6-[3-(4-methoxyphenyl)isoxazol-5-yl]-3,8-diphenyl-6,7-dihydro-5H-[1,2]diazocin-4-one

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 二芳基庚烷
• 英文名称: 6-[3-(4-methoxyphenyl)isoxazol-5-yl]-3,8-diphenyl-6,7-dihydro-5H-[1,2]diazocin-4-one
• 英文别名: (1Z,2E)-5-[3-(4-methoxyphenyl)-1,2-oxazol-5-yl]-3,8-diphenyl-5,6-dihydro-4H-diazocin-7-one
• 化学式: C₂₈H₂₃N₃O₃
• 分子量: 449.509
• InChiKey: REGMMRUYFNLEDM-BBDPAYFJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.6
• 重原子数：
  34
• 可旋转键数：
  5
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.14
• 拓扑面积：
  77
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  对甲氧基苯甲醛肟 在 氢氧化钾 、 sodium hypochlorite 、 草酰氯 、 二甲基亚砜 、 三乙胺 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 、 水 为溶剂， 反应 4.0h， 生成 6-[3-(4-methoxyphenyl)isoxazol-5-yl]-3,8-diphenyl-6,7-dihydro-5H-[1,2]diazocin-4-one
  参考文献：
  名称：

  Diazocinones:  Synthesis and Conformational Analysis

  摘要：

  1,2,4,5-Tetrazines (prepared from aryl nitriles) condense with isoxazolylcyclobutanones (prepared from 3-benzenesulfonyl-3-vinylcyclobutanol) in methanolic KOH to give conformationally restricted 6-isoxazol-5-yl-6,7-dihydro-5H-[1,2]diazocin-4-ones. The solution H-1 NMR spectra of dihydrodiazocinone la with phenyl moieties at C3 and C8 reveal two conformations of the eight-membered heterocycle that are non-interconverting on the NMR time scale at ambient temperature. The kinetics of the conversion process, followed by H-1 NMR between 21 and 70 degrees C in DMSO Solution. yield an activation energy of similar to 21 kcal/mol relative to the kinetic conformer and show an equilibrated ratio of similar to 5:1 of the thermodynamic to the kinetic conformers. The electronic structure calculations on a model dihydrodiazocinone predict geometries for the two conformations. One of these geometries agrees with the X-ray crystallographic analysis of the thermodynamic conformation of 1a.

  DOI：

  10.1021/jo052577a

文献信息

• Diazocinones:  Synthesis and Conformational Analysis
  作者：Lori I. Robins、Richard D. Carpenter、James C. Fettinger、Makhluf J. Haddadin、Dino S. Tinti、Mark J. Kurth

  DOI：10.1021/jo052577a

  日期：2006.3.1

  1,2,4,5-Tetrazines (prepared from aryl nitriles) condense with isoxazolylcyclobutanones (prepared from 3-benzenesulfonyl-3-vinylcyclobutanol) in methanolic KOH to give conformationally restricted 6-isoxazol-5-yl-6,7-dihydro-5H-[1,2]diazocin-4-ones. The solution H-1 NMR spectra of dihydrodiazocinone la with phenyl moieties at C3 and C8 reveal two conformations of the eight-membered heterocycle that are non-interconverting on the NMR time scale at ambient temperature. The kinetics of the conversion process, followed by H-1 NMR between 21 and 70 degrees C in DMSO Solution. yield an activation energy of similar to 21 kcal/mol relative to the kinetic conformer and show an equilibrated ratio of similar to 5:1 of the thermodynamic to the kinetic conformers. The electronic structure calculations on a model dihydrodiazocinone predict geometries for the two conformations. One of these geometries agrees with the X-ray crystallographic analysis of the thermodynamic conformation of 1a.