ethyl 3-[methyl(p-tolyl)amino]-3-oxopropanoate | 1373442-12-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: ethyl 3-[methyl(p-tolyl)amino]-3-oxopropanoate
• 英文别名: ethyl 3-(N,4-dimethylanilino)-3-oxopropanoate
• CAS: 1373442-12-6
• 化学式: C₁₃H₁₇NO₃
• 分子量: 235.283
• InChiKey: AJQZCWWHDBPLRE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  17
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  46.6
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  ethyl 3-[methyl(p-tolyl)amino]-3-oxopropanoate 在 [双(三氟乙酰氧基)碘]苯 作用下， 以 2,2,2-三氟乙醇 为溶剂， 以56%的产率得到ethyl 3-hydroxy-1,5-dimethyl-2-oxoindoline-3-carboxylate
  参考文献：
  名称：

  Phenyliodine Bis(trifluoroacetate)-Mediated Oxidative C–C Bond Formation: Synthesis of 3-Hydroxy-2-oxindoles and Spirooxindoles from Anilides

  摘要：

  The reaction of phenyliodine bis(trifluoroacetate) (PIFA) with a series of anilides 1 (E = CO2Et) In CF3CH2OH was found to give 3-hydroxy-2-oxindole derivatives 2, while that with various anilides 1' (E = CON(R-4)Ar) afforded the C-2-symmetric or unsymmetric spirooxindoles 3. These processes feature a metal-free oxidative C(sp(2))-C(sp(3)) bond formation, followed by oxidative hydroxylation or spirocyclization.

  DOI：

  10.1021/ol300418h
• 作为产物：
  描述：

  N-甲基-对甲基苯胺 在 三乙烯二胺 、 N-碘代丁二酰亚胺 、 水 、 palladium diacetate 、 silver nitrate 、 N,N'-二环己基碳二亚胺 作用下， 以 二氯甲烷 、 丙酮 、 乙腈 为溶剂， 反应 21.0h， 生成 ethyl 3-[methyl(p-tolyl)amino]-3-oxopropanoate
  参考文献：
  名称：

  Palladium-Catalyzed Alcoholysis of 3-Iodopropynamides: Selective Synthesis of Carbamoylacetates

  摘要：

  A novel and selective method for the synthesis of carbamoylacetates via the alcoholysis of 3-iodopropynamides has been developed. 3-Iodopropynamides react with alcohols in the presence of palladium(II) acetate and DABCO to afford the corresponding carbamoylacetates in moderate to good yields.

  DOI：

  10.1055/s-0034-1379104

文献信息

• Fast Transition Metal‐Free Synthesis of Functionalized Oxindoles and Dihydroquinoline‐2‐ones Under Microwave Irradiation
  作者：Júlia L. Couto、Milene M. Hornink、Vinicius R. Nascimento、Leandro H. Andrade

  DOI：10.1002/ejoc.202200962

  日期：2022.11.25

  A fast transition metal-free methodology for the synthesis of highly functionalized heterocycles was developed. The exploitation of formamide or N-methylformamide and potassium persulfate under microwave irradiation resulted in a reaction of 10 s. The functionalized oxindoles and dihydroquinoline-2-ones give access to several spirolactones and spiroimides.

  开发了一种用于合成高功能化杂环的快速无过渡金属方法。甲酰胺或N-甲基甲酰胺和过硫酸钾在微波辐射下的开发导致10秒的反应。功能化的羟吲哚和二氢喹啉-2-酮可以生成多种螺内酯和螺酰亚胺。
• Phenyliodine Bis(trifluoroacetate)-Mediated Oxidative C–C Bond Formation: Synthesis of 3-Hydroxy-2-oxindoles and Spirooxindoles from Anilides
  作者：Junwei Wang、Yucheng Yuan、Rui Xiong、Daisy Zhang-Negrerie、Yunfei Du、Kang Zhao

  DOI：10.1021/ol300418h

  日期：2012.5.4

  The reaction of phenyliodine bis(trifluoroacetate) (PIFA) with a series of anilides 1 (E = CO2Et) In CF3CH2OH was found to give 3-hydroxy-2-oxindole derivatives 2, while that with various anilides 1' (E = CON(R-4)Ar) afforded the C-2-symmetric or unsymmetric spirooxindoles 3. These processes feature a metal-free oxidative C(sp(2))-C(sp(3)) bond formation, followed by oxidative hydroxylation or spirocyclization.
• Palladium-Catalyzed Alcoholysis of 3-Iodopropynamides: Selective Synthesis of Carbamoylacetates
  作者：Can-Cheng Guo、Jian-Sheng Tang

  DOI：10.1055/s-0034-1379104

  日期：——

  A novel and selective method for the synthesis of carbamoylacetates via the alcoholysis of 3-iodopropynamides has been developed. 3-Iodopropynamides react with alcohols in the presence of palladium(II) acetate and DABCO to afford the corresponding carbamoylacetates in moderate to good yields.