3-(naphthalen-2-yl)-2H-azirine-2-carbaldehyde | 1021942-56-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 3-(naphthalen-2-yl)-2H-azirine-2-carbaldehyde
• 英文别名: 3-naphthalen-2-yl-2H-azirine-2-carbaldehyde
• CAS: 1021942-56-2
• 化学式: C₁₃H₉NO
• 分子量: 195.221
• InChiKey: PPGOOQZXXTVMLU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  15
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.08
• 拓扑面积：
  29.4
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  3-(naphthalen-2-yl)-2H-azirine-2-carbaldehyde 在 三氯化铝 作用下， 以 二氯甲烷 为溶剂， 反应 0.17h， 以75%的产率得到4-(2-萘基)恶唑
  参考文献：
  名称：

  含醛官能团的叠氮基的合成及其作为五元恶唑和异恶唑的合成工具的用途

  摘要：

  报道了一种在室温下由开链溴/氯醛合成含醛官能团的叠氮基的简单有用的方法。已经使用不同的有机金属催化剂和多种路易斯酸检查了许多3-取代的2-甲酰基-叠氮基的扩环反应的范围。

  DOI：

  10.1002/jhet.5570450203
• 作为产物：
  描述：

  2-(2-naphthyl)-3-chloroacrolein 在 sodium azide 作用下， 以 二甲基亚砜 、 甲苯 为溶剂， 反应 2.75h， 生成 3-(naphthalen-2-yl)-2H-azirine-2-carbaldehyde
  参考文献：
  名称：

  Carbene-Catalyzed [4 + 2] Annulation of 2H-Azirine-2-carboxaldehydes with Ketones via Azolium Aza-Dienolate Intermediate

  摘要：

  A new carbene-catalyzed [4 + 2] annulation of 2H-azirine-2-carbaldehydes with ketones was developed, thus providing the 2,3-dihydro-6H-1,3-oxazin-6-one core structures with broad scope and good to excellent yields. Notably, the azolium aza-dienolates generated from the addition of NHCs to 2H-azirines are first uncovered.

  DOI：

  10.1021/acs.orglett.8b03378

文献信息

• ANTICANCER 1,3-DIOXANE-4,6-DIONE DERIVATIVES AND METHOD OF COMBINATORIAL SYNTHESIS THEREOF
  申请人：National Guard Health Affairs

  公开号：US20200290975A1

  公开（公告）日：2020-09-17

  Compounds, methods of synthesis, and methods of cancer treatment by arylidene-1,3-dioxane-4,6-diones. A Meldrum's acid-based chemistry and hybrid solid-liquid method. The method includes protection of ketone and aldehyde components and simultaneous immobilization on the solid phase, introduction of substituents, grafts and derivatives compatible with the protection, detachment and restoration of active carbonyl reactivity, reaction of ketone library with malonate, reacting of the products with the aldehyde library in liquid phase and separation of the products by preparative HPLC.

  芳基亚甲基-1,3-二氧杂环己-4,6-二酮的化合物、合成方法和癌症治疗方法。基于梅尔德鲁姆酸的化学和混合固-液方法。该方法包括对酮和醛组分进行保护并同时固相固定，引入适用于保护的取代基、嫁接和衍生物，分离和恢复活性羰基反应性，将酮库与马隆酸酯反应，将产物与液相中的醛库反应，通过制备性高效液相色谱法分离产物。
• Anticancer 1,3-dioxane-4,6-dione derivatives and method of combinatorial synthesis thereof
  申请人：National Guard Health Affairs

  公开号：US11161823B2

  公开（公告）日：2021-11-02

  Compounds, methods of synthesis, and methods of cancer treatment by arylidene-1,3-dioxane-4,6-diones. A Meldrum's acid-based chemistry and hybrid solid-liquid method. The method includes protection of ketone and aldehyde components and simultaneous immobilization on the solid phase, introduction of substituents, grafts and derivatives compatible with the protection, detachment and restoration of active carbonyl reactivity, reaction of ketone library with malonate, reacting of the products with the aldehyde library in liquid phase and separation of the products by preparative HPLC.

  芳基-1,3-二恶烷-4,6-二酮的化合物、合成方法和癌症治疗方法。一种基于 Meldrum 酸的化学和固液混合法。该方法包括保护酮和醛成分并同时固定在固相上，引入与保护、分离和恢复活性羰基反应性兼容的取代基、接枝和衍生物，酮库与丙二酸酯反应，产物与液相中的醛库反应，以及通过制备型高效液相色谱分离产物。
• Synthesis of Pyrimido[1,2-<i>a</i>]indolediones and Pyrimidinediones via [4+2] Annulation of 2<i>H</i>-Azirine-2-carbaldehydes
  作者：Lesong Li、Zhenyu Shi、Congyang Li、Xiaoli Zhang、Yichi Zhang、Weiwu Ren

  DOI：10.1021/acs.joc.4c00654

  日期：——

  developed, providing straightforward synthetic protocols for constructing structurally intriguing pyrimido[1,2-a]indolediones and pyrimidinediones under mild conditions with excellent yields. This protocol can be used to synthesize the core skeleton of pharmaceutically important drugs and pyrimido[1,2-a]indoledione-containing natural products, making it potentially valuable for creating biologically

  已经开发出 NHC 催化的 2 H-氮丙啶-2-甲醛与酮亚胺和异氰酸酯的 [4+2] 成环反应，为在温和条件下构建结构有趣的嘧啶并[1,2- a ]吲哚二酮和嘧啶二酮提供了简单的合成方案，具有优异的合成性能。产量。该方案可用于合成药学上重要的药物和含嘧啶并[1,2- a ]吲哚二酮的天然产物的核心骨架，使其对于创建生物活性衍生物具有潜在价值。
• Carbene-Catalyzed [4 + 2] Annulation of 2<i>H</i>-Azirine-2-carboxaldehydes with Ketones via Azolium Aza-Dienolate Intermediate
  作者：Qiupeng Peng、Bei Zhang、Yangxi Xie、Jian Wang

  DOI：10.1021/acs.orglett.8b03378

  日期：2018.12.7

  A new carbene-catalyzed [4 + 2] annulation of 2H-azirine-2-carbaldehydes with ketones was developed, thus providing the 2,3-dihydro-6H-1,3-oxazin-6-one core structures with broad scope and good to excellent yields. Notably, the azolium aza-dienolates generated from the addition of NHCs to 2H-azirines are first uncovered.
• Synthesis of azirines containing aldehyde functionality and their utilization as synthetic tools for five membered oxazoles and isoxazoles
  作者：Sulagna Brahma、Jayanta K. Ray

  DOI：10.1002/jhet.5570450203

  日期：2008.3

  A simple and useful procedure for the synthesis of azirines containing aldehyde functionality from open chain bromo/chloro-aldehydes at room temperature is reported. The scope of the ring expansion reaction of a number of 3-substituted-2-formyl-azirines has been examined using different oraganometallic catalysts and a variety of Lewis acids.

  报道了一种在室温下由开链溴/氯醛合成含醛官能团的叠氮基的简单有用的方法。已经使用不同的有机金属催化剂和多种路易斯酸检查了许多3-取代的2-甲酰基-叠氮基的扩环反应的范围。