4-metoxi-3-oxabiciclo<3.1.0>hexan-2-ona | 157826-47-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 内酯类
• 英文名称: 4-metoxi-3-oxabiciclo<3.1.0>hexan-2-ona
• 英文别名: 4-methoxy-2-oxo-1-oxabicyclo<3.1.0>hexane
• CAS: 157826-47-6
• 化学式: C₆H₈O₃
• 分子量: 128.128
• InChiKey: OFBYOMFKMRNUMX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.15
• 重原子数：
  9.0
• 可旋转键数：
  1.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.83
• 拓扑面积：
  35.53
• 氢给体数：
  0.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  4-metoxi-3-oxabiciclo<3.1.0>hexan-2-ona 在 水 作用下， 反应 4.0h， 生成 4-hidroxi-3-oxabiciclo<3.1.0>hexan-2-ona
  参考文献：
  名称：

  Farina, F.; Martin, M. V.; Soria, M. L., Anales de Quimica, 1995, vol. 91, # 1-2, p. 65 - 73

  摘要：

  DOI：
• 作为产物：
  描述：

  3,4-diaza-6-methoxy-1-oxa-2-oxo-bicyclo<3.3.0>octene 在 二苯甲酮 作用下， 以 二氯甲烷 为溶剂， 反应 2.0h， 生成 5-甲氧基呋喃-2(5h)-酮 、 4-metoxi-3-oxabiciclo<3.1.0>hexan-2-ona
  参考文献：
  名称：

  Asymmetric 1,3-dipolar cycloadditions to 5-(R)-menthyloxy-2(5H)-furanone

  摘要：

  Various diazo compounds, nitrile oxides, nitrones and azomethine ylides were examined in 1,3-dipolar cycloadditions to enantiomerically pure 5-(R)-menthyloxy-2(5H)-furanone 1a. Pyrazoline 9 was obtained in 100% c.y. as a mixture of 2 diastereoisomers in ratios up to 72 : 28, whereas pyrazoline 16 was obtained in 100% c.y. as a single enantiomer. Photochemically pyrazolines 9 and 10 have been converted to cyclopropanes 11 and 13. Under thermal conditions pyrazoline 9 is converted to 4-methyl-5-menthyloxy-2(5H)-furanone. Isoxazoles 21a-24a were obtained enantiomerically pure via nitrile oxide addition to la in 64-67% yield. Nitrone addition afforded isoxazolidines 27, 28 and 34 with complete anti-facial- and regiochemistry, but with endo-exo selectivities up to 76%. Enantiomerically pure isoxazolidines were obtained in 25-75% yield. Pyrrolidine 36 was obtained diastereomerically pure in 81% c.y. Pyrrolidines 42 and 45, however, were obtained as diastereomeric mixtures in 37% resp. 6% yield.

  DOI：

  10.1016/0957-4166(94)80023-5