5-bromo-3-hydroxy-1-methyl-3-(2'-oxopropyl)indolin-2-one | 107864-80-2

• 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: 5-bromo-3-hydroxy-1-methyl-3-(2'-oxopropyl)indolin-2-one
• 英文别名: 1-Methyl-3-acetonyl-3-hydroxy-5-bromooxindole；5-Bromo-3-hydroxy-1-methyl-3-(2-oxopropyl)indol-2-one
• CAS: 107864-80-2
• 化学式: C₁₂H₁₂BrNO₃
• 分子量: 298.136
• InChiKey: YDPBGIZTYBKVND-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.1
• 重原子数：
  17
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  57.6
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  5-bromo-3-hydroxy-1-methyl-3-(2'-oxopropyl)indolin-2-one 以 邻二氯苯 为溶剂， 反应 3.0h， 以88%的产率得到5-溴-1-甲基-1H-吲哚-2,3-二酮
  参考文献：
  名称：

  Majumdar, Krishna C.; Kundu, Anup K.; Chatterjee, Pranab, Journal of Chemical Research - Part S, 1996, # 10, p. 460 - 461

  摘要：

  DOI：
• 作为产物：
  描述：

  5-溴-1-甲基-1H-吲哚-2,3-二酮 、 丙酮 在 2,4-二硝基酚 、 (±)-3-methyl-1-morpholinobutan-2-amine 作用下， 以 水 为溶剂， 反应 0.08h， 生成 5-bromo-3-hydroxy-1-methyl-3-(2'-oxopropyl)indolin-2-one
  参考文献：
  名称：

  Organocatalyzed direct asymmetric aldol reaction of isatins in water: low catalyst loading in command

  摘要：

  Simple primary tertiary diamines easily derived from natural primary amino acids have been used to catalyze the aldol reactions in water. The 1 mol % of diamine catalyst is sufficient to catalyze the aldol reaction of cyclohexanone/acetone to isatins provided 3-substituted-3-hydroxy-2-oxindole in good yield and good enantioselectivity. The methodology highlights the importance of low catalyst loading in achieving high enantioselectivity. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2013.04.044

文献信息

• Synthesis and anticonvulsant activity of oximes of 1-R-3-acetonyl-3-hydroxyoxindole and its derivatives
  作者：K. A. Gevorkyan、G. L. Papayan、S. G. Chshmarityan、R. G. Paronikyan、N. E. Akopyan、A. P. Engoyan

  DOI：10.1007/bf00765104

  日期：1987.2
• GEVORKYAN K. A.; PAPAYAN G. L.; CHSHMARITYAN S. G.; PARONIKYAN R. G.; AKO+, XIM.-FARMATS. ZH., 21,(1987) N 2, 167-170
  作者：GEVORKYAN K. A.、 PAPAYAN G. L.、 CHSHMARITYAN S. G.、 PARONIKYAN R. G.、 AKO+

  DOI：——

  日期：——
• Organocatalyzed direct asymmetric aldol reaction of isatins in water: low catalyst loading in command
  作者：Akshay Kumar、Swapandeep Singh Chimni

  DOI：10.1016/j.tet.2013.04.044

  日期：2013.6

  Simple primary tertiary diamines easily derived from natural primary amino acids have been used to catalyze the aldol reactions in water. The 1 mol % of diamine catalyst is sufficient to catalyze the aldol reaction of cyclohexanone/acetone to isatins provided 3-substituted-3-hydroxy-2-oxindole in good yield and good enantioselectivity. The methodology highlights the importance of low catalyst loading in achieving high enantioselectivity. (C) 2013 Elsevier Ltd. All rights reserved.
• Majumdar, Krishna C.; Kundu, Anup K.; Chatterjee, Pranab, Journal of Chemical Research - Part S, 1996, # 10, p. 460 - 461
  作者：Majumdar, Krishna C.、Kundu, Anup K.、Chatterjee, Pranab

  DOI：——

  日期：——