(Z)-2-(1-allyl-6-bromo-3-(3,7-dimethylocta-2,6-dien-1-yl)-2-oxoindolin-3-yl)acetonitrile

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 异戊烯醇脂质
• 英文名称: (Z)-2-(1-allyl-6-bromo-3-(3,7-dimethylocta-2,6-dien-1-yl)-2-oxoindolin-3-yl)acetonitrile
• 英文别名: 2-[(3S)-6-bromo-3-[(2Z)-3,7-dimethylocta-2,6-dienyl]-2-oxo-1-prop-2-enylindol-3-yl]acetonitrile
• 化学式: C₂₃H₂₇BrN₂O
• 分子量: 427.384
• InChiKey: MASYHVAKXADDDV-RXATWSHQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.7
• 重原子数：
  27
• 可旋转键数：
  8
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.39
• 拓扑面积：
  44.1
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  6-溴靛红 在 sodium tetrahydroborate 、 allyl(cyclopentadiene)palladium(II) 、 sodium hydride 、 N,N-二异丙基乙胺 、 (1R,2R)-(+)-1,2-二氨基环己烷-N,N′-双(2-苯基膦-1-萘酰基) 作用下， 以 1,4-二氧六环 、 甲醇 、 水 、 N,N-二甲基甲酰胺 、 mineral oil 、 苯 为溶剂， 反应 50.17h， 生成 2-(1-allyl-6-bromo-3-(3,7-dimethylocta-1,6-dien-3-yl)-2-oxoindolin-3-yl)acetonitrile 、 (Z)-2-(1-allyl-6-bromo-3-(3,7-dimethylocta-2,6-dien-1-yl)-2-oxoindolin-3-yl)acetonitrile
  参考文献：
  名称：

  Exercising Regiocontrol in Palladium-Catalyzed Asymmetric Prenylations and Geranylation: Unifying Strategy toward Flustramines A and B

  摘要：

  Pd-catalyzed asymmetric prenylation of oxindoles to afford selectively either the prenyl or reverse-prenyl product has been demonstrated. Control of the regioselectivity in this transformation is governed by the choice of ligand, solvent, and halide additive. The resulting prenylated and reverse-prenylated products were transformed into ent-flustramides and ent-flustramines A and B. Additionally, control of the regio- and diastereoselectivity was obtained using pi-geranylpalladium complexes.

  DOI：

  10.1021/ja2020873

文献信息

• Exercising Regiocontrol in Palladium-Catalyzed Asymmetric Prenylations and Geranylation: Unifying Strategy toward Flustramines A and B
  作者：Barry M. Trost、Sushant Malhotra、Walter H. Chan

  DOI：10.1021/ja2020873

  日期：2011.5.18

  Pd-catalyzed asymmetric prenylation of oxindoles to afford selectively either the prenyl or reverse-prenyl product has been demonstrated. Control of the regioselectivity in this transformation is governed by the choice of ligand, solvent, and halide additive. The resulting prenylated and reverse-prenylated products were transformed into ent-flustramides and ent-flustramines A and B. Additionally, control of the regio- and diastereoselectivity was obtained using pi-geranylpalladium complexes.