3-(1,1-dimethylallyl)-3-hydroxy-1,3-dihydroindol-2-one

• 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: 3-(1,1-dimethylallyl)-3-hydroxy-1,3-dihydroindol-2-one
• 英文别名: 3-hydroxy-3-tert-prenyloxindole；(3S)-3-hydroxy-3-(2-methylbut-3-en-2-yl)-1H-indol-2-one
• 化学式: C₁₃H₁₅NO₂
• 分子量: 217.268
• InChiKey: LOBQSLXKLNBTIA-ZDUSSCGKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  16
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  49.3
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  3-(1,1-dimethylallyl)-3-hydroxy-1,3-dihydroindol-2-one 在 lithium hexamethyldisilazane 、 氯化亚砜 作用下， 以 四氢呋喃 为溶剂， 以69%的产率得到3-chloro-3-(1,1-dimethylallyl)-1,3-dihydroindol-2-one
  参考文献：
  名称：

  Protecting-Group-Free Synthesis of 3-tert-Prenylated Oxindoles: Contiguous All-Carbon Quaternary Centers via Tertiary Neopentyl Substitution

  摘要：

  Ruthenium-catalyzed tert-prenylation of isatin 1 occurs efficiently in the absence of N-protecting groups under the conditions of C-C bond-forming transfer hydrogenation employing 1,1-dimethylallene as the prenyl donor. The prenylated adduct, 3-hydroxy-3-tert-prenyl-oxindole 2, is converted to the tertiary neopentyl chloride 3, which participates in nucleophilic substitution by way of an aza-o-xylylene intermediate to furnish adducts 4a-4l. Through tertiary neopentyl substitution, two contiguous all-carbon quaternary centers are established.

  DOI：

  10.1021/ol9018562
• 作为产物：
  描述：

  3-甲基-1,2-丁二烯 、 靛红 在 甲酸 、 C₅₅H₄₆ClOP₃Ru 、 2-(二叔丁基膦)联苯 作用下， 以 四氢呋喃 为溶剂， 反应 21.0h， 以74%的产率得到3-(1,1-dimethylallyl)-3-hydroxy-1,3-dihydroindol-2-one
  参考文献：
  名称：

  Protecting-Group-Free Synthesis of 3-tert-Prenylated Oxindoles: Contiguous All-Carbon Quaternary Centers via Tertiary Neopentyl Substitution

  摘要：

  Ruthenium-catalyzed tert-prenylation of isatin 1 occurs efficiently in the absence of N-protecting groups under the conditions of C-C bond-forming transfer hydrogenation employing 1,1-dimethylallene as the prenyl donor. The prenylated adduct, 3-hydroxy-3-tert-prenyl-oxindole 2, is converted to the tertiary neopentyl chloride 3, which participates in nucleophilic substitution by way of an aza-o-xylylene intermediate to furnish adducts 4a-4l. Through tertiary neopentyl substitution, two contiguous all-carbon quaternary centers are established.

  DOI：

  10.1021/ol9018562

文献信息

• Protecting-Group-Free Synthesis of 3-<i>tert</i>-Prenylated Oxindoles: Contiguous All-Carbon Quaternary Centers via Tertiary Neopentyl Substitution
  作者：Christopher D. Grant、Michael J. Krische

  DOI：10.1021/ol9018562

  日期：2009.10.15

  Ruthenium-catalyzed tert-prenylation of isatin 1 occurs efficiently in the absence of N-protecting groups under the conditions of C-C bond-forming transfer hydrogenation employing 1,1-dimethylallene as the prenyl donor. The prenylated adduct, 3-hydroxy-3-tert-prenyl-oxindole 2, is converted to the tertiary neopentyl chloride 3, which participates in nucleophilic substitution by way of an aza-o-xylylene intermediate to furnish adducts 4a-4l. Through tertiary neopentyl substitution, two contiguous all-carbon quaternary centers are established.