dimethyl 2-[2-(4-nitrophenylsulfonamido)phenyl]malonate | 1412902-19-2

• 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: dimethyl 2-[2-(4-nitrophenylsulfonamido)phenyl]malonate
• CAS: 1412902-19-2
• 化学式: C₁₇H₁₆N₂O₈S
• 分子量: 408.389
• InChiKey: UTNNNBFPHJLFTR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.83
• 重原子数：
  28.0
• 可旋转键数：
  7.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  141.91
• 氢给体数：
  1.0
• 氢受体数：
  8.0

反应信息

• 作为反应物：
  描述：

  dimethyl 2-[2-(4-nitrophenylsulfonamido)phenyl]malonate 在 tris(dibenzylideneacetone)dipalladium(0) chloroform complex 、 1,3-双(二苯基膦)丙烷 、 potassium carbonate 作用下， 以 四氢呋喃 、 N,N-二甲基甲酰胺 为溶剂， 反应 15.5h， 生成 dimethyl 3-vinyl-2,3-dihydroquinoline-4,4(1H)-dicarboxylate
  参考文献：
  名称：

  Regio- and enantioselective synthesis of functionalized tetrahydroquinolines by palladium-catalyzed cyclization of 2-amidophenylmalonates with allylic bisacetates

  摘要：

  A palladium-catalyzed cyclization of 2-amidophenylmalonates with allylic bisacetates is described. Tetrahydroquinolines having a vinyl group at the 3- or 2-position were produced, in which the regioselectivity of the resulting products was altered depending on the substituent on the amino group. The product was transformed to the azabicyclo[3.3.1]nonene via the ring-closing metathesis. Enantioselective reactions also successfully proceeded in the presence of (S)-BINAP to give the optically active tetrahydroquinoline with high enantioselectivity. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2012.09.075
• 作为产物：
  描述：

  1-氟-2-硝基苯 在 吡啶 、 10% Pd/C 、 potassium tert-butylate 、 氢气 作用下， 以 甲醇 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 20.0~90.0 ℃ 、354.66 kPa 条件下， 反应 6.17h， 生成 dimethyl 2-[2-(4-nitrophenylsulfonamido)phenyl]malonate
  参考文献：
  名称：

  Regio- and enantioselective synthesis of functionalized tetrahydroquinolines by palladium-catalyzed cyclization of 2-amidophenylmalonates with allylic bisacetates

  摘要：

  A palladium-catalyzed cyclization of 2-amidophenylmalonates with allylic bisacetates is described. Tetrahydroquinolines having a vinyl group at the 3- or 2-position were produced, in which the regioselectivity of the resulting products was altered depending on the substituent on the amino group. The product was transformed to the azabicyclo[3.3.1]nonene via the ring-closing metathesis. Enantioselective reactions also successfully proceeded in the presence of (S)-BINAP to give the optically active tetrahydroquinoline with high enantioselectivity. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2012.09.075

文献信息

• Cu(II)/Mn(III)-Promoted Synergistic Radical N-Heteroannulation Reaction: Synthesis of [60]Fullerene-Fused Tetrahydroquinoline Derivatives
  作者：Qingfeng Liu、Tong-Xin Liu、Nana Ma、Chenhao Tu、Ruoya Wang、Guisheng Zhang

  DOI：10.1021/acs.joc.9b00929

  日期：2019.6.7

  Cu(II)/Mn(III)-mediated synergistic radical N-heteroannulation reaction of [60]fullerene with N-sulfonylated o-amino-arylmalonates has been developed for the direct and efficient construction of [60]fullerene-fused tetrahydroquinoline derivatives. A plausible mechanism for the formation of fullerotetrahydroquinolines is proposed, and the electrochemical properties of the obtained fullerene adducts

  已经开发了Cu（II）/ Mn（III）介导的[60]富勒烯与N-磺酰化的邻氨基芳基丙二酸酯的协同自由基N-杂环化反应，用于直接和有效地构建[60]富勒烯稠合的四氢喹啉衍生物。提出了形成全氟四氢喹啉的合理机理，并研究了所得富勒烯加合物的电化学性质。