3-(4-chlorophenyl)-7-(3,5-dichlorophenyl)-6,8-dioxo-1-oxa-2,7-diazaspiro<4,4>-non-2-ene

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯烷类
• 英文名称: 3-(4-chlorophenyl)-7-(3,5-dichlorophenyl)-6,8-dioxo-1-oxa-2,7-diazaspiro<4,4>-non-2-ene
• 英文别名: 3-(4-Chlorophenyl)-7-(3,5-dichlorophenyl)-1-oxa-2,7-diazaspiro[4.4]non-2-ene-6,8-dione
• 化学式: C₁₈H₁₁Cl₃N₂O₃
• 分子量: 409.656
• InChiKey: LUBVKRDEXGWZGX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.1
• 重原子数：
  26
• 可旋转键数：
  2
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  59
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  4-chlorobenzaldoxime 在 chlorinating agent 、 三乙胺 作用下， 以 乙醚 、 氯仿 为溶剂， 生成 3-(4-chlorophenyl)-7-(3,5-dichlorophenyl)-6,8-dioxo-1-oxa-2,7-diazaspiro<4,4>-non-2-ene
  参考文献：
  名称：

  Regioselectivity in the 1,3-dipolar cycloaddition of nitrile oxides to N-(3,5-dichlorophenyl)itaconimide

  摘要：

  The regioselectivity of the nitrile oxide cycloaddition with 3,3-methylene-1-(3,5-dichlorophenyl)-2,5-pyrrolidindione (1) is discussed. Arylnitrile oxides add regioselectively to the carbon-carbon double bond of 1, giving exclusively spiro-isoxazolines 3a-k, whereas acetonitrile oxide gives both adducts 31 and 41. AMI calculations of the reactants and cycloadducts were performed, the regiochemistry of the cycloaddition seems to be controlled by steric effects. Reduction of 3a with NaBH4 in the presence of magnesium perchlorate at -20-degrees-C was regio- and stereoselective to yield the hydroxylactams 9a and 10a, whereas hydroxymethylisoxazoline 14a was obtained in the absence of Mg(ClO4)2.

  DOI：

  10.1007/bf00811316

文献信息

• Regioselectivity in the 1,3-dipolar cycloaddition of nitrile oxides to N-(3,5-dichlorophenyl)itaconimide
  作者：Ľ. Fišera、M. Konopíková、P. Ertl、N. Prónayová

  DOI：10.1007/bf00811316

  日期：1994.3

  The regioselectivity of the nitrile oxide cycloaddition with 3,3-methylene-1-(3,5-dichlorophenyl)-2,5-pyrrolidindione (1) is discussed. Arylnitrile oxides add regioselectively to the carbon-carbon double bond of 1, giving exclusively spiro-isoxazolines 3a-k, whereas acetonitrile oxide gives both adducts 31 and 41. AMI calculations of the reactants and cycloadducts were performed, the regiochemistry of the cycloaddition seems to be controlled by steric effects. Reduction of 3a with NaBH4 in the presence of magnesium perchlorate at -20-degrees-C was regio- and stereoselective to yield the hydroxylactams 9a and 10a, whereas hydroxymethylisoxazoline 14a was obtained in the absence of Mg(ClO4)2.