(3aR,4R,6aS)-4-(1-menthyloxy)-3-methyl-3a,6a-dihydrofuro[3,4-d]isoxazol-6-(4H)-one N-oxide | 646066-05-9

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 异戊烯醇脂质
• 英文名称: (3aR,4R,6aS)-4-(1-menthyloxy)-3-methyl-3a,6a-dihydrofuro[3,4-d]isoxazol-6-(4H)-one N-oxide
• 英文别名: (3aR,4R,6aS)-3-methyl-4-[(1R,2S,5R)-5-methyl-2-propan-2-ylcyclohexyl]oxy-2-oxido-4,6a-dihydro-3aH-furo[3,4-d][1,2]oxazol-2-ium-6-one
• CAS: 646066-05-9
• 化学式: C₁₆H₂₅NO₅
• 分子量: 311.378
• InChiKey: NIHPJIXYHNSYCX-PJOFYZRYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  22
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.88
• 拓扑面积：
  73.5
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (3aR,4R,6aS)-4-(1-menthyloxy)-3-methyl-3a,6a-dihydrofuro[3,4-d]isoxazol-6-(4H)-one N-oxide 在 palladium on activated charcoal 氢气 作用下， 以 乙酸乙酯 为溶剂， 20.0 ℃ 、101.32 kPa 条件下， 反应 24.0h， 以90%的产率得到(3aR,4R,6aS)-4-(1-menthyloxy)-3-methyl-3a,6a-dihydrofuro[3,4-d]isoxazol-6-(4H)-one
  参考文献：
  名称：

  MIRC reactions of 2-bromo-5-(l-menthyloxy)furan-2(5H)-one with stabilized anions. Preparation of homochiral bicyclic γ-butyrolactones

  摘要：

  Homochiral (SR)-4-bromo-5-(l-menthyloxy)furan-2(5H)-one with stabilized carbanions (from nitroalkanes, malononitrile and ethyl acetoacetate) afforded enantiopure bicyclic compounds in good yield (70-90%). 3-Oxabicyclic[3. 1.0]hexan-2-one derivatives were obtained with nitromethane and malonic acid derivatives. However, dihydrofuro[3,4-d]isoxazol-6-one and dihydrofuro[3,4-b]furan-6(4H)-one derivatives were obtained from nitroethane and ethyl acetoacetate, respectively. (C) 1999 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(99)00378-x
• 作为产物：
  描述：

  (5S)-3-bromo-5-(1-methyloxy)furan-2(5H)-one 在 对甲苯磺酸 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 作用下， 以 四氢呋喃 、 甲苯 为溶剂， 反应 0.5h， 生成 (3aR,4R,6aS)-4-(1-menthyloxy)-3-methyl-3a,6a-dihydrofuro[3,4-d]isoxazol-6-(4H)-one N-oxide
  参考文献：
  名称：

  MIRC reactions of 2-bromo-5-(l-menthyloxy)furan-2(5H)-one with stabilized anions. Preparation of homochiral bicyclic γ-butyrolactones

  摘要：

  Homochiral (SR)-4-bromo-5-(l-menthyloxy)furan-2(5H)-one with stabilized carbanions (from nitroalkanes, malononitrile and ethyl acetoacetate) afforded enantiopure bicyclic compounds in good yield (70-90%). 3-Oxabicyclic[3. 1.0]hexan-2-one derivatives were obtained with nitromethane and malonic acid derivatives. However, dihydrofuro[3,4-d]isoxazol-6-one and dihydrofuro[3,4-b]furan-6(4H)-one derivatives were obtained from nitroethane and ethyl acetoacetate, respectively. (C) 1999 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(99)00378-x

文献信息

• MIRC reactions of 2-bromo-5-(l-menthyloxy)furan-2(5H)-one with stabilized anions. Preparation of homochiral bicyclic γ-butyrolactones
  作者：M.Carmen Maestro、M.Cruz Barquilla、M.Rosario Martı́n

  DOI：10.1016/s0957-4166(99)00378-x

  日期：1999.9

  Homochiral (SR)-4-bromo-5-(l-menthyloxy)furan-2(5H)-one with stabilized carbanions (from nitroalkanes, malononitrile and ethyl acetoacetate) afforded enantiopure bicyclic compounds in good yield (70-90%). 3-Oxabicyclic[3. 1.0]hexan-2-one derivatives were obtained with nitromethane and malonic acid derivatives. However, dihydrofuro[3,4-d]isoxazol-6-one and dihydrofuro[3,4-b]furan-6(4H)-one derivatives were obtained from nitroethane and ethyl acetoacetate, respectively. (C) 1999 Elsevier Science Ltd. All rights reserved.