ethyl 4-bromo-2-nitrophenylpyruvate | 442521-40-6

• 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: ethyl 4-bromo-2-nitrophenylpyruvate
• 英文别名: ethyl 3-(4-bromo-2-nitrophenyl)-2-oxopropanoate；Benzenepropanoic acid, 4-romo-2-itro--xo-, ethyl ester
• CAS: 442521-40-6
• 化学式: C₁₁H₁₀BrNO₅
• 分子量: 316.108
• InChiKey: KETZUPRZMAWENN-UHFFFAOYSA-N

物化性质

• 沸点：
  408.6±35.0 °C(Predicted)
• 密度：
  1.577±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  18
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  89.2
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  ethyl 4-bromo-2-nitrophenylpyruvate 在 palladium on activated charcoal 吡啶 、 bis-triphenylphosphine-palladium(II) chloride 、 copper(l) iodide 、 锂硼氢 、 氢气 、 乙酸酐 、 N,N,N-trimethylbenzenemethanaminium dichloroiodate 、 三乙胺 、 calcium carbonate 作用下， 以 四氢呋喃 、 乙醇 、 二氯甲烷 为溶剂， 50.0 ℃ 、101.33 kPa 条件下， 反应 24.5h， 生成 [2-Acetyloxy-3-(2-formamido-5-iodo-4-pentylphenyl)propyl] acetate
  参考文献：
  名称：

  Synthesis, conformation and PKC isozyme surrogate binding of new lactone analogues of benzolactam-V8s

  摘要：

  To investigate the role of the amide hydrogen of benzolactam-V8s (1-3) on protein kinase C (PKC) isozyme binding, new lactone analogues of benzolactam-V8s with hydrophobic side chains at positions 8 and/or 9 (5-8) were synthesized. The PKC binding affinities of 8- and 9-decylbenzolactone-V8 (5,6) were much lower than those of 8- and 9-decylbenzolactam-V8 (2,3), respectively, indicating that the amide hydrogen of benzolactam-V8s plays a critical role in PKC binding. 8-Decylbenzolactam-V8 (2) showed lower binding affinities to all PKC isozymes compared with those of 9-decylbenzolactam-V8 (3). The binding affinities of 8-substituted benzolactones (5,7,8) were also lower than those of 9-decylbenzolactone-V8 (6), but their PKC isozyme selectivity was higher than those of 2, 3 and 6. 8-Decybenzolactone-V8 (5) exhibited the most significant eta-C1B selectivity among the four benzolactones (5-8) synthesized in this study. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(02)00099-6
• 作为产物：
  描述：

  4-溴-2-硝基甲苯 、 草酸二乙酯 在 sodium ethanolate 作用下， 生成 ethyl 4-bromo-2-nitrophenylpyruvate
  参考文献：
  名称：

  Synthesis and some reactions of 6-bromooxindole.

  摘要：

  描述了一种高效合成4-和6-溴吲哚酮的过程，这些化合物之前未被报道，合成原料为6-和4-氨基-2-硝基甲苯，同时还介绍了6-溴吲哚酮转化为3-酰化衍生物的过程。

  DOI：

  10.1248/cpb.33.1414

文献信息

• Screening Methods
  申请人：Lautens Mark

  公开号：US20080039625A1

  公开（公告）日：2008-02-14

  Disclosed are processes for the preparation of 2-substituted indole compounds wherein the 2-substituent comprises an R 4 group, wherein R 4 is selected from the group consisting of monocyclic aromatic, polycyclic aromatic, monocyclic heteroaromatic, polycyclic heteroaromatic, 1° alkyl, and alkenyl, all of which are optionally substituted at one or more substitutable positions with one or more suitable substituents, and wherein R 4 is bonded to the 2-position of the indole ring via a C—C bond; the process comprising reacting an orthogem-dihalovinylaniline compound of the formula (I): wherein Halo comprises Br, Cl, or I; each of the one or more R 1 is independently selected from the group consisting of H, fluoro, lower alkyl, lower alkenyl, lower alkoxy, aryloxy, lower haloalkyl, lower alkenyl, —C(O)O-lower alkyl, monocyclic or polycyclic aryl or heteroaryl moiety, or R 1 is an alkenyl group bonded so to as to form a 4- to 20-membered fused monocycle or polycyclic ring with the indole ring; all of which are optionally substituted with one or more suitable substituents at one or more substitutable positions; R 2 comprises H, alkyl, cycloalkyl, aryl, heteroaryl, aryl-loweralkyl-, or heteroaryl-loweralkyl-, all of which are optionally substituted at one or more substitutable positions with one or more suitable substituents; R 3 comprises H, alkyl, haloalkyl, alkenyl, alkynyl, aryl, heteroaryl, cycloalkyl, heterocycle, aryl-(C 1-6 )alkyl-, or heteroaryl-loweralkyl-, all of which are optionally substituted at one or more substitutable positions with one or more suitable substituents; with an organoboron reagent selected from the group consisting of a boronic ester of R 4 , a boronic acid of R 4 , a boronic acid anhydride of R 4 , a trialkylborane of R 4 and a 9-BBN derivative of R 4 ; in the presence of a base, a palladium metal pre-catalyst and a ligand under reaction conditions effective to form the 2-substituted indole compound. Also disclosed are processes for the preparation of ortho-gem-dihalovinylaniline compounds. Novel compounds prepared by the processes and novel uses of the compounds are likewise disclosed.

  本发明涉及制备2-取代吲哚化合物的方法，其中2-取代基包括R4基团，其中R4从单环芳香族、多环芳香族、单环杂芳族、多环杂芳族、1°烷基和烯基中选择，所有这些基团都可以在一个或多个可替换的位置上用一个或多个适当的取代基替换，并且其中R4通过C-C键与吲哚环的2-位置结合；该方法包括将式（I）的正交二卤代乙烯基苯胺化合物与来自以下组的有机硼试剂反应：其中Halo包括Br、Cl或I；其中一个或多个R1各自独立地选择自H、氟、低烷基、低烯基、低烷氧基、芳氧基、低卤代烷基、低烯基、-C（O）O-低烷基、单环或多环芳基或杂芳基基团，或者R1是一个烯基团，通过与吲哚环形成一个4到20个成员的融合的单环或多环环，所有这些基团都可以在一个或多个可替换的位置上用一个或多个适当的取代基替换；R2包括H、烷基、环烷基、芳基、杂芳基、芳基-低烷基-或杂芳基-低烷基-，所有这些基团都可以在一个或多个可替换的位置上用一个或多个适当的取代基替换；R3包括H、烷基、卤代烷基、烯基、炔基、芳基、杂芳基、环烷基、杂环、芳基-(C1-6)烷基-或杂芳基-低烷基-，所有这些基团都可以在一个或多个可替换的位置上用一个或多个适当的取代基替换；在碱、钯金属预催化剂和配体存在下，以有效的反应条件形成2-取代吲哚化合物。本发明还涉及制备正交二卤代乙烯基苯胺化合物的方法。本发明还涉及通过上述方法制备的新化合物以及化合物的新用途。
• 一种Reissert吲哚合成反应中间体的合成方法
  申请人：江西亚太科技发展有限公司

  公开号：CN115340460A

  公开（公告）日：2022-11-15

  本发明提供了一种Reissert吲哚合成反应中间体的合成方法，属于有机化学领域。本发明提供的Reissert吲哚合成反应中间体的合成方法反应式如下： 包括如下步骤：将化合物1、化合物2、碱以及反应溶剂混合，反应，后处理，即得化合物3以及化合物3’，其中，反应溶剂为乙醇与四氢呋喃的混合溶液。本发明提供的Reissert吲哚合成反应中间体的合成方法能够在保证高收率的前提下，有效缩短反应时间。
• KR101741956
  申请人：——

  公开号：——

  公开（公告）日：——
• [EN] NOVEL COMPOUND, PREPARATION METHOD THEREFOR, AND PHARMACEUTICAL COMPOSITION CONTAINING SAME<br/>[FR] NOUVEAU COMPOSÉ, SON PROCÉDÉ DE PRÉPARATION, ET COMPOSITION PHARMACEUTIQUE LE CONTENANT<br/>[KO] 신규 화합물, 이의 제조방법 및 이를 포함하는 약학 조성물
  申请人：HYUNDAI PHARM CO LTD

  公开号：WO2018021762A1

  公开（公告）日：2018-02-01

  본 발명은 CDK5에 의한 PPARγ 인산화를 억제하는 신규 화합물, 이의 제조방법 및 이를 포함하는 약학 조성물에 관한 것으로, 본 발명의 신규 화합물은 PPARγ에 고친화도로 결합하지만 유전자 전사(transcriptional activity)를 유도하지 않아 작용제(agonist)로 작용하지 않고, CDK5의 인산화 작용을 차단하여 종래의 당뇨병 치료제의 부작용이 발생하지 않을 뿐만 아니라, 약리물성이 우수하다. 따라서 본 발명의 화합물을 유효성분으로 포함하는 약학 조성물은 PPARγ 관련 대사성 질환을 치료하는데 유용하게 사용될 수 있다.
• Synthesis, conformation and PKC isozyme surrogate binding of new lactone analogues of benzolactam-V8s
  作者：Yu Nakagawa、Kazuhiro Irie、Akiko Masuda、Hajime Ohigashi

  DOI：10.1016/s0040-4020(02)00099-6

  日期：2002.3

  To investigate the role of the amide hydrogen of benzolactam-V8s (1-3) on protein kinase C (PKC) isozyme binding, new lactone analogues of benzolactam-V8s with hydrophobic side chains at positions 8 and/or 9 (5-8) were synthesized. The PKC binding affinities of 8- and 9-decylbenzolactone-V8 (5,6) were much lower than those of 8- and 9-decylbenzolactam-V8 (2,3), respectively, indicating that the amide hydrogen of benzolactam-V8s plays a critical role in PKC binding. 8-Decylbenzolactam-V8 (2) showed lower binding affinities to all PKC isozymes compared with those of 9-decylbenzolactam-V8 (3). The binding affinities of 8-substituted benzolactones (5,7,8) were also lower than those of 9-decylbenzolactone-V8 (6), but their PKC isozyme selectivity was higher than those of 2, 3 and 6. 8-Decybenzolactone-V8 (5) exhibited the most significant eta-C1B selectivity among the four benzolactones (5-8) synthesized in this study. (C) 2002 Elsevier Science Ltd. All rights reserved.