(4S,6S,7R,8R,8aS)-6,7-bis(benzyloxy)-4-(4-cyanophenyl)-2,2-dimethyl-6,7,8,8a-tetrahydro-4H-benzo[d][1,3]dioxin-8-yl acetate | 1376712-18-3

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (4S,6S,7R,8R,8aS)-6,7-bis(benzyloxy)-4-(4-cyanophenyl)-2,2-dimethyl-6,7,8,8a-tetrahydro-4H-benzo[d][1,3]dioxin-8-yl acetate
• 英文别名: [(4S,6S,7R,8R,8aS)-4-(4-cyanophenyl)-2,2-dimethyl-6,7-bis(phenylmethoxy)-6,7,8,8a-tetrahydro-4H-1,3-benzodioxin-8-yl] acetate
• CAS: 1376712-18-3
• 化学式: C₃₃H₃₃NO₆
• 分子量: 539.628
• InChiKey: FTISYTAFUYWLKI-WTOCPUKLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.2
• 重原子数：
  40
• 可旋转键数：
  9
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  87
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为产物：
  描述：

  4-氰基苯甲醛 在 cerium(III) chloride heptahydrate 、 camphor-10-sulfonic acid 、 二乙基碘化铝 作用下， 以 乙醇 、 二氯甲烷 、 丙酮 、 甲苯 为溶剂， 反应 22.5h， 生成 (4S,6S,7R,8R,8aS)-6,7-bis(benzyloxy)-4-(4-cyanophenyl)-2,2-dimethyl-6,7,8,8a-tetrahydro-4H-benzo[d][1,3]dioxin-8-yl acetate
  参考文献：
  名称：

  Highly diastereoselective Morita–Baylis–Hillman chemistry: a remote activation effect in the diastereoface selective synthesis of densely functionalized branched cyclic enones from d-glucose

  摘要：

  A highly diastereoselective C-2 alkylation of sugar derived cyclic enone 1 in the presence of diethylaluminium iodide by utilizing Morita-Baylis-Hillman chemistry is reported. While diethylaluminium iodide was found to be a suitable Lewis acid for this transformation, the widely employed TiCl4 was ineffective. A plausible mechanism, which considered the involvement of a Zimmerman-Traxler type of closed transition state and an orthoester intermediate, has been discussed. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2012.03.009