5-(1-benzenesulfonyl-3-hydroxycyclobutyl)-3-(4-methoxyphenyl)-4,5-dihydroisoxazole | 409112-80-7

• 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: 5-(1-benzenesulfonyl-3-hydroxycyclobutyl)-3-(4-methoxyphenyl)-4,5-dihydroisoxazole
• 英文别名: 3-benzenesulfonyl-3-[3-(4-methoxyphenyl)-4,5-dihydroisoxazol-5-yl]cyclobutanol；3-(Benzenesulfonyl)-3-[3-(4-methoxyphenyl)-4,5-dihydro-1,2-oxazol-5-yl]cyclobutan-1-ol
• CAS: 409112-80-7
• 化学式: C₂₀H₂₁NO₅S
• 分子量: 387.456
• InChiKey: NGXZPAGBEGNKCJ-UHFFFAOYSA-N

物化性质

• 沸点：
  596.8±60.0 °C(Predicted)
• 密度：
  1.38±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  27
• 可旋转键数：
  5
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.35
• 拓扑面积：
  93.6
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  5-(1-benzenesulfonyl-3-hydroxycyclobutyl)-3-(4-methoxyphenyl)-4,5-dihydroisoxazole 在 氢氧化钾 、 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 为溶剂， 反应 4.0h， 生成 3,8-bis-(4-chlorophenyl)-6-[3-(4-methoxyphenyl)isoxazol-5-yl]-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
• 作为产物：
  描述：

  烯丙基苯砜 在 sodium hypochlorite 、 正丁基锂 作用下， 以 四氢呋喃 、 二氯甲烷 、 水 为溶剂， 反应 13.0h， 生成 5-(1-benzenesulfonyl-3-hydroxycyclobutyl)-3-(4-methoxyphenyl)-4,5-dihydroisoxazole
  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

• Solid-Phase Synthesis of Novel Isoxazolocyclobutanones and Isoxazolinocyclobutenones
  作者：Wei-Chieh Cheng、Melissa Wong、Marilyn M. Olmstead、Mark J. Kurth

  DOI：10.1021/ol017194n

  日期：2002.3.1

  [GRAPHICS]The preparation of novel isoxazolocyclobutanone and isoxazolinocyclobutenone derivatives via a traceless solid-phase sulfone linker strategy is described. Key steps in the solid-phase protocol reported here include (1) sulfinate --> sulfone alkylation, (11) four-member ring formation by sulfone dianion alkylation, (iii) heterocycle formation by nitrile oxide 1,3-dipolar cycloaddition, and (iv) traceless product release by cyclobutanol --> cyclobutanone oxidation with concomitant linker cleavage by sulfinate elimination.
• 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.