(1R,2R)-1,2-O-cyclohexylidene-5-methyl-3-oxo-4-cyclohexene-1,2-diol | 200204-42-8

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (1R,2R)-1,2-O-cyclohexylidene-5-methyl-3-oxo-4-cyclohexene-1,2-diol
• 英文别名: (3aR,7aR)-6-methylspiro[7,7a-dihydro-3aH-1,3-benzodioxole-2,1'-cyclohexane]-4-one
• CAS: 200204-42-8
• 化学式: C₁₃H₁₈O₃
• 分子量: 222.284
• InChiKey: ORRTXBMWGBCXKU-NEPJUHHUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  16
• 可旋转键数：
  0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.77
• 拓扑面积：
  35.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (1R,2R)-1,2-O-cyclohexylidene-5-methyl-3-oxo-4-cyclohexene-1,2-diol 在 盐酸 、 4-二甲氨基吡啶 、 sodium tetrahydroborate 、 potassium permanganate 、 cerium(III) chloride 、 10% palladium on activated carbon 、 氢气 、 magnesium sulfate 、 N,N-二异丙基乙胺 作用下， 以 甲醇 、 乙醇 、 水 为溶剂， 反应 10.0h， 生成 (3S,4R,5R,7S)-7-methylazepane-3,4,5-triol
  参考文献：
  名称：

  Synthesis of polyhydroxy 7- and N-alkyl-azepanes as potent glycosidase inhibitors

  摘要：

  An effective synthetic method for polyhydroxylated azepanes that contain an alkyl group (Me or Bu) at either the 7- or N-positions is developed. The synthetic routes are accomplished in eight to ten steps from D-(-)-quinic acid. Among the compounds synthesized, the polyhydroxy 7-butyl azepane (compound 3), which possessed the R-configuration at C-7 position, is shown to give potent inhibition against beta-galactosidase (IC50 = 3 mu M). Preliminary biological data indicate that the length of alkyl groups along with the proper stereochemistry at the C-7 position is essential for acquiring extra binding affinity. Using similar synthetic routes, the polyhydroxy N-methyl and N-butyl azepanes are synthesized for the comparison of their biological activities. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.carres.2010.11.014
• 作为产物：
  描述：

  (1R,2S,3R,5R)-1,2-O-cyclohexylidene-5-C-(hydroxymethyl)-1,2,3,5-cyclohexanetetrol 在 sodium periodate 、 重铬酸吡啶 、 molecular sieve 、 phosphate buffer 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 21.5h， 生成 (1R,2R)-1,2-O-cyclohexylidene-5-methyl-3-oxo-4-cyclohexene-1,2-diol
  参考文献：
  名称：

  Synthesis of a Key Intermediate for the Synthesis of (+)-Grandisol Utilizing (-)-Quinic Acid.

  摘要：

  以(-)-奎宁酸为手性源，合成了合成(+)-格兰迪索尔的关键中间体--(4aR, 6aR)-4a-甲基-2-氧杂双环[4.2.0]辛烷-1-酮。

  DOI：

  10.1248/cpb.45.1734

文献信息

• Synthesis of a Key Intermediate for the Synthesis of (+)-Grandisol Utilizing (-)-Quinic Acid.
  作者：Keizo MATSUO、Masakatsu MORITA、Ken-ichi KAWASHIMA

  DOI：10.1248/cpb.45.1734

  日期：——

  A key intermediate for the synthesis of (+)-grandisol, (4aR, 6aR)-4a-methyl-2-oxabicyclo[4.2.0]octan-1-one, was synthesized starting from (-)-quinic acid as the chiral source.

  以(-)-奎宁酸为手性源，合成了合成(+)-格兰迪索尔的关键中间体--(4aR, 6aR)-4a-甲基-2-氧杂双环[4.2.0]辛烷-1-酮。
• Synthesis of polyhydroxy 7- and N-alkyl-azepanes as potent glycosidase inhibitors
  作者：Tzenge-Lien Shih、Ming-Tsung Liang、Kuen-Da Wu、Chun-Hung Lin

  DOI：10.1016/j.carres.2010.11.014

  日期：2011.2

  An effective synthetic method for polyhydroxylated azepanes that contain an alkyl group (Me or Bu) at either the 7- or N-positions is developed. The synthetic routes are accomplished in eight to ten steps from D-(-)-quinic acid. Among the compounds synthesized, the polyhydroxy 7-butyl azepane (compound 3), which possessed the R-configuration at C-7 position, is shown to give potent inhibition against beta-galactosidase (IC50 = 3 mu M). Preliminary biological data indicate that the length of alkyl groups along with the proper stereochemistry at the C-7 position is essential for acquiring extra binding affinity. Using similar synthetic routes, the polyhydroxy N-methyl and N-butyl azepanes are synthesized for the comparison of their biological activities. (C) 2010 Elsevier Ltd. All rights reserved.