2,3,5,6-tetrahexyloxy-1,4-benzoquinone | 175229-08-0

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2,3,5,6-tetrahexyloxy-1,4-benzoquinone
• 英文别名: Tetrahexyloxy-1,4-benzoquinone；2,3,5,6-Tetrahexoxycyclohexa-2,5-diene-1,4-dione
• CAS: 175229-08-0
• 化学式: C₃₀H₅₂O₆
• 分子量: 508.739
• InChiKey: XENKKBIVEBCTLX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  10.1
• 重原子数：
  36
• 可旋转键数：
  24
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.8
• 拓扑面积：
  71.1
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  2,3,5,6-tetrahexyloxy-1,4-benzoquinone 在 氢氧化钾 、 adogen 464 作用下， 以 正庚烷 为溶剂， 反应 2.0h， 以42%的产率得到2,5-Dihexyloxy-3,6-dihydroxy-1,4-benzoquinone
  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
• 作为产物：
  描述：

  2,5-二羟基-1,4-苯喹酮 在 platinum(IV) oxide 正丁基锂 、 硼酸三甲酯 、 氢气 、 双氧水 、 溴 、 甲基三辛基氯化铵 、 potassium carbonate 、 溶剂黄146 作用下， 以 溶剂黄146 、 N,N-二甲基甲酰胺 为溶剂， 25.0~50.0 ℃ 、101.33 kPa 条件下， 反应 116.25h， 生成 2,3,5,6-tetrahexyloxy-1,4-benzoquinone
  参考文献：
  名称：

  Keegstra, Erik M. D.; Huisman, Bart-Hendrik; Paardekooper, Elizabeth M., Journal of the Chemical Society. Perkin Transactions 2 (2001), 1996, vol. 2, p. 229 - 240

  摘要：

  DOI：

文献信息

• 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.
• Keegstra, Erik M. D.; Huisman, Bart-Hendrik; Paardekooper, Elizabeth M., Journal of the Chemical Society. Perkin Transactions 2 (2001), 1996, vol. 2, p. 229 - 240
  作者：Keegstra, Erik M. D.、Huisman, Bart-Hendrik、Paardekooper, Elizabeth M.、Hoogesteger, Frans J.、Zwikker, Jan W.、Jenneskens, Leonardus W.、Kooijman, Huub、Schouten, Arie、Veldman, Nora、Spek, Anthony L.

  DOI：——

  日期：——