(1S,5S,6R)-5,6-bis(benzyloxy)-3-((S)-hydroxy(4-nitrophenyl)methyl)-2-oxocyclohex-3-enyl acetate | 1376712-08-1

• 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: (1S,5S,6R)-5,6-bis(benzyloxy)-3-((S)-hydroxy(4-nitrophenyl)methyl)-2-oxocyclohex-3-enyl acetate
• 英文别名: [(1S,5S,6R)-3-[(S)-hydroxy-(4-nitrophenyl)methyl]-2-oxo-5,6-bis(phenylmethoxy)cyclohex-3-en-1-yl] acetate
• CAS: 1376712-08-1
• 化学式: C₂₉H₂₇NO₈
• 分子量: 517.535
• InChiKey: DHIDYPQYAHKQNC-HFEYRCFBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.1
• 重原子数：
  38
• 可旋转键数：
  10
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.24
• 拓扑面积：
  128
• 氢给体数：
  1
• 氢受体数：
  8

反应信息

• 作为产物：
  描述：

  对硝基苯甲醛 、 2L-(2,4/3)-2-O-acetyl-3,4-di-O-benzyl-2,3,4-trihydroxy-5-cyclohexen-1-one 在 二乙基碘化铝 、 水 、 碳酸氢钠 作用下， 以 二氯甲烷 、 甲苯 为溶剂， 反应 8.0h， 以85%的产率得到(1S,5S,6R)-5,6-bis(benzyloxy)-3-((S)-hydroxy(4-nitrophenyl)methyl)-2-oxocyclohex-3-enyl 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

文献信息

• Highly diastereoselective Morita–Baylis–Hillman chemistry: a remote activation effect in the diastereoface selective synthesis of densely functionalized branched cyclic enones from d-glucose
  作者：Vikas Kumar、Partha Ghosal、Pintu Das、Arun K. Shaw

  DOI：10.1016/j.tetasy.2012.03.009

  日期：2012.4

  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.