1,2:5,6-Di-O-cyclohexylidene-(-)-inositol | 54712-58-2

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 1,2:5,6-Di-O-cyclohexylidene-(-)-inositol
• 英文别名: (-)-1,2:5,6-Di-O-cyclohexylidene-L-inositol
• CAS: 54712-58-2
• 化学式: C₁₈H₂₈O₆
• 分子量: 340.417
• InChiKey: PHAPESVEHHOBEI-KPRKPIBOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  24
• 可旋转键数：
  0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  77.4
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  1,2:5,6-Di-O-cyclohexylidene-(-)-inositol 在 sodium hydride 、 溶剂黄146 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 4.5h， 生成 3,4-Di-O-hexyl-(-)-inositol
  参考文献：
  名称：

  News on Inositol Liquid Crystals¹

  摘要：

  A greater number of selected, partially O-alkylated derivatives of three (myo-, scyllo-, and chiro-) inositols, stereoisomers of 1,2,3,4,5,6-hexahydroxycyclohexane, as well as of hexahydroxybenzene and tetrahydroxy-1,4-benzoquinone were synthesized and characterized by usual methods. From the study of the various liquid crystalline target compounds (long-chained alkyl ethers) by polarizing microscopy and differential scanning calorimetry it emerges that the occurrence, type, and stability of their mesophases are clearly determined by the number, the position, and the stereochemical arrangement of both the hydroxyl groups and the alkoxy chains on the cyclohexane ring which is discussed in detail. Here, unsaturated six-membered ring units-for example quinoic or aromatic in character-as carriers of the numerous hydroxyl functions have been proved damaging to the exhibition of mesophases; our multihydroxy model compounds of this type have not been found liquid crystalline. In general, it was found that axial hydroxy and alkoxy groups destabilize the smectic A or hexagonal columnar phase exhibited here. Moreover two types of mesophase transformation from hexagonal columnar to smectic A have been found, i) by changing the stereochemistry of two vicinal hydroxyl functions in a peg-shaped chiro-inositol diether (derived from quebrachitol) or ii) by blocking of a (special) equatorial hydroxyl function in a peg-shaped myo-inositol diether through etherification. A complete homologous stereoisomeric series (five members) of myo- and scyllo-inositol monoalkyl ethers with each a dodecyl chain at their respective oxygen functions is also presented; the three thermomesogenic ones of them exhibit the smectic A phase. In this connection and with regard to a homologous series of D-glucopyranose monoethers, molecular symmetry effects originating from the different localization of the one ether group in both homologous series on their ability/inability of mesophase formation are discussed in detail.

  DOI：

  10.1080/10587259408037774

文献信息

• Monoesterification of di-O-isopropylidene and di-O-cyclohexylidene chiro-inositols
  作者：Ghislaine Cousins、Andrew Falshaw、John O. Hoberg

  DOI：10.1016/s0008-6215(03)00072-7

  日期：2003.4

  Monoesterification Of D- or L-chiro-inositols protected as diacetals proceeds in excellent selectivity and yields. The metal-catalyzed, one-step reaction proceeds at room temperature under an air atmosphere and has been developed using a range of examples. (C) 2003 Elsevier Science Ltd. All rights reserved.
• News on Inositol Liquid Crystals¹
  作者：Klaus Praefcke、Dirk Blunk、Joachim Hempel

  DOI：10.1080/10587259408037774

  日期：1994.3

  A greater number of selected, partially O-alkylated derivatives of three (myo-, scyllo-, and chiro-) inositols, stereoisomers of 1,2,3,4,5,6-hexahydroxycyclohexane, as well as of hexahydroxybenzene and tetrahydroxy-1,4-benzoquinone were synthesized and characterized by usual methods. From the study of the various liquid crystalline target compounds (long-chained alkyl ethers) by polarizing microscopy and differential scanning calorimetry it emerges that the occurrence, type, and stability of their mesophases are clearly determined by the number, the position, and the stereochemical arrangement of both the hydroxyl groups and the alkoxy chains on the cyclohexane ring which is discussed in detail. Here, unsaturated six-membered ring units-for example quinoic or aromatic in character-as carriers of the numerous hydroxyl functions have been proved damaging to the exhibition of mesophases; our multihydroxy model compounds of this type have not been found liquid crystalline. In general, it was found that axial hydroxy and alkoxy groups destabilize the smectic A or hexagonal columnar phase exhibited here. Moreover two types of mesophase transformation from hexagonal columnar to smectic A have been found, i) by changing the stereochemistry of two vicinal hydroxyl functions in a peg-shaped chiro-inositol diether (derived from quebrachitol) or ii) by blocking of a (special) equatorial hydroxyl function in a peg-shaped myo-inositol diether through etherification. A complete homologous stereoisomeric series (five members) of myo- and scyllo-inositol monoalkyl ethers with each a dodecyl chain at their respective oxygen functions is also presented; the three thermomesogenic ones of them exhibit the smectic A phase. In this connection and with regard to a homologous series of D-glucopyranose monoethers, molecular symmetry effects originating from the different localization of the one ether group in both homologous series on their ability/inability of mesophase formation are discussed in detail.