dimethyl 2-[2-(4-methylphenylsulfonamido)phenyl]malonate | 1210801-41-4

• 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-methylphenylsulfonamido)phenyl]malonate
• 英文别名: o-(p-tosylamido)phenylmalonate；ortho-tosylamidophenyl malonate；Dimethyl 2-[2-[(4-methylphenyl)sulfonylamino]phenyl]propanedioate
• CAS: 1210801-41-4
• 化学式: C₁₈H₁₉NO₆S
• 分子量: 377.418
• InChiKey: DZSACHLWFSNVTI-UHFFFAOYSA-N

物化性质

• 熔点：
  138-139 °C
• 沸点：
  498.6±55.0 °C(Predicted)
• 密度：
  1.324±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  26
• 可旋转键数：
  8
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  107
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  dimethyl 2-[2-(4-methylphenylsulfonamido)phenyl]malonate 在 tris(dibenzylideneacetone)dipalladium(0) chloroform complex 、 1,3-双(二苯基膦)丙烷 、 caesium carbonate 、 magnesium 作用下， 以 1,4-二氧六环 、 甲醇 为溶剂， 反应 0.17h， 生成
  参考文献：
  名称：

  钯催化的[4 + 2]和[5 + 2]环合成四氢喹啉和1,4-苯并恶氮杂烷

  摘要：

  通过钯催化的碳酸炔丙基酯的碳酸环[4 + 2]和[5 + 2]与丙二酸酯系的苯胺和2-氨基苄基醇的合成，已经开发了合成四氢喹啉和1,4-苯并x氮平的一般策略。获得了一系列具有潜在生物活性的六元和七元杂环，收率为好至极好。

  DOI：

  10.1002/ejoc.202000262
• 作为产物：
  描述：

  丙二酸二甲酯 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-methylphenylsulfonamido)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

• Chiral Aminophosphines as Catalysts for Enantioselective Double-Michael Indoline Syntheses
  作者：San N. Khong、Ohyun Kwon

  DOI：10.3390/molecules17055626

  日期：——

  The bisphosphine-catalyzed double-Michael addition of dinucleophiles to electron-deficient acetylenes is an efficient process for the synthesis of many nitrogen-containing heterocycles. Because the resulting heterocycles contain at least one stereogenic center, this double-Michael reaction would be even more useful if an asymmetric variant of the reaction were to be developed. Aminophosphines can also facilitate the double-Michael reaction and chiral amines are more readily available in Nature and synthetically; therefore, in this study we prepared several new chiral aminophosphines. When employed in the asymmetric double-Michael reaction between ortho-tosylamidophenyl malonate and 3-butyn-2-one, the chiral aminophosphines produced indolines in excellent yields with moderate asymmetric induction.

  双膦催化的二核亲核试剂对缺电子乙炔的双Michael加成反应是合成多种含氮杂环的高效过程。由于生成的杂环至少含有一个立体中心，如能开发出该反应的不对称变体，双Michael反应将更加有用。氨基膦也可促进双Michael反应，而天然及合成中手性胺更易获得；因此，本研究中我们制备了几种新型手性氨基膦。在甲苯磺酰胺基苯基丙二酸酯与3-丁炔-2-酮的不对称双Michael反应中，手性氨基膦以良好产率制得吲哚啉，并具有中等程度的手性诱导作用。
• 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。
• 一种[60]富勒烯四氢喹啉衍生物的合成方法
  申请人：河南师范大学

  公开号：CN109988113B

  公开（公告）日：2022-04-12

  本发明公开了一种[60]富勒烯四氢喹啉衍生物的合成方法，以富勒烯C60与取代的N‑磺酰基邻氨基苯丙二酸二甲酯为原料，以氯化铜和水合乙酸锰为催化剂，以碳酸铯为无机碱，以邻二氯苯和乙腈的混合溶液为溶剂，在氮气氛围下于120‑140℃反应制得目标产物[60]富勒烯四氢喹啉衍生物。本发明的合成方法中反应步骤简单，在氯化铜和水合乙酸锰的联合催化下以较高的收率获得了富勒烯四氢喹啉类化合物，催化剂价廉易得，实验方法简单，原子经济性高。
• Diphosphine-Catalyzed Mixed Double-Michael Reaction: A Unified Synthesis of Indolines, Dihydropyrrolopyridines, Benzimidazolines, Tetrahydroquinolines, Tetrahydroisoquinolines, Dihydrobenzo-1,4-oxazines, and Dihydrobenzo-3,1-oxazines
  作者：Vardhineedi Sriramurthy、Ohyun Kwon

  DOI：10.1021/ol100078w

  日期：2010.3.5

  Seven different types of benzannulated N-heterocycles-indolines, dihydropyrrolopyridines, benzimidazolines, dihydrobenzo-3,1-oxazines, benzomorpholines, tetrahydroquinolines, and tetrahydroisoquinolines-can be obtained from simple dinucleophiles and electron-deficient acetylenes in one synthetic step. This powerful methodology was made possible through the use of diphenylphosphinopropane (DPPP) as the catalyst, with acetic acid and sodium acetate used as additives in some cases. The benzannulated N-heterocycles were isolated in excellent yields under mild metal-free conditions; they were purified without the need for aqueous workups.
• 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.