1,2,3,4,6-Penta(O-benzyl)-myo-inositol | 30694-52-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 1,2,3,4,6-Penta(O-benzyl)-myo-inositol
• 英文别名: 1,2,3,4,6-Penta-O-benzyl-myo-inositol
• CAS: 30694-52-1
• 化学式: C₄₁H₄₂O₆
• 分子量: 630.781
• InChiKey: PLKAJAVHVAUNLR-LNQZRZQPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.29
• 重原子数：
  47.0
• 可旋转键数：
  15.0
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  66.38
• 氢给体数：
  1.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  1,2,3,4,6-Penta(O-benzyl)-myo-inositol 在 2-碘酰基苯甲酸 作用下， 以 乙酸乙酯 为溶剂， 反应 6.0h， 以96%的产率得到1,2,3,4,6-penta-O-benzyl-myo-inosose
  参考文献：
  名称：

  肌醇到芳烃–无苯合成多氧化芳烃

  摘要：

  描述了一种由肌醇制备苯衍生物的方法，肌醇是一种可大量利用的植物化学物质。肌苷的1,3-桥缩乙缩醛经过分步消除，导致形成多氧化苯衍生物。该芳构化反应通过可被分离的β-烷氧基烯酮的中间体进行。从肌醇开始的该反应顺序为制备包括多氧合联苯的多氧合苯衍生物提供了新的途径。该合成方案证明了肌醇作为芳香族化合物可持续的非石油化学资源的潜力。

  DOI：

  10.1016/j.carres.2018.03.007
• 作为产物：
  描述：

  (1R,5S,6R,7s,8S,9s)-7-(allyloxy)-6,8,9-tris(benzyloxy)-2,4-dioxabicyclo[3.3.1]nonane 在 盐酸 、 sodium hydride 、 potassium carbonate 、 三苯基膦钯 作用下， 以 甲醇 、 乙醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 62.0h， 生成 1,2,3,4,6-Penta(O-benzyl)-myo-inositol
  参考文献：
  名称：

  肌醇到芳烃–无苯合成多氧化芳烃

  摘要：

  描述了一种由肌醇制备苯衍生物的方法，肌醇是一种可大量利用的植物化学物质。肌苷的1,3-桥缩乙缩醛经过分步消除，导致形成多氧化苯衍生物。该芳构化反应通过可被分离的β-烷氧基烯酮的中间体进行。从肌醇开始的该反应顺序为制备包括多氧合联苯的多氧合苯衍生物提供了新的途径。该合成方案证明了肌醇作为芳香族化合物可持续的非石油化学资源的潜力。

  DOI：

  10.1016/j.carres.2018.03.007

文献信息

• Synthesis of racemic myo-inositol 1,4,5-trismethylphosphonate, myo-inositol 4,5-bismethylphosphonate and myo-inositol 5-methylphosphonate via a phosphinate approach
  作者：Henrica A.M. Willems、Gerrit H. Veeneman、Pieter Westerduin

  DOI：10.1016/0040-4039(92)88146-v

  日期：1992.4

  Synthesis of the (rac.) myo-inositol phosphate isosteric analogues 1,4,5-trismethylphosphonate, 4,5-bismethylphosphonate, and 5-methylphosphonate was accomplished using a phosphinate approach.

  （外消旋）肌醇磷酸酯等排类似物1,4,5-三三甲基膦酸酯，4,5-双甲基膦酸酯和5-甲基膦酸酯的合成是使用次膦酸酯方法完成的。
• Relative reactivity of hydroxyl groups in inositol derivatives: role of metal ion chelation
  作者：Subramanian Devaraj、Rajendra C. Jagdhane、Mysore S. Shashidhar

  DOI：10.1016/j.carres.2009.04.007

  日期：2009.7

  one hydroxyl group via their alkali metal alkoxides (sodium or lithium) preferentially occurs at a hydroxyl group having a vicinal cis-oxygen atom. In general the observed selectivity is relatively higher for lithium alkoxides than for the corresponding sodium alkoxide. The observed regioselectivity is also dependent on other factors such as the solvent and reaction temperature. A perusal of the results

  含有一个以上羟基的肌醇衍生物经由其碱金属醇盐（钠或锂）的O-烷基化优先发生在具有邻位顺式氧原子的羟基上。通常，观察到的对于烷氧基锂的选择性比对相应的烷氧基钠的选择性更高。观察到的区域选择性还取决于其他因素，例如溶剂和反应温度。对本文提供的结果以及文献中提供的结果的仔细研究表明，肌醇衍生物对金属离子的螯合在观察到的区域选择性中起着重要作用。与反应的羟基的轴向或赤道位置有关的立体因素对这些O-烷基化反应的结果没有太大贡献。
• Offer, John L.; Voorheis, H. Paul; Metcalfe, James C., Journal of the Chemical Society. Perkin transactions I, 1992, # 8, p. 953 - 960
  作者：Offer, John L.、Voorheis, H. Paul、Metcalfe, James C.、Smith, Gerry A.

  DOI：——

  日期：——
• 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.