1,4/2-cyclohexanetriol | 13466-89-2

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 1,4/2-cyclohexanetriol
• 英文别名: (+/-)-(1R,2R,4S)-cyclohexane-1,2,4-triol；(+/-)-cyclohexanetriol-(1r.2t.4c)；(+/-)-Cyclohexantriol-(1r.2t.4c)；rel-(1R,2R,4S)-1,2,4-Cyclohexanetriol；(1R,2R,4S)-cyclohexane-1,2,4-triol
• CAS: 13466-89-2
• 化学式: C₆H₁₂O₃
• 分子量: 132.159
• InChiKey: ZHMPXIDAUXCKIQ-KVQBGUIXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.8
• 重原子数：
  9
• 可旋转键数：
  0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  60.7
• 氢给体数：
  3
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  1,4/2-cyclohexanetriol 在 platinum(IV) oxide 吡啶 、 4-二甲氨基吡啶 、 氢气 作用下， 以 乙醇 、 水 为溶剂， 20.0~30.0 ℃ 、310.27 kPa 条件下， 反应 24.0h， 生成 (+/-)-(1R,2R,4S)-cyclohexane-1,2,4-triol trisphosphate
  参考文献：
  名称：

  Small Molecule Analogs of Phospholipid-Metal Ion Binding Sites: Synthesis and Molecular Modeling of Cyclohexane-1,2,4-triol Trisphosphates

  摘要：

  Four diastereomeric cyclohexane-1,2,4-triol trisphosphates were synthesized to serve as small molecule analogs of putative phospholipid-metal ion binding sites. The parent cyclehexane-1,2,4-triols were prepared and phosphorylated. Deprotection of the tris(diphenylphosphates) provided four regiochemical isomers: two with the trans-1,2-phosphate moiety, (+/-)-(1R,2R,4S)- and (+/-)-(1R,2R,4R)-cyclohexane-1,2,4-triol tris(ammonium hydrogen phosphate), and two with the cis-1,2-phosphate moiety, (+/-)-(1R,2S,4R)- and (+/-)-(1R,2S, 4S)-cyclohexane-1,2,4-triol tris(ammonium hydrogen phosphate). Molecular mechanics calculations for each trisphosphate and the Ca(II) and Mg(II) complex were performed using MacroModel. Results from the molecular modeling studies indicate that two of the criteria for the suitability of the trisphosphates as analogs of phospholipid-metal ion binding sites are satisfied: (1) anionic groups which can interactively bind a metal ion and (2) interphosphate distances comparable to the phosphate-phosphate distances of a computational phospholipid surface. (C) 1994 Academic Press, Inc.

  DOI：

  10.1006/bioo.1994.1014
• 作为产物：
  描述：

  3-cyclohexen-1-ol 在 过氧化氢苯甲酰 作用下， 生成 1,4/2-cyclohexanetriol
  参考文献：
  名称：

  Alicyclic Carbohydrates. XXX.^1a Synthesis of the Remaining Cyclohexanetriols. Nuclear Magnetic Resonance Studies on the Nine Isomers^1b

  摘要：

  DOI：

  10.1021/jo01348a003

文献信息

• The preparation of cyclohexanepentols from inositols by deoxygenation
  作者：Stephen J. Angyal、Léon Odier

  DOI：10.1016/s0008-6215(00)81001-0

  日期：1982.3

  inositols by blocking all but one hydroxyl group, converting the free hydroxyl group into its S -methyl dithiocarbonate, and treating it with tributylstannane. Suitable blocking-groups are methyl, benzyl, and methylthiomethyl ethers, and acetals. One cyclohexanepentol was prepared by the reductive deamination of an aminodeoxyinositol.

  摘要从肌醇中合成了几种环己烷戊醇，方法是封闭除一个羟基外的所有羟基，将游离羟基转化为S-甲基二硫代碳酸酯，并用三丁基锡烷处理。合适的保护基是甲基，苄基和甲硫基甲基醚和乙缩醛。一种环己烷戊醇是通过氨基脱氧肌醇的还原性脱氨基反应制得的。
• Small Molecule Analogs of Phospholipid-Metal Ion Binding Sites: Synthesis and Molecular Modeling of Cyclohexane-1,2,4-triol Trisphosphates
  作者：J.C. Amburgey、S.W. Shuey、L.G. Pedersen、R.G. Hiskey

  DOI：10.1006/bioo.1994.1014

  日期：1994.6

  Four diastereomeric cyclohexane-1,2,4-triol trisphosphates were synthesized to serve as small molecule analogs of putative phospholipid-metal ion binding sites. The parent cyclehexane-1,2,4-triols were prepared and phosphorylated. Deprotection of the tris(diphenylphosphates) provided four regiochemical isomers: two with the trans-1,2-phosphate moiety, (+/-)-(1R,2R,4S)- and (+/-)-(1R,2R,4R)-cyclohexane-1,2,4-triol tris(ammonium hydrogen phosphate), and two with the cis-1,2-phosphate moiety, (+/-)-(1R,2S,4R)- and (+/-)-(1R,2S, 4S)-cyclohexane-1,2,4-triol tris(ammonium hydrogen phosphate). Molecular mechanics calculations for each trisphosphate and the Ca(II) and Mg(II) complex were performed using MacroModel. Results from the molecular modeling studies indicate that two of the criteria for the suitability of the trisphosphates as analogs of phospholipid-metal ion binding sites are satisfied: (1) anionic groups which can interactively bind a metal ion and (2) interphosphate distances comparable to the phosphate-phosphate distances of a computational phospholipid surface. (C) 1994 Academic Press, Inc.
• Alicyclic Carbohydrates. XXX.^1a Synthesis of the Remaining Cyclohexanetriols. Nuclear Magnetic Resonance Studies on the Nine Isomers^1b
  作者：G. E. McCasland、M. O. Naumann、Lois J. Durham

  DOI：10.1021/jo01348a003

  日期：1966.10