3-methoxy-4-[(5-phenylisoxazol-3-yl)methoxy]benzaldehyde

• 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: 3-methoxy-4-[(5-phenylisoxazol-3-yl)methoxy]benzaldehyde
• 英文别名: 3-Methoxy-4-[(5-phenylisoxazol-3-yl)-methoxy]-benzaldehyde；3-methoxy-4-[(5-phenyl-1,2-oxazol-3-yl)methoxy]benzaldehyde
• 化学式: C₁₈H₁₅NO₄
• 分子量: 309.321
• InChiKey: ULOFCNPCNCWFDK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  23
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.11
• 拓扑面积：
  61.6
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (acetylcyclopentadienyl)tricarbonylmanganese 、 3-methoxy-4-[(5-phenylisoxazol-3-yl)methoxy]benzaldehyde 在 potassium hydroxide 作用下， 以 乙醇 为溶剂， 反应 4.0h， 以44%的产率得到1-cymantrenyl-3-{3-methoxy-4-[(5-phenyl-1,2-oxazol-3-yl)methoxy]phenyl}prop-2-en-1-one
  参考文献：
  名称：

  Synthesis of Azaheterocyclic Cymantrene Derivatives

  摘要：

  The reduction of acetylcymantrene with sodium tetrahydridoborate gave cymantrenylethanol which was acylated with 4,5-dichloroisothiazole- and 5-(4-methylphenyl)isoxazole-3-carbonyl chlorides to obtain esters containing a 1,2-thia(oxa)zole fragment. The condensation of acetylcymantrene with 5-arylisoxazole-3- carbaldehydes, (5-arylisoxazol-3-yl)methoxybenzaldehydes (Ar = Ph, 4-Tol), and 4,5-dichloroisothiazole-3- carbaldehyde afforded the corresponding (E)-3-(azol-3-yl)-1-cymantrenylprop-2-en-1-ones. The resulting alpha,beta- unsaturated ketones reacted with semicarbazide hydrochloride and thiosemicarbazide to produce substituted 4,5-dihydro-1H-pyrazole-1-carboxamides and -1-carbothioamides, and their reaction with hydroxylamine hydrochloride led to the formation of 4,5-dihydroisoxazoles containing cymantrene and 1,2-azole fragments. Heterocyclization of azolylcymantrenylpropenones with guanidine gave 2-aminopyrimidine derivatives, and dihydropyrimidine-2-thiones were obtained by their reaction with thiourea.

  DOI：

  10.1134/s1070428018030132
• 作为产物：
  描述：

  (5-苯基异噁唑-3-基)甲醇 在 氯化亚砜 、 potassium carbonate 作用下， 以 乙醇 、 二氯甲烷 为溶剂， 反应 126.0h， 生成 3-methoxy-4-[(5-phenylisoxazol-3-yl)methoxy]benzaldehyde
  参考文献：
  名称：

  Synthesis of functional isoxazole derivatives proceeding from (5-arylisoxazol-3-yl)chloromethanes

  摘要：

  Reaction of 3-chloromethyl-5-phenyl(p-tolyl)isoxazoles with substituted phenols under the conditions of Williamson reaction afforded the corresponding 3-aryloxymethyl-5-phenyl(p-tolyl)isoxazoles. Treating the latter with sodium methylate, sodium phenyl(benzyl, furfuryl)thiolates and morpholine in methanol resulted in the replacement of the chlorine atom in 3-chloromethyl-5-phenyl(p-tolyl)isoxazoles by methoxy-, phenyl-(benzyl, furfuryl)sulfanyl groups and morpholine residue.

  DOI：

  10.1134/s1070428015080102

文献信息

• Synthesis of Alkaloid Analogs Containing Isoxazole and Isothiazole Fragments
  作者：S. K. Petkevich、A. V. Kletskov、A. P. Kadutskii、E. A. Dikusar、N. G. Kozlov、V. I. Potkin

  DOI：10.1134/s1070428018120126

  日期：2018.12

  Three-component cascade cyclocondensation of naphthalen-2-amine with cyclic -dicarbonyl compounds and isoxazole- or isothiazolecarbaldehydes afforded new structural analogs of alkaloids containing isoxazole and isothiazole fragments.
• Synthesis of functional isoxazole derivatives proceeding from (5-arylisoxazol-3-yl)chloromethanes
  作者：V. I. Potkin、N. A. Bumagin、S. K. Petkevich、E. A. Dikusar、E. V. Semenova、P. V. Kurman、R. M. Zolotar’、S. G. Pashkevich、T. A. Gurinovich、V. A. Kul’chitskii

  DOI：10.1134/s1070428015080102

  日期：2015.8

  Reaction of 3-chloromethyl-5-phenyl(p-tolyl)isoxazoles with substituted phenols under the conditions of Williamson reaction afforded the corresponding 3-aryloxymethyl-5-phenyl(p-tolyl)isoxazoles. Treating the latter with sodium methylate, sodium phenyl(benzyl, furfuryl)thiolates and morpholine in methanol resulted in the replacement of the chlorine atom in 3-chloromethyl-5-phenyl(p-tolyl)isoxazoles by methoxy-, phenyl-(benzyl, furfuryl)sulfanyl groups and morpholine residue.
• Synthesis of Azaheterocyclic Cymantrene Derivatives
  作者：V. I. Potkin、S. K. Petkevich、A. V. Kletskov、I. A. Kolesnik、E. A. Dikusar、I. B. Rozentsveig、G. G. Levkovskaya、D. K. Nasirova、K. K. Borisova、F. I. Zubkov

  DOI：10.1134/s1070428018030132

  日期：2018.3

  The reduction of acetylcymantrene with sodium tetrahydridoborate gave cymantrenylethanol which was acylated with 4,5-dichloroisothiazole- and 5-(4-methylphenyl)isoxazole-3-carbonyl chlorides to obtain esters containing a 1,2-thia(oxa)zole fragment. The condensation of acetylcymantrene with 5-arylisoxazole-3- carbaldehydes, (5-arylisoxazol-3-yl)methoxybenzaldehydes (Ar = Ph, 4-Tol), and 4,5-dichloroisothiazole-3- carbaldehyde afforded the corresponding (E)-3-(azol-3-yl)-1-cymantrenylprop-2-en-1-ones. The resulting alpha,beta- unsaturated ketones reacted with semicarbazide hydrochloride and thiosemicarbazide to produce substituted 4,5-dihydro-1H-pyrazole-1-carboxamides and -1-carbothioamides, and their reaction with hydroxylamine hydrochloride led to the formation of 4,5-dihydroisoxazoles containing cymantrene and 1,2-azole fragments. Heterocyclization of azolylcymantrenylpropenones with guanidine gave 2-aminopyrimidine derivatives, and dihydropyrimidine-2-thiones were obtained by their reaction with thiourea.