3-(5-butyl-4,5-dihydroisoxazol-3-yl)benzonitrile | 1061567-79-0

• 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-(5-butyl-4,5-dihydroisoxazol-3-yl)benzonitrile
• 英文别名: 3-(5-Butyl-4,5-dihydro-1,2-oxazol-3-yl)benzonitrile
• CAS: 1061567-79-0
• 化学式: C₁₄H₁₆N₂O
• 分子量: 228.294
• InChiKey: UNGFKNNBLXQMAF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  17
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  45.4
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  呋喃 、 3-(5-butyl-4,5-dihydroisoxazol-3-yl)benzonitrile 以 乙腈 为溶剂， 以48%的产率得到(2SR,6SR,7SR,9SR)-9-butyl-7-(3-cyanophenyl)-3,10-dioxa-1-azatricyclo[5.3.0.0(2,6)]dec-4-ene
  参考文献：
  名称：

  Regio- and Stereochemistry of [2 + 2] Photocycloadditions of Imines to Alkenes: A Computational and Experimental Study

  摘要：

  The [2 + 2] photocycloaddition of isoxazolines to alkenes has been studied by means of CASPT2/6-31G*//CASSCF/6-31G*. The reaction outcome is influenced by the relative ratio of imine deactivation and photocycloaddition. Analysis of the conical intersection points involved in the photoreaction shows that fast deactivation is prevented when an electron-withdrawing group is placed in any position that can affect the imine moiety. Computational data predict that the photoreaction will be regiospecific but without stereoselectivity. Furthermore, the favored regioisomer will be different for alkenes with electron-withdrawing or electron-releasing substituents. The results of a complementary experimental study correlate well with the computational data. Several conclusions included in the present work could prove useful for the generalization of the photocycloaddition of imines.

  DOI：

  10.1021/jo8015242
• 作为产物：
  描述：

  1-己烯 、 3-cyanobenzaldehyde oxime 在 吡啶 、 N-氯代丁二酰亚胺 作用下， 以46%的产率得到3-(5-butyl-4,5-dihydroisoxazol-3-yl)benzonitrile
  参考文献：
  名称：

  Regio- and Stereochemistry of [2 + 2] Photocycloadditions of Imines to Alkenes: A Computational and Experimental Study

  摘要：

  The [2 + 2] photocycloaddition of isoxazolines to alkenes has been studied by means of CASPT2/6-31G*//CASSCF/6-31G*. The reaction outcome is influenced by the relative ratio of imine deactivation and photocycloaddition. Analysis of the conical intersection points involved in the photoreaction shows that fast deactivation is prevented when an electron-withdrawing group is placed in any position that can affect the imine moiety. Computational data predict that the photoreaction will be regiospecific but without stereoselectivity. Furthermore, the favored regioisomer will be different for alkenes with electron-withdrawing or electron-releasing substituents. The results of a complementary experimental study correlate well with the computational data. Several conclusions included in the present work could prove useful for the generalization of the photocycloaddition of imines.

  DOI：

  10.1021/jo8015242

文献信息

• Regio- and Stereochemistry of [2 + 2] Photocycloadditions of Imines to Alkenes: A Computational and Experimental Study
  作者：Diego Sampedro、Alberto Soldevilla、Pedro J. Campos、Roberto Ruiz、Miguel A. Rodríguez

  DOI：10.1021/jo8015242

  日期：2008.11.7

  The [2 + 2] photocycloaddition of isoxazolines to alkenes has been studied by means of CASPT2/6-31G*//CASSCF/6-31G*. The reaction outcome is influenced by the relative ratio of imine deactivation and photocycloaddition. Analysis of the conical intersection points involved in the photoreaction shows that fast deactivation is prevented when an electron-withdrawing group is placed in any position that can affect the imine moiety. Computational data predict that the photoreaction will be regiospecific but without stereoselectivity. Furthermore, the favored regioisomer will be different for alkenes with electron-withdrawing or electron-releasing substituents. The results of a complementary experimental study correlate well with the computational data. Several conclusions included in the present work could prove useful for the generalization of the photocycloaddition of imines.