(1E,2E)-2-methyl-3-phenylacrylaldehyde dimethyldrazone

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: (1E,2E)-2-methyl-3-phenylacrylaldehyde dimethyldrazone
• 英文别名: N,N-dimethyl-N'-(2-methyl-3-phenylallylidene)hydrazine；2-Methyl-3-phenyl-2-propenal-dimethylhydrazon；N-methyl-N-[(E)-[(E)-2-methyl-3-phenylprop-2-enylidene]amino]methanamine
• 化学式: C₁₂H₁₆N₂
• 分子量: 188.272
• InChiKey: CCOWJEAZUMDZGC-HOJJKJLFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  14
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  15.6
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (1E,2E)-2-methyl-3-phenylacrylaldehyde dimethyldrazone 在 盐酸 、 (乙腈)[(2-联苯)二叔丁基膦]六氟锑酸金(I) 作用下， 以 乙醚 、 水 、 1,2-二氯乙烷 为溶剂， 反应 3.58h， 生成 (1R,4R,Z)-1-methyl-2-((2-oxooxazolidin-3-yl)methylene)-4-phenylcyclobutane-1-carbaldehyde
  参考文献：
  名称：

  Gold(I)-Catalyzed Intermolecular Cycloaddition of Allenamides with α,β-Unsaturated Hydrazones: Efficient Access to Highly Substituted Cyclobutanes

  摘要：

  alpha,beta-Unsaturated N,N-dialkyl hydrazones undergo a mild [2 + 2] cycloaddition to allenamides when treated with a suitable gold catalyst. The method, which represents the first application of N,N-dialkyl hydrazones in gold catalysis, is compatible with a wide variety of substituents at the alkenyl moiety of the hydrazone component, proceeds with excellent levels of regio- and diastereoselectivity, and provides densely substituted cyclobutanes with good to excellent yields.

  DOI：

  10.1021/ol503121q
• 作为产物：
  描述：

  (E)-2-methyl-3-phenylacrylaldehyde 、 偏二甲肼 在 magnesium sulfate 作用下， 以 二氯甲烷 为溶剂， 反应 24.0h， 以74%的产率得到(1E,2E)-2-methyl-3-phenylacrylaldehyde dimethyldrazone
  参考文献：
  名称：

  Gold(I)-Catalyzed Intermolecular Cycloaddition of Allenamides with α,β-Unsaturated Hydrazones: Efficient Access to Highly Substituted Cyclobutanes

  摘要：

  alpha,beta-Unsaturated N,N-dialkyl hydrazones undergo a mild [2 + 2] cycloaddition to allenamides when treated with a suitable gold catalyst. The method, which represents the first application of N,N-dialkyl hydrazones in gold catalysis, is compatible with a wide variety of substituents at the alkenyl moiety of the hydrazone component, proceeds with excellent levels of regio- and diastereoselectivity, and provides densely substituted cyclobutanes with good to excellent yields.

  DOI：

  10.1021/ol503121q

文献信息

• [4 + 2]-Cycloadditionen von ?,?-unges�ttigten Hydrazonen. Teil 1. Pyridin-2,3-dicarboximide aus 1-(Dimethylamino)-1,4-dihydropyridin-Derivaten
  作者：Adrian Waldner

  DOI：10.1002/hlca.19880710222

  日期：1988.3.16

  [4 + 2] Cycloadditions of α,β-Unsaturated Hydrazones to Pyridine-2,3-dicarboximides via 1-(Dimethylamino)-1,4-dihydropyridine Derivatives

  [4 + 2]通过1-（二甲氨基）-1,4-二氢吡啶衍生物将α，β-不饱和Hy与吡啶-2,3-二羧酸二甲酰亚胺成环加成反应
• The synthesis of highly functionalised pyridines using Ghosez-type reactions of dihydropyrazoles
  作者：Federica Catti、Paula S. Kiuru、Alexandra M.Z. Slawin、Nicholas J. Westwood

  DOI：10.1016/j.tet.2008.07.063

  日期：2008.9

  The aza-Diels-Alder reaction of alpha beta-unsaturated hydrazones is a general methodology that has been applied both to the synthesis of natural products and to the development of multicomponent reactions. Trends have emerged as to the effect of substituents on the efficiency of this reaction with substituents at the C2 and C4-positions of the aza-diene in general suppressing the reaction. Here we report that 4,5-dihydropyrazoles can function as substrates in this process despite the presence of substituents at both of these positions. A one pot, four chemical step sequence carried out under standard thermal or microwave conditions results in the formation of the corresponding pyridine-containing compounds. The scope of the reaction is explored and additional insights into the proposed mechanism of this reaction are provided. (C) 2008 Elsevier Ltd. All rights reserved.
• WALDNER, ADRIAN, HELV. CHIM. ACTA, 71,(1988) N 2, 486-492
  作者：WALDNER, ADRIAN

  DOI：——

  日期：——
• Gold(I)-Catalyzed Intermolecular Cycloaddition of Allenamides with α,β-Unsaturated Hydrazones: Efficient Access to Highly Substituted Cyclobutanes
  作者：Paloma Bernal-Albert、Hélio Faustino、Ana Gimeno、Gregorio Asensio、José L. Mascareñas、Fernando López

  DOI：10.1021/ol503121q

  日期：2014.12.5

  alpha,beta-Unsaturated N,N-dialkyl hydrazones undergo a mild [2 + 2] cycloaddition to allenamides when treated with a suitable gold catalyst. The method, which represents the first application of N,N-dialkyl hydrazones in gold catalysis, is compatible with a wide variety of substituents at the alkenyl moiety of the hydrazone component, proceeds with excellent levels of regio- and diastereoselectivity, and provides densely substituted cyclobutanes with good to excellent yields.