4-氰基-2-丙基吡啶 | 33744-19-3

• 物质功能分类: 医药中间体 - 杂环化合物
• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡啶及其衍生物
• 中文名称: 4-氰基-2-丙基吡啶
• 中文别名: 2-丙基异烟腈
• 英文名称: 2-propylisonicotinonitrile
• 英文别名: 2-propylpyridine-4-carbonitrile；2-propyl-4-cyanopyridine
• CAS: 33744-19-3
• 化学式: C₉H₁₀N₂
• mdl: MFCD09834373
• 分子量: 146.192
• InChiKey: BYKWSKWKQONOOH-UHFFFAOYSA-N

物化性质

• 沸点：
  106 °C(Press: 14 Torr)
• 密度：
  1.02±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  11
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.333
• 拓扑面积：
  36.7
• 氢给体数：
  0
• 氢受体数：
  2

安全信息

• 海关编码：
  2933399090

制备方法与用途

化学性质：液体。沸点为160℃（5.3kPa，40mmHg）。

用途：丙硫异烟胺的中间体。

生产方法：通过将2-丙基吡啶用过氧化氢氧化生成2-丙基吡啶-N-氧化物；再以三氯氧磷进行氯化得到4-氯-2-丙基吡啶；接着使用焦亚硫酸钠磺化，获得2-丙基吡啶-4-磺酸钠；最后利用氰化钠进行氰化反应制得该产品。

反应信息

• 作为反应物：
  描述：

  4-氰基-2-丙基吡啶 在 palladium on activated charcoal 、 magnesium chloride 作用下， 以 甲醇 、 乙醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 7.08h， 生成 4-(2-(2-propylpyridin-4-yl)thiazol-4-yl)aniline
  参考文献：
  名称：

  Diarylthiazole: An Antimycobacterial Scaffold Potentially Targeting PrrB-PrrA Two-Component System

  摘要：

  Diarylthiazole (DAT), a hit from diversity screening, was found to have potent antimycobacterial activity against Mycobacterium tuberculosis (Mtb). In a systematic medicinal chemistry exploration, we demonstrated chemical opportunities to optimize the potency and physicochemical properties. The effort led to more than 10 compounds with submicromolar MICs and desirable physicochemical properties. The potent antimycobacterial activity, in conjunction with low molecular weight, made the series an attractive lead (antibacterial ligand efficiency (ALE)>0.4). The series exhibited excellent bactericidal activity and was active against drug-sensitive and resistant Mtb. Mutational analysis showed that mutations in prrB impart resistance to DAT compounds but not to reference drugs tested. The sensor kinase PrrB belongs to the PrrBA two component system and is potentially the target for DAT. PrrBA is a conserved, essential regulatory mechanism in Mtb and has been shown to have a role in virulence and metabolic adaptation to stress. Hence, DATs provide an opportunity to understand a completely new target system for antimycobacterial drug discovery.

  DOI：

  10.1021/jm500833f
• 作为产物：
  描述：

  ethyl 2-propylisonicotinate 在 ammonium hydroxide 、 phosphorus pentoxide 作用下， 160.0~170.0 ℃ 、4.0 kPa 条件下， 生成 4-氰基-2-丙基吡啶
  参考文献：
  名称：

  Libermann et al., Bulletin de la Societe Chimique de France, 1958, p. 687,691

  摘要：

  DOI：

文献信息

• Unprotected Amino Acids as Stable Radical Precursors for Heterocycle C–H Functionalization
  作者：Duy N. Mai、Ryan D. Baxter

  DOI：10.1021/acs.orglett.6b01754

  日期：2016.8.5

  of heteroarenes using unprotected amino acids as stable alkyl radical precursors is reported. This one-pot procedure is performed open to air under aqueous conditions and is effective for several natural and unnatural amino acids. Heterocycles of varying structure are suitably functionalized, and reactivity trends reflect the nucleophilic character of the radical species generated.

  据报道，使用未保护的氨基酸作为稳定的烷基自由基前体，可以有效，通用地进行杂芳烃的CH烷基化反应。这种一锅法在水性条件下露天进行，对几种天然和非天然氨基酸均有效。适当地官能化可变结构的杂环，并且反应性趋势反映了所产生的自由基物种的亲核特性。
• [EN] TETRAZOLE DERIVATIVES<br/>[FR] DÉRIVÉS DE TÉTRAZOLE
  申请人：MERCK PATENT GMBH

  公开号：WO2021185793A1

  公开（公告）日：2021-09-23

  The present invention relates to substituted tetrazole derivatives. These compounds are useful for the prevention and/or treatment of several medical conditions including hyperproliferative disorders and diseases.

  本发明涉及替代噻唑酮衍生物。这些化合物对预防和/或治疗包括过度增殖性疾病在内的多种医学状况具有用处。
• [EN] CONDENSED PYRIDINE DERIVASTIVES SUBSTITUED BY AMIDE FUNCTIONS AS ACSS2 INHIBITORS<br/>[FR] DÉRIVÉS DE PYRIDINE CONDENSÉS SUBSTITUÉS PAR DES FONCTIONS AMIDE UTILISÉS EN TANT QU'INHIBITEURS D'ACSS2
  申请人：MERCK PATENT GMBH

  公开号：WO2021185789A1

  公开（公告）日：2021-09-23

  The present invention relates to substituted amide derivatives. These compounds are useful for the prevention and/or treatment of several medical conditions including hyperproliferative disorders and diseases.

  本发明涉及替代酰胺衍生物。这些化合物对预防和/或治疗多种医学状况，包括过度增殖性疾病和疾病，具有一定的用途。
• Light-Induced Alkylation of (Hetero)aromatic Nitriles in a Transition-Metal-Free C–C-Bond Metathesis
  作者：Benjamin Lipp、Alexander Lipp、Heiner Detert、Till Opatz

  DOI：10.1021/acs.orglett.7b00652

  日期：2017.4.21

  cations which undergo a homolytic cleavage of a C(sp3)–C(sp3)-σ-bond rather than the well-known α-C–H-scission. The resulting carbon-centered radicals are used in the ipso-substitution of (hetero)aromatic nitriles proceeding through another single-electron transfer-mediated C–C-bond cleavage and formation.

  光诱导的C–C-σ键易位是通过无过渡金属活化1-苄基1,2,3中未应变的C（sp 3）–C（sp 3）-σ键实现的。 4-四氢异喹啉。这些前体胺的光氧化还原介导的单电子氧化产生自由基阳离子，该阳离子经历C（sp 3）–C（sp 3）-σ键的均质裂解，而不是众所周知的α-C–H断裂。由此产生的以碳为中心的自由基被用于（杂）芳族腈的ipso取代，然后通过另一种单电子转移介导的C–C键裂解和形成。
• Synthesis of Some Anilides of 2-Alkyl-4-pyridinecarboxylic Acids and Their Photosynthesis-Inhibiting Activity
  作者：Miroslav Miletín、Jiří Hartl、Miloš Macháček

  DOI：10.1135/cccc19970672

  日期：——

  Homolytic alkylation of 4-pyridinecarbonitrile with radicals generated by silver nitrate catalyzed oxidative decarboxylation of alkanoic acids and subsequent alkaline hydrolysis afforded 2-alkyl-4-pyridinecarboxylic acids 2a-2e. These were converted into the halogeno-hydroxy substituted anilides 3a-3r via acyl chlorides by reaction with the respective aminophenols at 10 °C. Of the compounds tested, 5-chloro-2-hydroxyphenylamide of 2-butyl-4-pyridinecarboxylic acid 3h showed the highest effect upon oxygen evolution rate in spinach chloroplasts system. The structure-photosynthesis-inhibiting activity relationships are briefly discussed.

  4-吡啶甲腈的同源烷基化通过银硝酸催化氧化脱羧烷酸生成的自由基，随后碱性水解，得到2-烷基-4-吡啶羧酸2a-2e。这些化合物通过与相应的氨基酚在10°C下反应生成酰氯，进而转化为卤代-羟基取代的苯胺3a-3r。在测试的化合物中，2-丁基-4-吡啶羧酸的5-氯-2-羟基苯胺3h在菠菜叶绿体系统中对氧气释放速率影响最大。简要讨论了结构-光合抑制活性关系。