methyl 3α,4α-dihydroxy-5β-cyclohex-1-ene-1-carboxylate | 134039-36-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: methyl 3α,4α-dihydroxy-5β-cyclohex-1-ene-1-carboxylate
• 英文别名: methyl 3α,4α-dihydroxy-5β-(N,N-di(p-nitrobenzenesulphonyl)aminomethyl)cyclohex-1-ene-1-carboxylate；methyl (3R,4S,5S)-5-[[bis[(4-nitrophenyl)sulfonyl]amino]methyl]-3,4-dihydroxycyclohexene-1-carboxylate
• CAS: 134039-36-4；134107-76-9
• 化学式: C₂₁H₂₁N₃O₁₂S₂
• 分子量: 571.543
• InChiKey: OHUPMEPUDRGHHR-KPOBHBOGSA-N

物化性质

• 沸点：
  780.2±70.0 °C(Predicted)
• 密度：
  1.616±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.1
• 重原子数：
  38
• 可旋转键数：
  8
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  247
• 氢给体数：
  2
• 氢受体数：
  13

反应信息

• 作为反应物：
  描述：

  methyl 3α,4α-dihydroxy-5β-cyclohex-1-ene-1-carboxylate 在 potassium iodide 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 生成 methyl 3α,4α-isopropylidenedioxy-5β-(acetoxymethyl)cyclohex-1-ene-1-carboxylate
  参考文献：
  名称：

  Synthesis of (±)-homogabaculine and (±)-homoshikimic acid

  摘要：

  Syntheses of homogabaculine and homoshikimic acid are described utilising the base mediated ring opening of the cycloadducts of methyl acrylate and N-carbamoyl-1,2-dihydropyridines.

  DOI：

  10.1016/s0040-4039(00)92128-2
• 作为产物：
  描述：

  methyl 5-cyclohexa-1,3-diene-1-carboxylate 在 ammonium hydroxide 作用下， 生成 methyl 3α,4α-dihydroxy-5β-cyclohex-1-ene-1-carboxylate
  参考文献：
  名称：

  Synthesis of (±)-homogabaculine and (±)-homoshikimic acid

  摘要：

  Syntheses of homogabaculine and homoshikimic acid are described utilising the base mediated ring opening of the cycloadducts of methyl acrylate and N-carbamoyl-1,2-dihydropyridines.

  DOI：

  10.1016/s0040-4039(00)92128-2

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
• Synthesis of (±)-homogabaculine and (±)-homoshikimic acid
  作者：Malcolm M. Campbell、Mary F. Mahon、Malcolm Sainsbury、Philip A. Searle、Gareth M. Davies

  DOI：10.1016/s0040-4039(00)92128-2

  日期：1991.2

  Syntheses of homogabaculine and homoshikimic acid are described utilising the base mediated ring opening of the cycloadducts of methyl acrylate and N-carbamoyl-1,2-dihydropyridines.