butyl 3-(2,3-dioxoindolin-1-yl)propanoate | 1315276-04-0

• 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: butyl 3-(2,3-dioxoindolin-1-yl)propanoate
• CAS: 1315276-04-0
• 化学式: C₁₅H₁₇NO₄
• 分子量: 275.304
• InChiKey: NEPSRXWWGMMZLP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.95
• 重原子数：
  20.0
• 可旋转键数：
  6.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  63.68
• 氢给体数：
  0.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  butyl 3-(2,3-dioxoindolin-1-yl)propanoate 、 丙烯腈 在 BF₄^(1-)*C₉H₁₉N₂O⁽¹⁺⁾ 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 作用下， 反应 0.47h， 以89%的产率得到butyl 3-[3-(1-cyanovinyl)-3-hydroxy-2-oxo-2,3-dihydro-1H-indol-1-yl]propanoate
  参考文献：
  名称：

  Highly Efficient Synthesis of Novel Morita-Baylis-Hillman Adducts from Activated Ketones Using a DABCO-Based Hydroxy Ionic Liquid (HIL) as a Recyclable Catalyst-Solvent

  摘要：

  A highly efficient non-imidazolium DABCO-based ionic liquid has been prepared for the synthesis of biologically active Morita-Baylis-Hillman adducts from activated ketones. The results show that the ionic liquid is very efficient in the Morita-Baylis-Hillman reaction due to its operational simplicity, high yields, dual catalyst-solvent properties, and excellent recyclability and reusability. This hydroxy ionic liquid acts as a protic solvent and tertiary amine for the preparation of biologically active compounds from isatin, ninhydrin, 1,2-acenaphthylenequinone, and benzil with high yields and very short reaction times.

  DOI：

  10.1055/s-0031-1290773
• 作为产物：
  描述：

  丙烯酸丁酯 、 靛红 在 三乙烯二胺 、 四丁基溴化铵 作用下， 反应 0.08h， 以68%的产率得到butyl 3-(2,3-dioxoindolin-1-yl)propanoate
  参考文献：
  名称：

  SOLVENT-FREE MICROWAVE MICHAEL ADDITION OF ISATIN AND ANILINE SCHIFF BASE OF ISATIN TO α,β-UNSATURATED ESTERS

  摘要：

  The rapid, simple, microwave-assisted Michael addition of isatin and aniline Schiff base of isatin to a wide variety of alkyl and aryl acrylates in the presence of, tetrabutylammonium bromide (TBAB) and 1,4-diazabicyclo[2.2.2]octane (DABCO), under solvent-free conditions, is presented. Under these conditions the addition of isatin to some of alkyl and aryl acrylates afford both related Baylis-Hillman adducts as minor products and the corresponding Michael adducts as major products. Addition of isatin to ethyl acrylate leads to produce Baylis-Hillman/Michael adduct in good yield. This system dose not work on Michael acceptors of methyl acrylate and methyl methacrylate.

  DOI：

  10.4067/s0717-97072011000100021