N(1)-methyl-N(1)-phenyl-N(3),N(3)-dipropylmalonamide | 1373442-85-3

• 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: N(1)-methyl-N(1)-phenyl-N(3),N(3)-dipropylmalonamide
• 英文别名: N-methyl-N-phenyl-N',N'-dipropylpropanediamide
• CAS: 1373442-85-3
• 化学式: C₁₆H₂₄N₂O₂
• 分子量: 276.379
• InChiKey: PFXNXSBQQVDAEL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  20
• 可旋转键数：
  7
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  40.6
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  N(1)-methyl-N(1)-phenyl-N(3),N(3)-dipropylmalonamide 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65%的产率得到2-hydroxy-N(1)-methyl-N(1)-phenyl-N(3),N(3)-dipropylmalonamide
  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-methyl malonanilide 、 二正丙胺 在 N,N'-二环己基碳二亚胺 作用下， 以 二氯甲烷 为溶剂， 以54%的产率得到N(1)-methyl-N(1)-phenyl-N(3),N(3)-dipropylmalonamide
  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

文献信息

• 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.