methyl 3α,4α-isopropylidenedioxy-5β-formylcyclohex-1-ene-1-carboxylate | 145214-96-6

• 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-formylcyclohex-1-ene-1-carboxylate
• CAS: 145214-96-6
• 化学式: C₁₂H₁₆O₅
• 分子量: 240.256
• InChiKey: SBSMCLAJOBAFEG-KXUCPTDWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.82
• 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：
  0.67
• 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：

  methyl 3α,4α-isopropylidenedioxy-5β-formylcyclohex-1-ene-1-carboxylate 在 溶剂黄146 、 三氟化硫吗啉 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 120.0h， 生成 methyl 3α,4α-dihydroxy-5β-(difluoromethyl)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-isopropylidenedioxy-5β-(acetoxymethyl)cyclohex-1-ene-1-carboxylate 在 ammonium hydroxide 、 pyridinium chlorochromate 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 52.0h， 生成 methyl 3α,4α-isopropylidenedioxy-5β-formylcyclohex-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

文献信息

• Synthesis of 5-homoshikimic acid and some fluorinated derivatives as potential inhibitors of 5-enolpyruvylshikimate-3-phosphate synthase
  作者：Malcolm M. Campbell、Mary F. Mahon、Malcolm Sainsbury、Philip A. Searle、Gareth M. Davies

  DOI：10.1016/s0040-4020(01)89449-7

  日期：——

  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