3a,4,6,6a-Tetrahydro-3-phenylfuro<3,4-d>isoxazole | 18762-53-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 氧氮杂卓类
• 英文名称: 3a,4,6,6a-Tetrahydro-3-phenylfuro<3,4-d>isoxazole
• 英文别名: 3-phenyl-(3ar,6ac)-3a,4,6,6a-tetrahydro-furo[3,4-d]isoxazole；3-Phenyl-3aξ,4,6,6aξ-tetrahydro-furo<3.4-d>isoxazol；(3aR,6aR)-3-phenyl-3a,4,6,6a-tetrahydrofuro[3,4-d][1,2]oxazole
• CAS: 18762-53-3；86761-68-4；147124-81-0
• 化学式: C₁₁H₁₁NO₂
• 分子量: 189.214
• InChiKey: KTKOPTCKLXRUOS-ZJUUUORDSA-N

物化性质

• 熔点：
  64-65 °C
• 沸点：
  304.4±52.0 °C(Predicted)
• 密度：
  1.33±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  14
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  30.8
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  3a,4,6,6a-Tetrahydro-3-phenylfuro<3,4-d>isoxazole 在 palladium on activated charcoal 、 W-2 Ra-Ni 硫酸 、 氢气 、 硼酸 作用下， 以 甲醇 、 水 为溶剂， 反应 13.0h， 生成 (3S,4S)-3-Acetoxy-4-benzyltetrahydrofuran
  参考文献：
  名称：

  Enantiocontrolled synthesis of burseran, brassilignan, dehydroxycubebin, and other tetrahydrofuran lignans in both enantiomeric forms. Application of intermolecular nitrile oxide cycloadditions and lipase-mediated kinetic resolutions

  摘要：

  Several natural and unnatural tetrahydrofuran lignans have been synthesized by a convergent approach. Our methodology utilizes a nitrile oxide cycloaddition to dihydrofuran 8 and an enzymatic resolution of alcohols 11 by lipase PS. The lipase-mediated kinetic resolution of alcohols 11 furnished both enantiomers of the lignan precursors 12 and 14 in high optical purity (>99% ee). This is followed by a S(N)2 displacement of tosylates 15 and 18 by alpha-lithiobenzyl phenyl sulfides. In this manner, both enantiomers of 3,4-dibenzyltetrahydrofuran (17a, 20a), 3,4-bis(3-methoxybenzyl)-tetrahydrofuran (17b, 20b), brassilignan (17c, 20c), dehydroxycubebin (17d, 20d), and burseran (17e, 20e) were synthesized in overall yields of 6-16%.

  DOI：

  10.1021/jo00060a037
• 作为产物：
  描述：

  2,5-二氢呋喃 、 benzohydroximoyl chloride 在 三乙胺 作用下， 以 乙醚 为溶剂， 反应 15.0h， 以84%的产率得到3a,4,6,6a-Tetrahydro-3-phenylfuro<3,4-d>isoxazole
  参考文献：
  名称：

  Enantiocontrolled synthesis of burseran, brassilignan, dehydroxycubebin, and other tetrahydrofuran lignans in both enantiomeric forms. Application of intermolecular nitrile oxide cycloadditions and lipase-mediated kinetic resolutions

  摘要：

  Several natural and unnatural tetrahydrofuran lignans have been synthesized by a convergent approach. Our methodology utilizes a nitrile oxide cycloaddition to dihydrofuran 8 and an enzymatic resolution of alcohols 11 by lipase PS. The lipase-mediated kinetic resolution of alcohols 11 furnished both enantiomers of the lignan precursors 12 and 14 in high optical purity (>99% ee). This is followed by a S(N)2 displacement of tosylates 15 and 18 by alpha-lithiobenzyl phenyl sulfides. In this manner, both enantiomers of 3,4-dibenzyltetrahydrofuran (17a, 20a), 3,4-bis(3-methoxybenzyl)-tetrahydrofuran (17b, 20b), brassilignan (17c, 20c), dehydroxycubebin (17d, 20d), and burseran (17e, 20e) were synthesized in overall yields of 6-16%.

  DOI：

  10.1021/jo00060a037

文献信息

• Adachi,I.; Kano,H., Chemical and pharmaceutical bulletin, 1968, vol. 16, # 1, p. 117 - 125
  作者：Adachi,I.、Kano,H.

  DOI：——

  日期：——
• Fisera, Lubor; Goljer, Igor; Jaroskova, Libuse, Collection of Czechoslovak Chemical Communications, 1988, vol. 53, # 8, p. 1753 - 1760
  作者：Fisera, Lubor、Goljer, Igor、Jaroskova, Libuse

  DOI：——

  日期：——
• FISERA, LUBOR;GOLJER, IGOR;JAROSKOVA, LIBUSE, COLLECT. CZECHOSL. CHEM. COMMUN., 53,(1988) N 8, C. 1753-1760
  作者：FISERA, LUBOR、GOLJER, IGOR、JAROSKOVA, LIBUSE

  DOI：——

  日期：——