(R)-3-allyl-3-isopropyl-1-methylindolin-2-one | 886225-92-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吲哚及其衍生物
• 英文名称: (R)-3-allyl-3-isopropyl-1-methylindolin-2-one
• 英文别名: (3R)-1-methyl-3-propan-2-yl-3-prop-2-enylindol-2-one
• CAS: 886225-92-9
• 化学式: C₁₅H₁₉NO
• 分子量: 229.322
• InChiKey: QOECGDLKQXFARB-OAHLLOKOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  17
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  20.3
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为产物：
  描述：

  allyl 3-(methyl(phenyl)amino)-3-oxopropanoate 在 tris-(dibenzylideneacetone)dipalladium(0) 、 (R,R)-ANDEN-phenyl Trost ligand 、 copper(II) acetate monohydrate 、 sodium hydride 作用下， 以 四氢呋喃 、 甲苯 为溶剂， 反应 192.5h， 生成 3-allyl-3-isopropyl-1-methylindolin-2-one 、 (R)-3-allyl-3-isopropyl-1-methylindolin-2-one
  参考文献：
  名称：

  Asymmetric Decarboxylative Allylation of Oxindoles

  摘要：

  An asymmetric decarboxylative palladium-catalyzed allylation of alkyl- and aryl-substituted oxindoles has been developed, enabling the installation of an all-carbon quaternary chiral center at the oxindole 3-position in excellent yields and good to excellent enantioselectivity. An intriguing substrate-dependent reversal in stereoselectivity has been observed, whereby the size of the substituent determines the facial selectivity in the allylation step.

  DOI：

  10.1021/ol201613a

文献信息

• Asymmetric Decarboxylative Allylation of Oxindoles
  作者：Vilius Franckevičius、James D. Cuthbertson、Mark Pickworth、David S. Pugh、Richard J. K. Taylor

  DOI：10.1021/ol201613a

  日期：2011.8.19

  An asymmetric decarboxylative palladium-catalyzed allylation of alkyl- and aryl-substituted oxindoles has been developed, enabling the installation of an all-carbon quaternary chiral center at the oxindole 3-position in excellent yields and good to excellent enantioselectivity. An intriguing substrate-dependent reversal in stereoselectivity has been observed, whereby the size of the substituent determines the facial selectivity in the allylation step.