(1R,3S,4S,5R,6R,7S)-3-methoxy-4-methyl-2-oxabicyclo[3.3.0]-octane | 286408-52-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 氧烷类
• 英文名称: (1R,3S,4S,5R,6R,7S)-3-methoxy-4-methyl-2-oxabicyclo[3.3.0]-octane
• 英文别名: (1R,2R,4S,6R,8S,9S)-8-methoxy-9-methyl-3,7-dioxatricyclo[4.3.0.02,4]nonane
• CAS: 286408-52-4
• 化学式: C₉H₁₄O₃
• 分子量: 170.208
• InChiKey: LTRMTIVMQNTQJH-WEHQQBAWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.9
• 重原子数：
  12
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  31
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (1R,3S,4S,5R,6R,7S)-3-methoxy-4-methyl-2-oxabicyclo[3.3.0]-octane 在 盐酸 、 copper(l) iodide 、 四丙基高钌酸铵 、 四丁基碘化铵 、 sodium hydride 、 N-甲基吗啉氧化物 作用下， 以 四氢呋喃 、 乙醚 、 二氯甲烷 、 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 72.42h， 生成 (2S,3S,4S)-2-(3R-butenyl)-3-methyl-4-[4-methoxy-benzyloxy]-cyclopentanone
  参考文献：
  名称：

  Synthesis of the C1−C9 Fragment of Callipeltoside-A

  摘要：

  The C1-C9 fragment of callipeltoside (17) was prepared in 12 steps and 7.2% overall yield from bicyclic lactone (+)-4. Key steps include a stereoselective epoxidation and further regiocontrolled nucleophilic opening of the oxirane ring to install two vicinal stereocenters (C5 and C6), and the use of bis(trimethylsilyl) peroxide and a catalytic amount of Sn(IV) chloride for the chemoselective Baeyer-Villiger oxidation of unsaturated cyclopentanone 15.

  DOI：

  10.1021/ol006003y
• 作为产物：
  描述：

  1(R),5(S),4(S)-methyl-2-oxa-bicyclo<3.3.0>oct-6-en-3-one 在 过氧乙酸 、 Dowex-50 、 sodium acetate 、 二异丁基氢化铝 作用下， 以 二氯甲烷 、 溶剂黄146 、 甲苯 为溶剂， 反应 55.0h， 生成 (1R,3S,4S,5R,6R,7S)-3-methoxy-4-methyl-2-oxabicyclo[3.3.0]-octane
  参考文献：
  名称：

  Synthesis of the C1−C9 Fragment of Callipeltoside-A

  摘要：

  The C1-C9 fragment of callipeltoside (17) was prepared in 12 steps and 7.2% overall yield from bicyclic lactone (+)-4. Key steps include a stereoselective epoxidation and further regiocontrolled nucleophilic opening of the oxirane ring to install two vicinal stereocenters (C5 and C6), and the use of bis(trimethylsilyl) peroxide and a catalytic amount of Sn(IV) chloride for the chemoselective Baeyer-Villiger oxidation of unsaturated cyclopentanone 15.

  DOI：

  10.1021/ol006003y

文献信息

• Synthesis of the C1−C9 Fragment of Callipeltoside-A
  作者：Francisco Velázquez、Horacio F. Olivo

  DOI：10.1021/ol006003y

  日期：2000.6.1

  The C1-C9 fragment of callipeltoside (17) was prepared in 12 steps and 7.2% overall yield from bicyclic lactone (+)-4. Key steps include a stereoselective epoxidation and further regiocontrolled nucleophilic opening of the oxirane ring to install two vicinal stereocenters (C5 and C6), and the use of bis(trimethylsilyl) peroxide and a catalytic amount of Sn(IV) chloride for the chemoselective Baeyer-Villiger oxidation of unsaturated cyclopentanone 15.