(1S,3R,4R)-3-Hydroxy-7,7-dimethoxy-bicyclo[2.2.1]heptan-2-one oxime | 350995-94-7

• 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: (1S,3R,4R)-3-Hydroxy-7,7-dimethoxy-bicyclo[2.2.1]heptan-2-one oxime
• CAS: 350995-94-7
• 化学式: C₉H₁₅NO₄
• 分子量: 201.222
• InChiKey: LXCPRQTUHNQZPQ-SHYZEUOFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.21
• 重原子数：
  14.0
• 可旋转键数：
  2.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.89
• 拓扑面积：
  71.28
• 氢给体数：
  2.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  (1S,3R,4R)-3-Hydroxy-7,7-dimethoxy-bicyclo[2.2.1]heptan-2-one oxime 在 sodium tetrahydroborate 、 sodium 、 nickel dichloride 作用下， 以 甲醇 为溶剂， 反应 7.5h， 生成 (-)-3-exo-amino-7,7-dimethoxynorbornan-2-exo-ol
  参考文献：
  名称：

  An efficient synthesis of enantiopure (+)- and (−)-3-exo-amino-7,7-dimethoxynorbornan-2-exo-ols

  摘要：

  We describe the synthesis of new amino alcohols (+)- and (-)-3-exo-amino-7,7-dimethoxynorbonan-2-exo-ols. The (+)or (-)-7,7-dimethoxy-1,4,5,6-tetrachlorobicyclo[2.2.1]hept-5-en-2-endo-ol, obtained from the enzyme catalysed transesterification of the racemate, was reduced and dechlorinated (Na/NH3; ethanol), followed by pyridinium chlorochromate oxidation of the resultant alcohols to the corresponding ketones. After treatment with t-BuOK/BuONO, in a nitrosation reaction, alpha -keto oximes were obtained. Reduction over two steps with NaBH4 and NaBH4/NiCl2. 6H(2)O followed by in situ acetylation furnished the corresponding acetamido esters, which were hydrolysed with CH3OH/Na to produce the enantiopure amino alcohols in good yields. (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(01)00085-4
• 作为产物：
  描述：

  (1RS,2RS,4SR)-7,7-dimethoxybicyclo[2.2.1]heptan-2-ol 在 sodium tetrahydroborate 、 亚硝酸丁酯 、 potassium tert-butylate 、 pyridinium chlorochromate 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 为溶剂， 生成 (1S,3R,4R)-3-Hydroxy-7,7-dimethoxy-bicyclo[2.2.1]heptan-2-one oxime
  参考文献：
  名称：

  An efficient synthesis of enantiopure (+)- and (−)-3-exo-amino-7,7-dimethoxynorbornan-2-exo-ols

  摘要：

  We describe the synthesis of new amino alcohols (+)- and (-)-3-exo-amino-7,7-dimethoxynorbonan-2-exo-ols. The (+)or (-)-7,7-dimethoxy-1,4,5,6-tetrachlorobicyclo[2.2.1]hept-5-en-2-endo-ol, obtained from the enzyme catalysed transesterification of the racemate, was reduced and dechlorinated (Na/NH3; ethanol), followed by pyridinium chlorochromate oxidation of the resultant alcohols to the corresponding ketones. After treatment with t-BuOK/BuONO, in a nitrosation reaction, alpha -keto oximes were obtained. Reduction over two steps with NaBH4 and NaBH4/NiCl2. 6H(2)O followed by in situ acetylation furnished the corresponding acetamido esters, which were hydrolysed with CH3OH/Na to produce the enantiopure amino alcohols in good yields. (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(01)00085-4