5-butyl-3-(4-methoxyphenyl)-2-isoxazoline | 70416-62-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: 5-butyl-3-(4-methoxyphenyl)-2-isoxazoline
• 英文别名: 5-butyl-3-(4-methoxy-phenyl)-4,5-dihydro-isoxazole；5-Butyl-3-(4-methoxyphenyl)-4,5-dihydro-1,2-oxazole
• CAS: 70416-62-5
• 化学式: C₁₄H₁₉NO₂
• 分子量: 233.31
• InChiKey: GBJHORCAWDETCU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  17
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  30.8
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  1-己烯 、 3,4-bis(4-methoxyphenyl)-1,2,5-oxadiazole-2-oxide 生成 5-butyl-3-(4-methoxyphenyl)-2-isoxazoline
  参考文献：
  名称：

  从呋喃山氧化物的热裂解中分离出腈类氧化物

  摘要：

  呋喃喃的闪蒸真空热解生成一氧化氮，该氧化氮已与烯烃反应生成2-异恶唑啉，并已通过1 H和13 C nmr光谱进行了检查。

  DOI：

  10.1016/s0040-4039(01)86315-2

文献信息

• Flash vacuum pyrolysis of 1,2,5-oxadiazole 2-oxides and 1,2,3-triazole 1-oxides
  作者：William R. Mitchell、R. Michael Paton

  DOI：10.3998/ark.5550190.0011.a04

  日期：——

  The flash vacuum pyrolysis (FVP, 450-600 oC/10 -3 mmHg) of 3,4-diaryl- and 3,4-dialkyl-1,2,5oxadiazole 2-oxides (furoxans) has been investigated. In all cases the 1,2,5-oxadiazole ring cleaved cleanly at O(1)-N(2) and C(3)-C(4) to afford two nitrile oxide fragments, which were trapped in high yield (75-97%) as their isoxazoline cycloadducts by reaction with alk-1-enes. At higher temperatures (700-800

  已经研究了 3,4-二芳基和 3,4-二烷基-1,2,5 恶二唑 2-氧化物（呋喃烷）的快速真空热解（FVP，450-600 oC/10 -3 mmHg）。在所有情况下，1,2,5-恶二唑环在 O(1)-N(2) 和 C(3)-C(4) 处完全裂解，得到两个腈氧化物片段，它们以高产率 (75- 97%) 作为它们的异恶唑啉环加合物与 1-烯烃反应。在更高的温度 (700-800 oC) 下，异氰酸酯会作为副产物形成。乙腈氧化物二聚化成二甲基呋喃后进行 1 H NMR 光谱，并确定二阶反应的速率常数。呋喃烷通过 FVP 以良好的产率 (61-95%) 转化为异氰酸酯，然后二氧化硫介导的生成腈氧化物的异构化。2,4,5-三取代-1,2,3-三唑1-氧化物表现出更高的热稳定性，但在 700-800 oC 下，4,5-二甲基化合物 25b 分解生成 1,2-二（5-甲基-2-苯基 1,2,3-三唑
• 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.