3α,4α-dihydroxy-5β-(fluoromethyl)cyclohex-1-ene-1-carboxylic acid | 145214-83-1

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 3α,4α-dihydroxy-5β-(fluoromethyl)cyclohex-1-ene-1-carboxylic acid
• 英文别名: (3R,4S,5R)-5-(fluoromethyl)-3,4-dihydroxycyclohexene-1-carboxylic acid
• CAS: 145214-83-1
• 化学式: C₈H₁₁FO₄
• 分子量: 190.171
• InChiKey: TYAUHOZVHSJGEO-XVMARJQXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.5
• 重原子数：
  13
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.62
• 拓扑面积：
  77.8
• 氢给体数：
  3
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  methyl 3α,4α-isopropylidenedioxy-5β-(acetoxymethyl)cyclohex-1-ene-1-carboxylate 在 ammonium hydroxide 、 sodium hydroxide 、 溶剂黄146 、 三氟化硫吗啉 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 、 水 为溶剂， 反应 99.5h， 生成 3α,4α-dihydroxy-5β-(fluoromethyl)cyclohex-1-ene-1-carboxylic acid
  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