(1S,5S,6R)-5,6-bis(benzyloxy)-3-((R)-(2,3-dichlorophenyl)-(hydroxy)methyl)-2-oxocyclohex-3-enyl 4-nitrobenzoate | 1376712-17-2

• 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-((R)-(2,3-dichlorophenyl)-(hydroxy)methyl)-2-oxocyclohex-3-enyl 4-nitrobenzoate
• CAS: 1376712-17-2
• 化学式: C₃₄H₂₇Cl₂NO₈
• 分子量: 648.496
• InChiKey: KMKFDRHITGYQAQ-RNLCMEEOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.84
• 重原子数：
  45.0
• 可旋转键数：
  11.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  125.2
• 氢给体数：
  1.0
• 氢受体数：
  8.0

反应信息

• 作为产物：
  描述：

  (3S,4S,5R,6S)-4,5-bis(benzyloxy)-6-methoxy-2-methylenetetrahydro-2H-pyran-3-yl 4-nitrobenzoate 在 水 、 mercury(II) trifluoroacetate 、 二乙基碘化铝 、 甲基磺酰氯 、 三乙胺 作用下， 以 二氯甲烷 、 丙酮 、 甲苯 为溶剂， 反应 22.0h， 生成 (1S,5S,6R)-5,6-bis(benzyloxy)-3-((R)-(2,3-dichlorophenyl)-(hydroxy)methyl)-2-oxocyclohex-3-enyl 4-nitrobenzoate
  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