2,2-dimethylpenta-3,4-dienal oxime | 913260-88-5

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: 2,2-dimethylpenta-3,4-dienal oxime
• CAS: 913260-88-5
• 化学式: C₇H₁₁NO
• 分子量: 125.17
• InChiKey: FWZMAPGEWQQUQZ-UHFFFAOYSA-N

物化性质

• 沸点：
  207.4±10.0 °C(Predicted)
• 密度：
  0.83±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.3
• 重原子数：
  9
• 可旋转键数：
  2
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  32.6
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  2,2-dimethylpenta-3,4-dienal oxime 在 盐酸 、 sodium cyanoborohydride 、 sodium hydroxide 作用下， 以 甲醇 、 水 为溶剂， 反应 3.08h， 以72%的产率得到3,4-二氢-3,3,5-三甲基-2H-吡咯 1-氧化物
  参考文献：
  名称：

  Allenyloxime—a new source of heterocyclizations to stable cyclic nitrones

  摘要：

  A variety of conditions including reductive and/or basic reagents in aqueous or alcoholic solution was applied to 2,2-dimethylpenta-3,4-dienal oxime. Formation of various five-membered heterocycles with excellent chemical selectivity was observed. Most of the reactions yielded cyclic nitrones with stable dipolar structure and unique functionalities present. All products of cyclization were isolated and fully characterized. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2008.07.113
• 作为产物：
  描述：

  2,2-二甲基戊-3,4-二烯醛 在 盐酸羟胺 、 三乙胺 作用下， 以 二氯甲烷 为溶剂， 生成 2,2-dimethylpenta-3,4-dienal oxime
  参考文献：
  名称：

  2,5-双功能五元环硝基的新型多组分Domino方法

  摘要：

  研究了2,2-二甲基戊-3,4-二肟 与醛和伯醇的多组分反应，并确定了制备新的2,5-取代的五元环硝酮家族的最佳条件。该反应可在单个合成步骤中直接进入目标结构。评价了反应的范围和局限性，并对所有产物进行了分离和充分表征。 丙二烯-醇-醛-多米诺反应-多组分反应-硝酮

  DOI：

  10.1055/s-0031-1289726

文献信息

• One-pot, three-component synthesis of five-membered cyclic nitrones by addition/cyclization/condensation domino reaction
  作者：Marian Buchlovič、Stanislav Man、Konstantin Kislitsõn、Charlotte Mathot、Milan Potáček

  DOI：10.1016/j.tet.2010.01.040

  日期：2010.3

  A new approach to five-membered cyclic nitrones connected with the incorporation of a planar aromatic ring system into the structure is described. This procedure is based on an allenyloxime one-pot domino transformation under simple base catalysis in alcoholic and aqueous solvents. The structure of obtained nitrones was studied by X-ray analysis and the reactivity of products in 1,3-dipolar cycloadditions

  描述了一种新的五元环硝酮的新方法，该方法与将平面芳族环系统结合到结构中有关。该程序基于在醇和水性溶剂中简单碱催化下的烯丙基肟一锅多米诺骨牌转化。通过X射线分析研究得到的硝酮的结构，并测试产物在1，3-偶极环加成中的反应性。
• New PAH derivatives functionalized by cyclic nitrone framework: Synthetic design, anti-proliferative activity and interaction with DNA
  作者：Marian Buchlovič、Zdeněk Kříž、Ctirad Hofr、Milan Potáček

  DOI：10.1016/j.bmc.2013.01.004

  日期：2013.3

  Novel approach to functionalized polycyclic aromatic hydrocarbons (PAHs) is presented. Incorporation of cyclic nitrone framework into the structure of PAHs was studied with respect to their anti-proliferative activities and interaction with double stranded DNA. Theoretical docking studies and UV titration methods were used for preliminary evaluation of binding of new PAH derivatives to DNA structure. (C) 2013 Elsevier Ltd. All rights reserved.
• Novel Multicomponent Domino Approach to 2,5-Bifunctionalized Five-Membered Cyclic Nitrones
  作者：Milan Potáček、Marian Buchlovič、Stanislav Man

  DOI：10.1055/s-0031-1289726

  日期：2012.3

  Multicomponent reactions of 2,2-dimethylpenta-3,4-di­enal oxime with aldehydes and primary alcohols were studied and the optimum conditions for preparing a new family of 2,5-substituted five-membered cyclic nitrones were identified. This reaction offers direct access to the target structures in a single synthetic step. The scope and limitations of the reaction were evaluated, and all products were

  研究了2,2-二甲基戊-3,4-二肟 与醛和伯醇的多组分反应，并确定了制备新的2,5-取代的五元环硝酮家族的最佳条件。该反应可在单个合成步骤中直接进入目标结构。评价了反应的范围和局限性，并对所有产物进行了分离和充分表征。 丙二烯-醇-醛-多米诺反应-多组分反应-硝酮
• Allenyloxime—a new source of heterocyclizations to stable cyclic nitrones
  作者：Marian Buchlovič、Stanislav Man、Milan Potáček

  DOI：10.1016/j.tet.2008.07.113

  日期：2008.10

  A variety of conditions including reductive and/or basic reagents in aqueous or alcoholic solution was applied to 2,2-dimethylpenta-3,4-dienal oxime. Formation of various five-membered heterocycles with excellent chemical selectivity was observed. Most of the reactions yielded cyclic nitrones with stable dipolar structure and unique functionalities present. All products of cyclization were isolated and fully characterized. (C) 2008 Elsevier Ltd. All rights reserved.