4,4-Dimethoxy-2-methyl-3-oxo-butyric acid (1S,2S,3R,4S)-4,7,7-trimethyl-3-naphthalen-2-yl-bicyclo[2.2.1]hept-2-yl ester | 355423-02-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 4,4-Dimethoxy-2-methyl-3-oxo-butyric acid (1S,2S,3R,4S)-4,7,7-trimethyl-3-naphthalen-2-yl-bicyclo[2.2.1]hept-2-yl ester
• CAS: 355423-02-8
• 化学式: C₂₇H₃₄O₅
• 分子量: 438.564
• InChiKey: RGWKSJOIUWHMRO-PNCJXRBGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.12
• 重原子数：
  32.0
• 可旋转键数：
  7.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.56
• 拓扑面积：
  61.83
• 氢给体数：
  0.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  4,4-Dimethoxy-2-methyl-3-oxo-butyric acid (1S,2S,3R,4S)-4,7,7-trimethyl-3-naphthalen-2-yl-bicyclo[2.2.1]hept-2-yl ester 在 silica gel 、 potassium carbonate 、 copper(II) sulfate 作用下， 以 甲醇 、 甲苯 为溶剂， 反应 22.0h， 生成 (S)-2-Formyl-1,3-dimethyl-4-oxo-cyclohex-2-enecarboxylic acid (1S,2S,3R,4S)-4,7,7-trimethyl-3-naphthalen-2-yl-bicyclo[2.2.1]hept-2-yl ester
  参考文献：
  名称：

  Enantioselective syntheses and resolution of the key white intermediate for the synthesis of trisporic acids

  摘要：

  Two asymmetric syntheses of the alkylated cyclohexenone carboxylic acid moiety, the key White intermediate (4a), of trisporic acids A, B and C are described. The syntheses feature a Michael addition in tandem with an aldol condensation as the central step. The resolution of this readily available intermediate is also described. Copyright (C) 1996 Elsevier Science

  DOI：

  10.1016/0957-4166(96)00109-7
• 作为产物：
  描述：

  (1S,3R,4S)-4,7,7-Trimethyl-3-naphthalen-2-yl-bicyclo[2.2.1]heptan-2-one 在 4-二甲氨基吡啶 、 lithium aluminium tetrahydride 、 4 A molecular sieve 、 thallium (I) ethoxide 作用下， 以 甲苯 为溶剂， 反应 10.5h， 生成 4,4-Dimethoxy-2-methyl-3-oxo-butyric acid (1S,2S,3R,4S)-4,7,7-trimethyl-3-naphthalen-2-yl-bicyclo[2.2.1]hept-2-yl ester
  参考文献：
  名称：

  Enantioselective syntheses and resolution of the key white intermediate for the synthesis of trisporic acids

  摘要：

  Two asymmetric syntheses of the alkylated cyclohexenone carboxylic acid moiety, the key White intermediate (4a), of trisporic acids A, B and C are described. The syntheses feature a Michael addition in tandem with an aldol condensation as the central step. The resolution of this readily available intermediate is also described. Copyright (C) 1996 Elsevier Science

  DOI：

  10.1016/0957-4166(96)00109-7