3-methylbut-2-enoic acid [(1E,3E,5R)-5-{(2R,4E,6E,10S,11S,12E,14S,18E)-10-[(4-methoxybenzyl)oxy]-4-methyl-20-oxo-11,14-bis(triisopropylsilanyloxy)oxacycloicosa-4,6,12,18-tetraen-2-yl}-3-methylhexa-1,3-dienyl]amide | 1191072-38-4

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 大环内酯类和类似物
• 英文名称: 3-methylbut-2-enoic acid [(1E,3E,5R)-5-{(2R,4E,6E,10S,11S,12E,14S,18E)-10-[(4-methoxybenzyl)oxy]-4-methyl-20-oxo-11,14-bis(triisopropylsilanyloxy)oxacycloicosa-4,6,12,18-tetraen-2-yl}-3-methylhexa-1,3-dienyl]amide
• 英文别名: N-[(1E,3E,5R)-5-{(2R,4E,6E,10S,11S,12E,14S,18E)-10-[(4-methoxybenzyl)oxy]-4-methyl-20-oxo-11,14-bis[(tri(propan-2-yl)silyl)oxy]oxacycloicosa-4,6,12,18-tetraen-2-yl}-3-methylhexa-1,3-dien-1-yl]-3-methylbut-2-enamide
• CAS: 1191072-38-4
• 化学式: C₅₈H₉₅NO₇Si₂
• 分子量: 974.566
• InChiKey: QUKSSZASEXOTHT-BDYBKAEKSA-N

物化性质

• 沸点：
  901.4±65.0 °C(predicted)
• 密度：
  1.00±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  15.76
• 重原子数：
  68.0
• 可旋转键数：
  19.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.62
• 拓扑面积：
  92.32
• 氢给体数：
  1.0
• 氢受体数：
  7.0

反应信息

• 作为反应物：
  描述：

  3-methylbut-2-enoic acid [(1E,3E,5R)-5-{(2R,4E,6E,10S,11S,12E,14S,18E)-10-[(4-methoxybenzyl)oxy]-4-methyl-20-oxo-11,14-bis(triisopropylsilanyloxy)oxacycloicosa-4,6,12,18-tetraen-2-yl}-3-methylhexa-1,3-dienyl]amide 在 二甲基硫 、 magnesium bromide ethyl etherate 作用下， 以 二氯甲烷 为溶剂， 反应 0.25h， 以50%的产率得到N-((R,1E,3E)-5-((2R,4E,6E,10S,11S,12E,14S,18E)-10-hydroxy-4-methyl-20-oxo-11,14-bis((triisopropylsilyl)oxy)oxacycloicosa-4,6,12,18-tetraen-2-yl)-3-methylhexa-1,3-dien-1-yl)-3-methylbut-2-enamide
  参考文献：
  名称：

  Catalytic Asymmetric Synthesis of Palmerolide A via Organoboron Methodology

  摘要：

  A catalytic enantioselective synthesis of the antimelanoma marine natural product (-)-palmerolide A was accomplished using a longest sequence of 21 steps and without resorting to stoichiometric chiral auxiliaries or the chiral pool. The right half was constructed with a new variant of the Claisen-Ireland rearrangement exploiting an alkenylboronate as a masked hydroxyl. The left half featured the first application of a diol.SnCl4-catalyzed enantioselective crotylboration in the context of a complex target. This distinct strategy could the way to the design of simplified analogues of palmerolide.

  DOI：

  10.1021/ja906429c
• 作为产物：
  描述：

  、 2-Methyl-1-Propenylmagnesium Bromide 以 四氢呋喃 为溶剂， 反应 0.5h， 以68.8 mg的产率得到3-methylbut-2-enoic acid [(1E,3E,5R)-5-{(2R,4E,6E,10S,11S,12E,14S,18E)-10-[(4-methoxybenzyl)oxy]-4-methyl-20-oxo-11,14-bis(triisopropylsilanyloxy)oxacycloicosa-4,6,12,18-tetraen-2-yl}-3-methylhexa-1,3-dienyl]amide
  参考文献：
  名称：

  Catalytic Asymmetric Synthesis of Palmerolide A via Organoboron Methodology

  摘要：

  A catalytic enantioselective synthesis of the antimelanoma marine natural product (-)-palmerolide A was accomplished using a longest sequence of 21 steps and without resorting to stoichiometric chiral auxiliaries or the chiral pool. The right half was constructed with a new variant of the Claisen-Ireland rearrangement exploiting an alkenylboronate as a masked hydroxyl. The left half featured the first application of a diol.SnCl4-catalyzed enantioselective crotylboration in the context of a complex target. This distinct strategy could the way to the design of simplified analogues of palmerolide.

  DOI：

  10.1021/ja906429c