methyl (E)-3-(5-methoxy-2-nitrophenyl)acrylate | 142010-17-1

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 肉桂酸及其衍生物
• 英文名称: methyl (E)-3-(5-methoxy-2-nitrophenyl)acrylate
• 英文别名: methyl (E)-3-(5-methoxy-2-nitrophenyl)prop-2-enoate
• CAS: 142010-17-1
• 化学式: C₁₁H₁₁NO₅
• 分子量: 237.212
• InChiKey: WWKPRKNINBHMBU-ZZXKWVIFSA-N

物化性质

• 沸点：
  402.0±35.0 °C(Predicted)
• 密度：
  1.273±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  17
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  81.4
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  methyl (E)-3-(5-methoxy-2-nitrophenyl)acrylate 在 titanium(III) chloride 、 4-polyvinylpyridine 、 ammonium acetate 、 sodium methylate 作用下， 以 四氢呋喃 、 二氯甲烷 、 水 为溶剂， 生成 1,2,3,4-Tetrahydro-6-methoxy-3-(methoxycarbonyl)-2-oxo-4-quinoline acetic acid, methyl ester
  参考文献：
  名称：

  Synthesis and carbamoylation of 1,2,3,4,5,6-hexahydro-1,3-dimethyl-2,6-methano-1,3-benzodiazocin-8-ol: bridged analogues of physostigmine

  摘要：

  The synthesis and carbamoylation of 2,6-methano-1,3-benzodiazocin-8-ol is described. A one pot silyl-aryl ether to carbamate transformation was developed. The compounds are analogues of the cholinesterase inhibitor physostigmine.

  DOI：

  10.1016/0040-4039(92)88151-t
• 作为产物：
  描述：

  5-甲氧基-2-硝基苯甲醛 生成 methyl (E)-3-(5-methoxy-2-nitrophenyl)acrylate
  参考文献：
  名称：

  Bicycliccarbonyl indole compounds as anti-inflammatory/analgesic agents

  摘要：

  该发明提供了以下公式的化合物：或其药学上可接受的盐，其中A是C1-6烷基或—NR1—；Z是C(═L)R2，或SO2R3；U是CH或N；W和Y分别选择自—CH2—，O，S和—N—R1；m为1、2或3；q和r独立地为0、1或2；X独立地选择自卤素，C1-4烷基，卤代C1-4烷基，羟基，C1-4烷氧基，卤代C1-4烷氧基或类似物；n为1或2；L为氧或硫；R1为氢或C1-4烷基；R2为羟基，C1-6烷基，卤代C1-6烷基，C1-6烷氧基，卤代C1-6烷氧基，C3-7环烷氧基，C1-4烷基(C3-7环烷氧基)，—NR4R5或类似物；R3为C1-6烷基或卤代C1-6烷基；R4和R5独立地选择自氢，C1-6烷基和卤代C1-6烷基。该发明还提供了一种药物组合物，用于治疗前列腺素作为病原体参与的医疗状况。

  公开号：

  US06303628B1

文献信息

• Multibond Forming Tandem Reactions of Anilines via Stable Aryl Diazonium Salts: One-Pot Synthesis of 3,4-Dihydroquinolin-2-ones
  作者：Réka J. Faggyas、Megan Grace、Lewis Williams、Andrew Sutherland

  DOI：10.1021/acs.joc.8b01910

  日期：2018.10.19

  A fast and effective one-pot tandem process that generates Heck coupled products from readily available anilines via stable aryl diazonium tosylate salts was developed. The mild and simple procedure involves rapid formation of aryl diazonium salts using a polymer-supported nitrite reagent and p-tosic acid, followed by a base-free Heck–Matsuda coupling with acrylates and styrenes. Using 2-nitroanilines

  开发了一种快速有效的一锅串联方法，该方法可通过稳定的芳基重氮甲苯磺酸盐从易于获得的苯胺生成Heck偶联产物。温和而简单的步骤涉及使用聚合物负载的亚硝酸盐试剂和对羟基苯甲酸酯快速形成芳基重氮盐-甲苯磺酸，然后与丙烯酸酯和苯乙烯进行无碱Heck-Matsuda偶联。使用2-硝基苯胺作为底物，将一锅串联方法扩展到直接合成3,4-二氢喹啉-2-酮。在这种情况下，经过重氮化和Heck-Matsuda偶联生成肉桂酸甲酯，添加氢气并再利用钯催化剂还原硝基和烯烃氢化，可有效形成3,4-二氢喹啉-2-酮。 。一锅四步法的合成效用通过基于喹啉酮的钠离子通道调节剂的五锅法合成得到了证明。
• 2,3-substituted indole compounds as anti-inflammatory and analgesic agents
  申请人：——

  公开号：US06608070B1

  公开（公告）日：2003-08-19

  This invention provides a compound of the following formula: or the pharmaceutically acceptable salts thereof wherein Z is OH, C1-6 alkoxy, —NR2R3 or heterocycle; Q is selected from the following: (a) an optionally substituted phenyl, (b) an optionally substituted 6-membered monocyclic aromatic group containing one, two, three or four nitrogen atom(s), (c) an optionally substituted 5-membered monocyclic aromatic group containing one heteroatom selected from O, S and N and optionally containing one, two or three nitrogen atom(s) in addition to said heteroatom, (d) an optionally substituted C3-7 cycloalkyl and (e) an optionally substituted benzo-fuzed heterocycle; R1 is hydrogen, C1-4 alkyl or halo; R2 and R3 are independently hydrogen, OH, C1-4 alkoxy, C1-4 alkyl or C1-4 alkyl substituted with halo, OH, C1-4 alkoxy or CN; X is independently selected from H, halo, C1-4 alkyl, halo-substituted C1-4 alkyl, OH, C1-4 alkoxy, halo-substituted C1-4 alkoxy, C1-4 alkylthio, NO2, NH2, di-(C1-4 alkyl)amino and CN; and n is 0, 1, 2, 3 and 4. This invention also provides a pharmaceutical composition useful for the treatment of a medical condition in which prostaglandins are implicated as pathogens.

  这项发明提供了以下式的化合物： 或其药学上可接受的盐，其中Z为OH、C1-6烷氧基、—NR2R3或杂环；Q从以下中选择：(a) 可选择取代的苯基，(b) 可选择取代的含有一个、两个、三个或四个氮原子的6-成员单环芳基，(c) 可选择取代的含有O、S和N中选择的一个杂原子的5-成员单环芳基，并且除所述杂原子外还可选择含有一个、两个或三个氮原子，(d) 可选择取代的C3-7环烷基和(e) 可选择取代的苯并噻吩杂环；R1为氢、C1-4烷基或卤素；R2和R3独立地为氢、OH、C1-4烷氧基、C1-4烷基或用卤素、OH、C1-4烷氧基或CN取代的C1-4烷基；X独立地从H、卤素、C1-4烷基、卤素取代的C1-4烷基、OH、C1-4烷氧基、卤素取代的C1-4烷氧基、C1-4烷基硫醚、NO2、NH2、二-(C1-4烷基)氨基和CN中选择；n为0、1、2、3和4。 这项发明还提供了一种用于治疗前列腺素参与的医疗状况的药物组合物。
• Bicycliccarbonyl indole compounds as anti-inflammatory/analgesic agents
  申请人：Pfizer Inc

  公开号：US06303628B1

  公开（公告）日：2001-10-16

  This invention provides a compound of the following formula: or the pharmaceutically acceptable salts thereof wherein A is C 1-6 alkylene or —NR1—; Z is C(═L)R2, or SO2R3; U is CH or N; W and Y are independently selected from —CH2—, O, S and —N—R1; m is 1, 2 or 3; q and r are independently 0, 1 or 2; X is independently selected from halogen, C1-4 alkyl, halo-substituted C1-4 alkyl, hydroxy, C1-4 alkoxy, halo-substituted C1-4 alkoxy or the like; n is 1 or 2; L is oxygen or sulfur; R1 is hydrogen or C1-4 alkyl; R2 is hydroxy, C1-6alkyl, halo-substituted C1-6 alkyl, C1-6 alkoxy, halo-substituted C1-6 alkoxy, C3-7 cycloalkoxy, C1-4 alkyl(C3-7 cycloalkoxy), —NR4R5 or the like; R3 is C1-6 alkyl or halo-substituted C1-6 alkyl; and R4 and R5 are independently selected from hydrogen, C1-6 alkyl and halo-substituted C1-6alkyl. This invention also provides a pharmaceutical composition useful for the treatment of a medical condition in which prostaglandins are implicated as pathogens.

  该发明提供了以下公式的化合物：或其药学上可接受的盐，其中A是C1-6烷基或—NR1—；Z是C(═L)R2，或SO2R3；U是CH或N；W和Y分别选择自—CH2—，O，S和—N—R1；m为1、2或3；q和r独立地为0、1或2；X独立地选择自卤素，C1-4烷基，卤代C1-4烷基，羟基，C1-4烷氧基，卤代C1-4烷氧基或类似物；n为1或2；L为氧或硫；R1为氢或C1-4烷基；R2为羟基，C1-6烷基，卤代C1-6烷基，C1-6烷氧基，卤代C1-6烷氧基，C3-7环烷氧基，C1-4烷基(C3-7环烷氧基)，—NR4R5或类似物；R3为C1-6烷基或卤代C1-6烷基；R4和R5独立地选择自氢，C1-6烷基和卤代C1-6烷基。该发明还提供了一种药物组合物，用于治疗前列腺素作为病原体参与的医疗状况。
• Synthesis and evaluation of 2-carboxy indole derivatives as potent and selective anti-leukemic agents
  作者：Nathália Moreno Cury、Rebeca Monique Capitão、Renan do Canto Borges de Almeida、Leonardo Luís Artico、Juliana Ronchi Corrêa、Eric Francisco Simão dos Santos、José Andrés Yunes、Carlos Roque Duarte Correia

  DOI：10.1016/j.ejmech.2019.111570

  日期：2019.11

  action and in vivo anti-leukemia efficacy. The synthesis of 3-substituted-2-carboalkoxy indoles relied on two Heck arylations of methyl acrylate and methyl cinnamates respectively, to generate β,β-disubstituted acrylates followed by an efficient Cadogan-Sundberg reaction of these latter intermediates. The method developed led to the synthesis of twenty-one novel functionalized indoles. Of these, indole 20

  尽管在治疗急性淋巴细胞性白血病（ALL）方面取得了成功，但仍非常需要寻找具有针对白血病细胞的选择性和预防复发ALL的功效的新药。在这里，我们描述了几种新颖的3-取代的和3,6-二取代的2-羰基烷氧基吲哚的合成，随后阐明了它们的作用机理和体内抗白血病功效。3-取代的-2-羰基烷氧基吲哚的合成分别依赖于丙烯酸甲酯和肉桂酸甲酯的两次Heck芳基化，以生成β，β-二取代的丙烯酸酯，随后有效地进行这些后者中间体的Cadogan-Sundberg反应。所开发的方法导致了二十一种新型功能化吲哚的合成。其中，吲哚20在纳摩尔水平上显示出对白血病细胞的选择性细胞毒性，因此被选择用于研究其作用机理。发现吲哚20靶向微管蛋白，导致G2 / M细胞周期停滞，DNA损伤和细胞凋亡。吲哚20以时间依赖性方式减少白血病细胞中的β-微管蛋白蛋白，并诱导Hela细胞中微管网络解聚，从而充分表征其微管去稳定剂活性。吲哚20处
• Transition metal complexes in organic synthesis, part 36. Cyclization of tricarbonyliron complexes by oxygen to 4a,9a-dihydro-9H-carbazoles: Application to the synthesis of mukonine, mukonidine, and pyrido[3,2,1-jk]carbazoles
  作者：Hans-Joachim Knölker、Marcus Wolpert

  DOI：10.1016/s0040-4039(96)02364-7

  日期：1997.1

  Aryl-substituted tricarbonyl-(η4-cyclohexa-1,3-diene)iron complexes are oxidatively cyclized in protic medium in the air to tricarbonyliron-complexed 4a,9a-dihydro-9H-carbazoles. The method is applied to the total synthesis of mukonine and mukonidine.

  芳基取代的tricarbonyl-（η 4 -环己-1,3-二烯）合铁络合物在质子介质氧化环化在空中tricarbonyliron络合4a中，9A二氢-9- ħ -carbazoles。该方法适用于粘康宁和粘康定的全合成。