2-{(E)-(S)-1-[(S)-3-Benzyloxy-1-(4-methoxy-benzyloxy)-propyl]-5-hydroxy-3-triethylsilanyl-pent-3-enyloxy}-N,N-dimethyl-acetamide | 612050-90-5

• 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: 2-{(E)-(S)-1-[(S)-3-Benzyloxy-1-(4-methoxy-benzyloxy)-propyl]-5-hydroxy-3-triethylsilanyl-pent-3-enyloxy}-N,N-dimethyl-acetamide
• CAS: 612050-90-5
• 化学式: C₃₃H₅₁NO₆Si
• 分子量: 585.857
• InChiKey: OLCACGMAUWLTOO-DIPVHGOESA-N

物化性质

• 沸点：
  667.3±55.0 °C(predicted)
• 密度：
  1.055±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  6.02
• 重原子数：
  41.0
• 可旋转键数：
  20.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.55
• 拓扑面积：
  77.46
• 氢给体数：
  1.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  2-{(E)-(S)-1-[(S)-3-Benzyloxy-1-(4-methoxy-benzyloxy)-propyl]-5-hydroxy-3-triethylsilanyl-pent-3-enyloxy}-N,N-dimethyl-acetamide 在 四氯化碳 、 三苯基膦 作用下， 反应 0.33h， 以87%的产率得到2-{(E)-(S)-1-[(S)-3-Benzyloxy-1-(4-methoxy-benzyloxy)-propyl]-5-chloro-3-triethylsilanyl-pent-3-enyloxy}-N,N-dimethyl-acetamide
  参考文献：
  名称：

  Total synthesis and determination of the absolute configuration of (+)-neoisoprelaurefucin

  摘要：

  The first total synthesis of the seven-membered ring ether marine natural product (+)-neoisoprelaurefucin (1) has been achieved employing a regioselective internal alkylation of amide 3, a novel sequence for removal of the triethylsilyl group from the resulting triethylsilyloxepene 2, and a bromoetherification of alcohol 16 as key steps. In addition, the absolute stereochemistry of the natural product was assigned. (C) 2003 Published by Elsevier Ltd.

  DOI：

  10.1016/s0040-4039(03)01667-8
• 作为产物：
  描述：

  2-[(E)-(S)-1-[(S)-3-Benzyloxy-1-(4-methoxy-benzyloxy)-propyl]-5-(tetrahydro-pyran-2-yloxy)-3-triethylsilanyl-pent-3-enyloxy]-N,N-dimethyl-acetamide 在 对甲苯磺酸 作用下， 以 甲醇 为溶剂， 反应 0.5h， 以94%的产率得到2-{(E)-(S)-1-[(S)-3-Benzyloxy-1-(4-methoxy-benzyloxy)-propyl]-5-hydroxy-3-triethylsilanyl-pent-3-enyloxy}-N,N-dimethyl-acetamide
  参考文献：
  名称：

  Total synthesis and determination of the absolute configuration of (+)-neoisoprelaurefucin

  摘要：

  The first total synthesis of the seven-membered ring ether marine natural product (+)-neoisoprelaurefucin (1) has been achieved employing a regioselective internal alkylation of amide 3, a novel sequence for removal of the triethylsilyl group from the resulting triethylsilyloxepene 2, and a bromoetherification of alcohol 16 as key steps. In addition, the absolute stereochemistry of the natural product was assigned. (C) 2003 Published by Elsevier Ltd.

  DOI：

  10.1016/s0040-4039(03)01667-8