3-ethyl-4-nitrobenzoyl chloride | 1286687-36-2

• 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: 3-ethyl-4-nitrobenzoyl chloride
• CAS: 1286687-36-2
• 化学式: C₉H₈ClNO₃
• 分子量: 213.62
• InChiKey: MCUJXGFZTXZVAQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  14
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  62.9
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  3-ethyl-4-nitrobenzoyl chloride 在 palladium 10% on activated carbon 、 氢气 、 三乙胺 作用下， 以 乙醇 、 N,N-二甲基甲酰胺 为溶剂， 20.0 ℃ 、303.99 kPa 条件下， 反应 4.0h， 生成 methyl 1-(4-amino-3-ethylbenzoyl)piperidine-4-carboxylate
  参考文献：
  名称：

  Structure-Based Selectivity Optimization of Piperidine–Pteridine Derivatives as Potent Leishmania Pteridine Reductase Inhibitors

  摘要：

  The upregulation of pteridine reductase (PTR1) is a major contributor to antifolate drug resistance in Leishmania spp., as it provides a salvage pathway that bypasses dihydrofolate reductase (DHFR) inhibition. The structure-based optimization of the PTR1 inhibitor methyl-1-[4-(2,4-diaminopteridin-6-ylmethylamino)benzoyl]-piperidine-4-carboxylate (1) led to the synthesis of a focused compound library which showed significantly improved selectivity for the parasite's folate-dependent enzyme. When used in combination with pyrimethamine, a DHFR inhibitor, a synergistic effect was observed for compound 5b. This work represents a step forward in the identification of effective antileishmania agents.

  DOI：

  10.1021/jm300563f
• 作为产物：
  描述：

  3-ethyl-4-nitrobenzoic acid 在 氯化亚砜 作用下， 反应 6.0h， 以93%的产率得到3-ethyl-4-nitrobenzoyl chloride
  参考文献：
  名称：

  Structure-Based Selectivity Optimization of Piperidine–Pteridine Derivatives as Potent Leishmania Pteridine Reductase Inhibitors

  摘要：

  The upregulation of pteridine reductase (PTR1) is a major contributor to antifolate drug resistance in Leishmania spp., as it provides a salvage pathway that bypasses dihydrofolate reductase (DHFR) inhibition. The structure-based optimization of the PTR1 inhibitor methyl-1-[4-(2,4-diaminopteridin-6-ylmethylamino)benzoyl]-piperidine-4-carboxylate (1) led to the synthesis of a focused compound library which showed significantly improved selectivity for the parasite's folate-dependent enzyme. When used in combination with pyrimethamine, a DHFR inhibitor, a synergistic effect was observed for compound 5b. This work represents a step forward in the identification of effective antileishmania agents.

  DOI：

  10.1021/jm300563f

文献信息

• Friedel-Crafts acylation for the synthesis of aryl- and heteroaryl-(3-ethyl-4-nitrophenyl)-methanones
  申请人：Knipp Bernhard

  公开号：US20110087013A1

  公开（公告）日：2011-04-14

  The present invention concerns a synthesis process comprising the following steps (i) reacting 3-ethyl-4-nitrobenzoic acid with thionyl chloride to produce a 3-ethyl-4-nitrobenzoic acid chloride or a 3-ethyl-4-nitrobenzoic acid anhydride from 3-ethyl-4-nitrobenzoic acid by means of water cleavage and (ii) Friedel-Crafts acylation by reacting the 3-ethyl-4-nitrobenzoic acid chloride or the 3-ethyl-4-nitrobenzoic acid anhydride with an optionally substituted aryl-H to form an optionally substituted (3-ethyl-4-nitrophenyl)-aryl-methanone. In addition the present invention concerns compounds containing (3-ethyl-4-nitrophenyl)-aryl-methanone, characterized in that the optionally substituted aryl is an optionally substituted condensed aromate.

  本发明涉及一种合成过程，包括以下步骤：(i)将3-乙基-4-硝基苯甲酸与氯化亚砜反应，以水解产生3-乙基-4-硝基苯甲酸氯化物或3-乙基-4-硝基苯甲酸酸酐；(ii)通过Friedel-Crafts酰化反应，将3-乙基-4-硝基苯甲酸氯化物或3-乙基-4-硝基苯甲酸酸酐与可选取代的芳基-H反应，形成可选取代的(3-乙基-4-硝基苯基)-芳基甲酮。此外，本发明涉及含有(3-乙基-4-硝基苯基)-芳基甲酮的化合物，其特征在于可选取代的芳基为可选取代的缩合芳香族化合物。
• Diamino compounds and their production method and liquid crystal alignment layers using the compounds
  申请人：CHISSO CORPORATION

  公开号：EP0601813A1

  公开（公告）日：1994-06-15

  The present invention provides diamino compounds useful as polymerisation raw materials for production of liquid crystal alignment layers having excellent voltage holding ratios without development of image-sticking phenomena, a method for producing the compounds and liquid crystal display devices having the liquid crystal alignment layers. The diamino compounds are represented by the general formula (1): wherein R indicates hydrogen or an alkyl group having 1 to 8 carbon atoms, further, X, Y and Z indicate hydrogen, an alkyl group having 1 to 3 carbon atoms or fluorine, respectively, and some or all of them may be the same or different, and the positions of these substitutive groups may be ortho positions or meta positions.

  本发明提供了可用作聚合原料的二氨基化合物，用于生产具有优异的电压保持比且不会产生图像粘连现象的液晶配向层，还提供了生产该化合物的方法以及具有该液晶配向层的液晶显示设备。 二氨基化合物用通式（1）表示： 其中，R 表示氢或具有 1 至 8 个碳原子的烷基，此外，X、Y 和 Z 分别表示氢、具有 1 至 3 个碳原子的烷基或氟，它们中的部分或全部可以相同或不同，这些取代基的位置可以是正位或偏位。
• Diamino compounds and methods for preparing them
  申请人：CHISSO CORPORATION

  公开号：EP0708077A1

  公开（公告）日：1996-04-24

  An object of the invention is to propose diamino compounds expressed by the following general formula (1) which are suitable to obtain a raw material, a polyimide resin, for a liquid crystal aligning film without any image sticking and with a high voltage holding ratio at from a low temperature to a high temperature as well as the preparation thereof: wherein, (a) when R²⁵ being a hydrogen atom and D being , all of R¹¹, R¹², R¹³ and R¹⁴ denote a hydrogen atom, and R²¹, R²², R²³, R²⁴, R³¹, R³², R³³, R³⁴, R⁴¹, R⁴², R⁴³ and R⁴⁴ denote independently each other a hydrogen atom or an alkyl group with 1 to 8 carbon atoms, (b) when R²⁵ being a hydrogen atom and D being , all of R¹¹, R¹², R¹³ and R¹⁴ denote a hydrogen atom, and R²¹ and R³², R²² and R³¹, R²³ and R³⁴, as well as R²⁴ and R³³ are respectively the same atoms or groups and denote independently each other hydrogen atoms or straight-chain or branched alkyl groups with 1 to 8 carbon atoms, and R⁴¹, R⁴², R⁴³, R⁴⁴, R⁵¹, R⁵², R⁵³ and R⁵⁴ denote independently each other a hydrogen atom or an alkyl group with 1 to 8 carbon atoms, (c) when R²⁵ being a hydrogen atom and D being a divalent straight-chain or branched hydrocarbon group with 2 to 30 carbon atoms, R¹¹, R¹², R¹³ and R¹⁴ denote independently a hydrogen atom or a straight-chain or branched alkyl group with 1 to 8 carbon atoms, and R²¹ and R³², R²² and R³¹, R²³ and R³⁴ as well as R²⁴ and R³³ are respectively the same atoms or groups and denote independently each other hydrogen atoms or straight-chain or branched alkyl groups with 1 to 8 carbon atoms, (d) when R²⁵ being a straight-chain or branched alkyl group with 1 to 12 carbon atoms, D denotes a direct bond, an aliphatic group with 1 to 30 carbon atoms, an aromatic group with 6 to 30 carbon atoms, or a divalent hydrocarbon group with 7 to 30 carbon atoms having both an aliphatic group and an aromatic group, R¹¹, R¹², R¹³ and R¹⁴ denote independently a hydrogen atom or a straight-chain or branched alkyl group with 1 to 8 carbon atoms, and R²¹ and R³², R²² and R³¹, R²³ and R³⁴ as well as R²⁴ and R³³ are respectively the same atoms or groups and denote independently each other hydrogen atoms or straight-chain or branched alkyl groups with 1 to 8 carbon atoms.

  本发明的目的是提出由以下通式（1）表示的二氨基化合物及其制备方法，这些化合物适用于获得用于液晶对准膜的原材料--聚酰亚胺树脂，在低温至高温条件下不会产生任何图像粘连，并具有较高的电压保持率： 其中 (a) 当 R²⁵ 是氢原子且 D 是 时，所有R¹¹、R¹²、R¹³和R¹⁴均表示氢原子，而R²¹、R²²、R²³、R²⁴、R³¹、R³²、R³³、R³⁴、R⁴¹、R⁴²、R⁴³和R⁴⁴相互独立地表示氢原子或具有1至8个碳原子的烷基、 (b) 当 R²⁵为氢原子且 D 时，所有 R¹¹、R¹²、R¹³ 和 R¹⁴ 均表示氢原子，R²¹ 和 R³²、R²² 和 R³¹、R²³ 和 R³⁴，以及 R²⁴ 和 R³³ 分别是相同的原子或基团，并各自独立地表示氢原子或具有 1 至 8 个碳原子的直链或支链烷基、和 R⁴¹、R⁴²、R⁴³、R⁴⁴、R⁵¹、R⁵²、R⁵³ 和 R⁵⁴ 相互独立地表示氢原子或具有 1 至 8 个碳原子的烷基、 (c) 当 R²⁵ 为氢原子且 D 为具有 2 至 30 个碳原子的二价直链或支链烃基时，R¹¹、R¹²、R¹³ 和 R¹⁴ 相互独立地表示氢原子或具有 1 至 8 个碳原子的直链或支链烷基、和 R²¹ 和 R³²、R²² 和 R³¹、R²³ 和 R³⁴ 以及 R²⁴ 和 R³³ 分别是相同的原子或基团，并各自独立地表示氢原子或具有 1 至 8 个碳原子的直链或支链烷基、 (d) 当 R²⁵ 是具有 1 至 12 个碳原子的直链或支链烷基时，D 表示直接键、具有 1 至 30 个碳原子的脂肪族基团、具有 6 至 30 个碳原子的芳香族基团或具有 7 至 30 个碳原子且同时具有脂肪族基团和芳香族基团的二价烃基，R¹¹、R¹²、R¹¹、R¹²、R¹³ 和 R¹⁴ 独立地表示氢原子或具有 1 至 8 个碳原子的直链或支链烷基，R²¹ 和 R³²、R²² 和 R³¹、R²³ 和 R³⁴ 以及 R²⁴ 和 R³³ 分别是相同的原子或基团，并独立地表示氢原子或具有 1 至 8 个碳原子的直链或支链烷基。
• Friedel-crafts-acylierung zur Synthese von Aryl- und Heteroaryl-(3-ethyl-4-nitro-phenyl)-Methanonen
  申请人：Roche Diagnostics GmbH

  公开号：EP2311792A1

  公开（公告）日：2011-04-20

  Die vorliegende Erfindung betrifft ein Syntheseverfahren enthaltend die folgenden Schritte (i) Umsetzung von 3-Ethyl-4-nitrobenzoesäure mit Thionylchlorid zur Erzeugung eines 3-Ethyl-4-nitrobenzoesäurechlorids oder mittels Wasserabspaltung aus 3-Ethyl-4-nitrobenzoesäure eines 3-Ethyl-4-nitrobenzoesäureanhydrids und (ii) Friedel-Crafts-Acylierung durch Reaktion des 3-Ethyl-4-nitrobenzoesäurechlorids oder des 3-Ethyl-4-nitrobenzoesäureanhydrids mit gegebenenfalls substituiertem Aryl-H, so dass gegebenenfalls substituiertes (3-Ethyl-4-nitrophenyl)-aryl-methanon entsteht. Darüber hinaus betrifft die vorliegende Erfindung Verbindungen enthaltend (3-Ethyl-4-nitrophenyl)-aryl-methanon, dadurch gekennzeichnet, dass das gegebenenfalls substituierte Aryl ein gegebenenfalls substituierter kondensierter Aromat ist.

  本发明涉及一种合成工艺，包括以下步骤 (i) 3-乙基-4-硝基苯甲酸与亚硫酰氯反应生成 3-乙基-4-硝基苯甲酸氯化物，或通过从 3-乙基-4-硝基苯甲酸中水消去的方法生成 3-乙基-4-硝基苯甲酸酐，以及 (ii) 通过 3-乙基-4-硝基苯甲酸与亚硫酰氯反应进行 Friedel-Crafts 丙烯酸化反应生成 3-乙基-4-硝基苯甲酸酐。(ii) 3-乙基-4-硝基苯甲酸氯化物或 3-乙基-4-硝基苯甲酸酐与任选取代的芳基-H、从而形成任选取代的（3-乙基-4-硝基苯基）芳基甲酮。此外，本发明还涉及含有(3-乙基-4-硝基苯基)芳基甲酮的化合物，其特征在于任选取代的芳基是任选取代的融合芳基。
• US5382688A
  申请人：——

  公开号：US5382688A

  公开（公告）日：1995-01-17