potassium 3-dehydroquinate | 494211-79-9

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: potassium 3-dehydroquinate
• 英文别名: Potassium (1R,3R,4S)-1,3,4-trihydroxy-5-oxocyclohexane-1-carboxylate；potassium;(1R,3R,4S)-1,3,4-trihydroxy-5-oxocyclohexane-1-carboxylate
• CAS: 494211-79-9
• 化学式: C₇H₉O₆*K
• 分子量: 228.243
• InChiKey: XOXNBNMEMILWBJ-HOMRGJANSA-M

计算性质

• 辛醇/水分配系数(LogP)：
  -6.44
• 重原子数：
  14
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.71
• 拓扑面积：
  118
• 氢给体数：
  3
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  potassium 3-dehydroquinate 在 Amberlite IR-120 作用下， 以 水 为溶剂， 反应 0.08h， 以140 mg的产率得到1,3beta,4alpha-三羟基-5-氧代环己烷-1beta-羧酸
  参考文献：
  名称：

  A Convenient Method for the Synthesis of Dehydroquinic Acid

  摘要：

  A convenient synthesis of dehydroquinic acid and its corresponding methyl ester are described. Protection of the trans diol of quinic acid, followed by PCC oxidation gave fully protected dehydroquinic acid. This gave methyl dehydroquinate on mild, acid catalyzed hydrolysis. Ester hydrolysis then gave potassium dehydroquinate which was treated with amberlite to afford dehydroquinic acid.

  DOI：

  10.1081/scc-120015805
• 作为产物：
  描述：

  (2S,3S,4aR,6S,8R,8aR)-八氢-6,8-二羟基-2,3-二甲氧基-2,3-二甲基-1,4-苯并二氧杂环己-6-羧酸甲酯 在 氢氧化钾 、 4 A molecular sieve 、 pyridinium chlorochromate 、 三氟乙酸 作用下， 以 二氯甲烷 、 水 为溶剂， 反应 15.42h， 生成 potassium 3-dehydroquinate
  参考文献：
  名称：

  A Convenient Method for the Synthesis of Dehydroquinic Acid

  摘要：

  A convenient synthesis of dehydroquinic acid and its corresponding methyl ester are described. Protection of the trans diol of quinic acid, followed by PCC oxidation gave fully protected dehydroquinic acid. This gave methyl dehydroquinate on mild, acid catalyzed hydrolysis. Ester hydrolysis then gave potassium dehydroquinate which was treated with amberlite to afford dehydroquinic acid.

  DOI：

  10.1081/scc-120015805

文献信息

• A simple method for the preparation of 3-hydroxyiminodehydroquinate,The IUPAC name for 3-hydroxyiminodehydroquinate is (1S,4R,5R)-1,4,5-trihydroxy-3-(hydroxyimino)cyclohexane-1-carboxylate. a potent inhibitor of type II dehydroquinase
  作者：Christine Le Sann、Chris Abell、Andrew D. Abell

  DOI：10.1039/b206066c

  日期：2002.9.11

  A number of routes to 3-hydroxyiminodehydroquinate 4, one of the most potent inhibitors of type II dehydroquinase that is currently known, have been investigated. Methods based on the existing literature synthesis, i.e. oxime formation of a suitably C-4 and C-5 protected methyl 3-dehydroquinate derivative were initially studied. Benzoyl protection as in 11 did give the desired product but in low overall yield. An alternative BBA protection strategy starting with 7 was successful in generating a C-4/C-5 analogue of the desired oxime 4 in high yield. Further investigation revealed that it was unnecessary to protect the dehydroquinate precursor, hence the potassium salt corresponding to oxime 4 was simply synthesised as a single isomer from methyl dehydroquinate 10.

  3-hydroxyiminodehydroquinate 4 是目前已知的最有效的 II 型脱氢喹啉酶抑制剂之一。最初研究的是基于现有文献合成的方法，即通过肟形成适当的 C-4 和 C-5 保护的 3-脱氢喹啉酸甲酯衍生物。如 11 所述的苯甲酰基保护确实能得到所需的产物，但总收率较低。从 7 开始的另一种 BBA 保护策略成功地以高产率生成了所需肟 4 的 C-4/C-5 类似物。进一步的研究表明，没有必要对脱氢葵酸酯前体进行保护，因此只需从脱氢葵酸甲酯 10 中合成与肟 4 相对应的单异构体钾盐即可。