1,2,4-三羟基环己烷

• 分子结构分类: 有机化合物 - 有机氧化合物
• 中文名称: 1,2,4-三羟基环己烷
• 英文名称: (+/-)-(1R,2R,4R)-cyclohexane-1,2,4-triol
• 英文别名: (+/-)-cyclohexanetriol-(1r.2t.4t)；(+/-)-Cyclohexantriol-(1r.2t.4t)；(1R,2R,4R)-cyclohexane-1,2,4-triol
• 化学式: C₆H₁₂O₃
• 分子量: 132.159
• InChiKey: ZHMPXIDAUXCKIQ-HSUXUTPPSA-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：

  1,2,4-三羟基环己烷 在 四氮唑 、 间氯过氧苯甲酸 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 3.0h， 生成 rac-3,3',3''-(((1R,2R,4R)-cyclohexane-1,2,4-triyl)tris(oxy))tris(1,5-dihydrobenzo[e][1,3,2]dioxaphosphepine 3-oxide)
  参考文献：
  名称：

  Synthesis of (±) Cyclohexane-1 (R),2 (R),4 (R)-Triol-Triphosphate, a Deoxygenated Analog of myo-Inositol -1,4,5- Triphosphate

  摘要：

  For the use in the studies of inositol-phosphates, (+/-) cyclohexane-1(R), 2(R), 4(R)-triol-triphosphate 2 was synthesized from anisole. The synthesis used 1,2-benzenedimethanol as a ketone and phosphate protective group which induced easy cristallization of the intermediates. Regeneration of the free ketone 9 under mild conditions followed by its selective reduction and phosphorylation by the phosphite method gave the expected compound 2.

  DOI：

  10.1016/0040-4039(92)88127-q
• 作为产物：
  描述：

  1,5-dihydro-7'-oxaspiro[benzo[e][1,3]dioxepine-3,3'-bicyclo[4.1.0]heptane] 在 palladium on activated charcoal 吡啶 、 盐酸 、 sodium tetrahydroborate 、 氢气 、 碳酸氢钠 、 溶剂黄146 作用下， 以 乙醇 、 二氯甲烷 为溶剂， 反应 53.5h， 生成 1,2,4-三羟基环己烷
  参考文献：
  名称：

  Synthesis of (±) Cyclohexane-1 (R),2 (R),4 (R)-Triol-Triphosphate, a Deoxygenated Analog of myo-Inositol -1,4,5- Triphosphate

  摘要：

  For the use in the studies of inositol-phosphates, (+/-) cyclohexane-1(R), 2(R), 4(R)-triol-triphosphate 2 was synthesized from anisole. The synthesis used 1,2-benzenedimethanol as a ketone and phosphate protective group which induced easy cristallization of the intermediates. Regeneration of the free ketone 9 under mild conditions followed by its selective reduction and phosphorylation by the phosphite method gave the expected compound 2.

  DOI：

  10.1016/0040-4039(92)88127-q

文献信息

• Synthesis of 1D-3-deoxy-, 1D-2,3-dideoxy-, and 1D-2,3,6-trideoxy-myo-inositol 1,4,5-trisphosphate from quebrachitol, their binding affinities, and calcium release activity
  作者：A. P. Kozikowski、V. I. Ognyanov、A. H. Fauq、S. R. Nahorski、R. A. Wilcox

  DOI：10.1021/ja00064a002

  日期：1993.6

  Syntheses of three optically pure, deoxygenated myo-inositol 1,4,5-trisphosphate analogues from quebrachitol are reported together with their binding affinities and 45 Ca 2+ release activity. The ligand-binding affinities of the analogues were determined using membrane preparations from bovine adrenal cortex. The 45 Ca 2+ release activities were compared to that of Ins(1,4,5)P 3 , using the calcium

  三种光学纯的、脱氧的肌醇 1,4,5-三磷酸酯类似物的合成与它们的结合亲和力和 45 Ca 2+ 释放活性一起报告。使用来自牛肾上腺皮质的膜制剂测定类似物的配体结合亲和力。45 Ca 2+ 释放活性与Ins(1,4,5)P 3 的释放活性进行了比较，使用皂苷透化的SH-SY5Y人神经母细胞瘤细胞的钙动员受体。1D-3-deoxy-Ins(1,4,5)P 3 (16) 和 1D-2,3-dideoxy-Ins(1,4,5)P 3 (11) 表现出非常有效的配体和激动剂特性，而1D-2,3,6-trideoxy-Ins(1,4,5)P 3 (19) 的效力要低得多。这些数据为 Ins(1,4,5)P 3 的 HO-6 在其结合亲和力和 Ca 2+ 动员活性中发挥的关键作用提供了确凿的证据
• 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
• TREATMENT OF AUTISTIC SPECTRUM DISORDER
  申请人：Price Richard Louis

  公开号：US20170151216A1

  公开（公告）日：2017-06-01

  A kit, optionally for treating a patient having ASD, is disclosed. The kit includes at least one first package and at least one second package. The first package contains an alpha-2 adrenergic agonist in an extended release dosage form. The second package contains inositol.
• Synthesis of (±) Cyclohexane-1 (R),2 (R),4 (R)-Triol-Triphosphate, a Deoxygenated Analog of myo-Inositol -1,4,5- Triphosphate
  作者：Laurent Schmitt、Bernard Spiess、Gilbert Schlewer

  DOI：10.1016/0040-4039(92)88127-q

  日期：1992.4

  For the use in the studies of inositol-phosphates, (+/-) cyclohexane-1(R), 2(R), 4(R)-triol-triphosphate 2 was synthesized from anisole. The synthesis used 1,2-benzenedimethanol as a ketone and phosphate protective group which induced easy cristallization of the intermediates. Regeneration of the free ketone 9 under mild conditions followed by its selective reduction and phosphorylation by the phosphite method gave the expected compound 2.