6,8,9-tris-benzyloxy-3-phenyl-2,4-dioxa-bicyclo[3.3.1]nonan-7-ol | 940000-68-0

• 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: 6,8,9-tris-benzyloxy-3-phenyl-2,4-dioxa-bicyclo[3.3.1]nonan-7-ol
• CAS: 940000-68-0
• 化学式: C₃₄H₃₄O₆
• 分子量: 538.64
• InChiKey: IPRKKZFGNXIRQZ-ZOJKQRNASA-N

物化性质

• 熔点：
  102-104 °C(Solvent: Dichloromethane; Ligroine)
• 沸点：
  686.0±55.0 °C(predicted)
• 密度：
  1.26±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.6
• 重原子数：
  40.0
• 可旋转键数：
  10.0
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.29
• 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：

  6,8,9-tris-benzyloxy-3-phenyl-2,4-dioxa-bicyclo[3.3.1]nonan-7-ol 在 偶氮二异丁腈 、 三正丁基氢锡 、 sodium hydride 作用下， 以 四氢呋喃 、 甲苯 、 mineral oil 为溶剂， 反应 30.0h， 生成 1,3-O-benzylidene-2,4,6-tri-o-benzyl-5-deoxy-myo-inositol
  参考文献：
  名称：

  Thermal epimerization of inositol 1,3-benzylidene acetals in the molten state

  摘要：

  1,3-O-Benzylidene-2,4,5,6-tetra-O-substituted-myo-inositol derivatives obtained by the DIBAL-H reduction of the corresponding myo-inositol 1,3,5-orthobenzoate derivatives undergo epimerization at the acetal carbon on heating, in the molten state, just above their melting point. The same epimerization reaction does not proceed either in the crystalline state or in solution. DFT calculations suggest that the epimeric acetal obtained by this thermal process is relatively more stable than the starting acetal. Either of these acetals could not be obtained by the reaction of the corresponding inositol derived diol with benzaldehyde. These observations constitute a novel reaction solely in the molten state, which are rarely encountered in the literature. X-ray crystal structures of the epimeric acetals as well as their radical deoxygenation reaction are also reported. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2011.07.044
• 作为产物：
  描述：

  溴甲苯 在 lithium hydride 、 二异丁基氢化铝 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 3.0h， 生成 6,8,9-tris-benzyloxy-3-phenyl-2,4-dioxa-bicyclo[3.3.1]nonan-7-ol
  参考文献：
  名称：

  Thermal epimerization of inositol 1,3-benzylidene acetals in the molten state

  摘要：

  1,3-O-Benzylidene-2,4,5,6-tetra-O-substituted-myo-inositol derivatives obtained by the DIBAL-H reduction of the corresponding myo-inositol 1,3,5-orthobenzoate derivatives undergo epimerization at the acetal carbon on heating, in the molten state, just above their melting point. The same epimerization reaction does not proceed either in the crystalline state or in solution. DFT calculations suggest that the epimeric acetal obtained by this thermal process is relatively more stable than the starting acetal. Either of these acetals could not be obtained by the reaction of the corresponding inositol derived diol with benzaldehyde. These observations constitute a novel reaction solely in the molten state, which are rarely encountered in the literature. X-ray crystal structures of the epimeric acetals as well as their radical deoxygenation reaction are also reported. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2011.07.044

文献信息

• Intramolecular Hydrogen Abstraction in Radicals Derived from Inositol 1,3-Acetals: Efficient Access to Cyclitols
  作者：Chebrolu Murali、Bharat P. Gurale、Mysore S. Shashidhar

  DOI：10.1002/ejoc.200901156

  日期：2010.2

  used to prepare neo-inositol and isomeric deoxy-amino inositols. Most of the reactions in these synthetic sequences starting from myo-inositol give one product in each step. The results presented here show that myo-inositol 1,3,5-orthobenzoate offers many advantages over other orthoesters for the synthesis of cyclitol derivatives from myo-inositol.

  通过裂解肌醇 1,3,5-邻苯甲酸酯中的原苯甲酸酯部分获得的亚苄基缩醛用于通过其黄原酸酯制备单脱氧肌醇衍生物和二脱氧肌醇衍生物。双脱氧是亚苄基缩醛氢分子内提取和缩醛环随后裂解的结果。这种裂解不会发生在衍生自其他原酸酯的类似缩醛中。来自肌醇 1,3,5-原酸酯的 1,3-缩醛也用于制备新肌醇和异构脱氧氨基肌醇。这些合成序列中从肌醇开始的大多数反应在每个步骤中都会产生一种产物。此处显示的结果表明，肌醇 1,3,5-原苯甲酸酯在从肌醇合成环醇衍生物方面比其他原酸酯具有许多优势。
• Hydroxyl group deprotection reactions with Pd(OH)2/C: a convenient alternative to hydrogenolysis of benzyl ethers and acid hydrolysis of ketals
  作者：Chebrolu Murali、Mysore S. Shashidhar、Chinnakonda S. Gopinath

  DOI：10.1016/j.tet.2007.02.096

  日期：2007.5

  Benzyl ethers, ketals and orthoformates were cleaved with Pd(OH)2/C in methanol, to generate the corresponding alcohol; carboxylic acid esters were stable under these reaction conditions. Pd(OH)2/C in methanol was used for the deprotection of hydroxyl groups during the preparation of sequoyitol via myo-inositol orthobenzoate. This method of deprotection has the potential to be useful in the synthesis

  苯甲醚，缩酮和正甲酸酯在甲醇中用Pd（OH）2 / C裂解，生成相应的醇；在这些反应条件下，羧酸酯是稳定的。甲醇中的Pd（OH）2 / C用于通过肌肌醇原苯甲酸酯制备角豆糖醇过程中的羟基脱保护。该脱保护方法具有潜力用于合成不同种类的有机化合物，因为反应条件不涉及强酸，碱或氢。