dimethyl 2-[2-(naphthalene-2-sulfonamido)phenyl]malonate | 1257321-99-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: dimethyl 2-[2-(naphthalene-2-sulfonamido)phenyl]malonate
• CAS: 1257321-99-5
• 化学式: C₂₁H₁₉NO₆S
• 分子量: 413.451
• InChiKey: CYYFUXOGYSNIFO-UHFFFAOYSA-N

物化性质

• 熔点：
  114-115.5 °C
• 沸点：
  566.9±60.0 °C(Predicted)
• 密度：
  1.365±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.07
• 重原子数：
  29.0
• 可旋转键数：
  6.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.14
• 拓扑面积：
  98.77
• 氢给体数：
  1.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  cis-1,4-二乙酰氧基-2-丁烯 、 dimethyl 2-[2-(naphthalene-2-sulfonamido)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 为溶剂， 反应 2.5h， 以55%的产率得到dimethyl-1-(naphthalen-2-ylsulfonyl)-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-(naphthalene-2-sulfonamido)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。
• Highly regioselective synthesis of substituted tetrahydroquinolines by palladium-catalyzed cyclization of substituted 2-amidophenylmalonates with 1,4-diacetoxybut-2-ene
  作者：Masahiro Yoshida、Yohei Maeyama、Kozo Shishido

  DOI：10.1016/j.tetlet.2010.09.033

  日期：2010.11

  The reaction of 2-amidophenylmalonates with 1,4-diacetoxybut-2-ene in the presence of a palladium catalyst is described. Substituted tetrahydroquinolines having a vinyl group at the 3- or 2-position were synthesized, in which the regioselectivities of the double allylic substitution reactions have been altered depending on the substituent on the amino group. Crown Copyright (C) 2010 Published by Elsevier Ltd. All rights reserved.