methyl 3α,4α-isopropylidenedioxy-5β-(fluoromethyl)cyclohex-1-ene-1-carboxylate | 145214-94-4

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: methyl 3α,4α-isopropylidenedioxy-5β-(fluoromethyl)cyclohex-1-ene-1-carboxylate
• CAS: 145214-94-4
• 化学式: C₁₂H₁₇FO₄
• 分子量: 244.263
• InChiKey: GOPIVJXIHZXJMK-KXUCPTDWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  17.0
• 可旋转键数：
  2.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.75
• 拓扑面积：
  44.76
• 氢给体数：
  0.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  methyl 3α,4α-isopropylidenedioxy-5β-(fluoromethyl)cyclohex-1-ene-1-carboxylate 在 溶剂黄146 作用下， 以 四氢呋喃 为溶剂， 反应 48.0h， 以97%的产率得到methyl 3α,4α-dihydroxy-5β-(fluoromethyl)cyclohex-1-ene-1-carboxylate
  参考文献：
  名称：

  Synthesis of 5-homoshikimic acid and some fluorinated derivatives as potential inhibitors of 5-enolpyruvylshikimate-3-phosphate synthase

  摘要：

  The synthesis of (+/-)-5-homoshikimic acid, its 5-fluoromethyl and difluoromethyl analogues are described from the cycloadducts of 5,6-dihydro-1-(t)butyloxycarbonylpyridine and methyl acrylate. The adducts on ring opening afford methyl 5-(t)butoxycarbonylmethyl-5,6-di-hydrobenzoate, which may be 3,4-cis-dihydroxylated and converted in a series of steps into the title compounds

  DOI：

  10.1016/s0040-4020(01)89449-7
• 作为产物：
  描述：

  methyl 3α,4α-dihydroxy-5β-(acetoxymethyl)cyclohex-1-ene-1-carboxylate 在 ammonium hydroxide 、 对甲苯磺酸 、 三氟化硫吗啉 作用下， 以 甲醇 、 二氯甲烷 、 丙酮 为溶剂， 反应 43.5h， 生成 methyl 3α,4α-isopropylidenedioxy-5β-(fluoromethyl)cyclohex-1-ene-1-carboxylate
  参考文献：
  名称：

  Synthesis of 5-homoshikimic acid and some fluorinated derivatives as potential inhibitors of 5-enolpyruvylshikimate-3-phosphate synthase

  摘要：

  The synthesis of (+/-)-5-homoshikimic acid, its 5-fluoromethyl and difluoromethyl analogues are described from the cycloadducts of 5,6-dihydro-1-(t)butyloxycarbonylpyridine and methyl acrylate. The adducts on ring opening afford methyl 5-(t)butoxycarbonylmethyl-5,6-di-hydrobenzoate, which may be 3,4-cis-dihydroxylated and converted in a series of steps into the title compounds

  DOI：

  10.1016/s0040-4020(01)89449-7