</i> ‐chromene‐isoxazole hybrids via <i>ortho</i> ‐hydroxy directing cyclization of isoxazole‐styrenes and Michael addition of imino‐chromenes in aqueous medium
  作者：Sakkani Nagaraju、Kota Sathish、Dhurke Kashinath

  DOI：10.1002/jhet.4251

  日期：2021.6

  AbstractA green, efficient, and one‐pot method synthesis of functionalized 4H‐chromene‐isoxazole hybrids is reported via o‐hydroxy group directing cyclization of isoxazole‐styrenes and Michael addition of 3,5‐dimethyl‐4‐nitroisoxazole on 2‐imino‐2H‐chromene‐3‐carbonitrile (independent methods). The developed methodology was further extended for nitromethane, malononitrile, and alkylcyanoacetates as Michael donors.
• Visible-light-induced alkylation of 2-iminochromene
  作者：Shashank Singh、Ravi P. Singh

  DOI：10.1039/d2ob01584f

  日期：——

  A metal-free, photochemical protocol for C-4 alkylation of 2-iminochromene has been developed by employing the naturally abundant feedstock carboxylic acid. Selective C-4 alkylation under photoredox conditions to access C-4 alkylated 2-iminochromene in up to 81% yield was achieved. In addition, biologically relevant chromophores can be easily incorporated under this protocol.

  通过使用天然丰富的原料羧酸，开发了一种用于 2-亚氨基色烯的 C-4 烷基化的无金属光化学方案。实现了在光氧化还原条件下的选择性 C-4 烷基化以高达 81% 的产率获得 C-4 烷基化的 2-亚氨基色烯。此外，生物相关的发色团可以很容易地纳入该协议。