(1S,2S,4R,5S)-4-Allyloxy-5-hydroxy-cyclohexane-1,2-dicarboxylic acid dimethyl ester | 371974-84-4

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (1S,2S,4R,5S)-4-Allyloxy-5-hydroxy-cyclohexane-1,2-dicarboxylic acid dimethyl ester
• 英文别名: dimethyl (1S,2S,4S,5R)-4-hydroxy-5-prop-2-enoxycyclohexane-1,2-dicarboxylate
• CAS: 371974-84-4
• 化学式: C₁₃H₂₀O₆
• 分子量: 272.298
• InChiKey: BJWJBYWDRSYMCS-XWLWVQCSSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.4
• 重原子数：
  19
• 可旋转键数：
  7
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.69
• 拓扑面积：
  82.1
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  (1S,2S,4R,5S)-4-Allyloxy-5-hydroxy-cyclohexane-1,2-dicarboxylic acid dimethyl ester 在 lithium hydroxide 作用下， 以 甲醇 为溶剂， 生成 (1S,2S,4S,5R)-2-Carbamoyl-4,5-bis-phenylcarbamoyloxy-cyclohexanecarboxylic acid methyl ester
  参考文献：
  名称：

  Solid-phase synthesis of combinatorial libraries based on enatiomerically pure (1S,2S,4R,5S)-4,5-dihydroxycyclohexan-1,2-dicarboxylic acid scaffolds

  摘要：

  The conditions for solid-phase functionalization of the new enantio-pure scaffold 1 to give libraries of general formula 4 have been derived. (C) 2002 Editions scientifiques et medicales Elsevier SAS. All rights reserved.

  DOI：

  10.1016/s0014-827x(02)01306-x
• 作为产物：
  描述：

  rac-trans-4,5-bis(methoxycarbonyl)cyclohexene 在 osmium (III) chloride 、 N,N-二乙基乙胺氧化物 、 水 、 二正丁基氧化锡 作用下， 以 二氯甲烷 、 苯 为溶剂， 反应 69.0h， 生成 (1S,2S,4R,5S)-4-Allyloxy-5-hydroxy-cyclohexane-1,2-dicarboxylic acid dimethyl ester
  参考文献：
  名称：

  Stereoselective Synthesis of Conformationally Constrained Cyclohexanediols:  A Set of Molecular Scaffolds for the Synthesis of Glycomimetics

  摘要：

  The practical, stereoselective synthesis of the three diastereoisomeric 1,2-trans-dicarboxy-4,5-cyclohexanediols. 1-3 (DCCHDs) is described, starting from a common precursor, easily available in both enantiomeric forms. The regioselective derivatization of all functional groups of I is also reported. The three DCCHDs are locked in a single chair conformation and thus can be used to mimic vicinally disubstituted monosaccharides of any relative configuration.

  DOI：

  10.1021/jo015570b