1,3-O-benzylidene-2-O-(4-methoxybenzyl)-4,6-di-O-benzyl-myo-inositol | 1334376-78-1

• 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: 1,3-O-benzylidene-2-O-(4-methoxybenzyl)-4,6-di-O-benzyl-myo-inositol
• 英文别名: 4,6-di-O-benzyl-1,3-O-benzylidene-2-O-(4-methoxybenzyl)-myo-inositol
• CAS: 1334376-78-1
• 化学式: C₃₅H₃₆O₇
• 分子量: 568.667
• InChiKey: FFVOJSANGJXBRE-UECXVQFISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.61
• 重原子数：
  42.0
• 可旋转键数：
  11.0
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  75.61
• 氢给体数：
  1.0
• 氢受体数：
  7.0

反应信息

• 作为反应物：
  描述：

  1,3-O-benzylidene-2-O-(4-methoxybenzyl)-4,6-di-O-benzyl-myo-inositol 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 48.5h， 生成 1,3-O-benzylidene-2-O-(4-methoxybenzyl)-4,6-di-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 、 sodium hydride 、 二异丁基氢化铝 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 、 甲苯 、 mineral oil 为溶剂， 反应 30.67h， 生成 1,3-O-benzylidene-2-O-(4-methoxybenzyl)-4,6-di-O-benzyl-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

文献信息

• Chiral crystals from an achiral molecule: 4,6-di-<i>O</i>-benzyl-1,3-<i>O</i>-benzylidene-2-<i>O</i>-(4-methoxybenzyl)-<i>myo</i>-5-inosose
  作者：Bharat P. Gurale、Rajesh G. Gonnade、Mysore S. Shashidhar

  DOI：10.1107/s0108270112010001

  日期：2012.5.15

  The title achiral compound, C₃₅H₃₄O₇, crystallizes in the chiral monoclinic space groupP2₁. The molecules are densely packed to form a helical assembly along the crystallographic twofold screw axisviaC—H...O and C—H...π interactions. Interestingly, the unit-translated helical chains are loosely connectedviaa rather uncommon edge-to-edge Ph—H...H—Ph short contact (H...H = 2.33 Å).

  标题为 C35H34O7 的非手性化合物在手性单斜空间群 P21 中结晶。通过 C-H...O 和 C-H...π 相互作用，分子沿着晶体学上的双螺旋轴密集排列，形成螺旋状组合。有趣的是，单位翻译螺旋链通过一种相当罕见的边对边 Ph-H...H-Ph 短接触（H...H = 2.33 Å）松散地连接在一起。