2-(3-吡啶基)-1,3,4-恶二唑 | 65943-95-5

• 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: 2-(3-吡啶基)-1,3,4-恶二唑
• 中文别名: 3-(1,3,4-噁二唑-2-基)吡啶；2-(3-吡啶基)-1,3,4-噁二唑
• 英文名称: 2-(pyridin-3-yl)-1,3,4-oxadiazole
• 英文别名: 2-pyridin-3-yl-1,3,4-oxadiazole
• CAS: 65943-95-5
• 化学式: C₇H₅N₃O
• mdl: MFCD00816745
• 分子量: 147.136
• InChiKey: WKTRMACWCCVROF-UHFFFAOYSA-N

物化性质

• 熔点：
  75-76 °C(Solv: ethyl acetate (141-78-6); ligroine (8032-32-4))
• 沸点：
  291.5±42.0 °C(Predicted)
• 密度：
  1.255

计算性质

• 辛醇/水分配系数(LogP)：
  0.3
• 重原子数：
  11
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  51.8
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2-(3-吡啶基)-1,3,4-恶二唑 在 sodium t-butanolate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 8.0h， 以93%的产率得到3-氰基吡啶
  参考文献：
  名称：

  A Base-Induced Ring-Opening Process of 2-Substituted-1,3,4-Oxadiazoles for the Generation of Nitriles at Room Temperature

  摘要：

  A novel base-catalysed 1,3,4-oxadiazole fragmentation for the synthesis of nitriles at room temperature has been developed. This reaction is performed under transition-metal-free conditions, and provides a new ring cleavage reaction of 1,3,4-oxadiazoles in organic synthesis.

  DOI：

  10.3184/174751914x14007780679741
• 作为产物：
  描述：

  烟酸乙酯 在 一水合肼 作用下， 以 乙醇 为溶剂， 生成 2-(3-吡啶基)-1,3,4-恶二唑
  参考文献：
  名称：

  Transition metal-free direct C–H bond thiolation of 1,3,4-oxadiazoles and related heteroarenes

  摘要：

  开发了一种便捷的无过渡金属催化方法，利用二芳基二硫醚直接对1,3,4-噁二唑C-H键进行硫醇化。该方法同样适用于吲哚、苯并噻唑、N-苯基苯并咪唑及咖啡因等多种底物，能以良好至优异的产率得到相应的硫醇化产物。

  DOI：

  10.1039/c2cc36711d

文献信息

• SUBSTITUTED BRIDGED UREA ANALOGS AS SIRTUIN MODULATORS
  申请人：GLAXOSMITHKLINE LLC

  公开号：US20150152108A1

  公开（公告）日：2015-06-04

  The present invention relates to novel substituted bridged urea compounds, corresponding related analogs, pharmaceutical compositions and methods of use thereof. Sirtuin-modulating compounds of the present invention may be used for increasing the lifespan of a cell, and treating and/or preventing a wide variety of diseases and disorders, which include, but are not limited to, for example, diseases or disorders related to aging or stress, diabetes, obesity, neurodegenerative diseases, cardiovascular disease, blood clotting disorders, inflammation, cancer, and/or flushing as well as diseases or disorders that would benefit from increased mitochondrial activity. The present invention also related to compositions comprising a sirtuin-modulating compound in combination with another therapeutic agent.

  本发明涉及新型取代桥式脲化合物，相应的相关类似物，药物组合物以及其使用方法。本发明的抑制素调节化合物可用于延长细胞寿命，并治疗和/或预防各种疾病和疾病，包括但不限于与衰老或压力、糖尿病、肥胖、神经退行性疾病、心血管疾病、血液凝块疾病、炎症、癌症和/或潮红有关的疾病或疾病，以及那些会受益于增加线粒体活性的疾病或疾病。本发明还涉及包含抑制素调节化合物与另一治疗剂组合的组合物。
• Electrophilic activation of nitroalkanes in efficient synthesis of 1,3,4-oxadiazoles
  作者：Alexander V. Aksenov、Vladislav Khamraev、Nicolai A. Aksenov、Nikita K. Kirilov、Dmitriy A. Domenyuk、Vladimir A. Zelensky、Michael Rubin

  DOI：10.1039/c9ra00976k

  日期：——

  A novel methodology for general and chemoselective preparation of non-symmetric 1,3,4-oxadiazoles is developed. This unusual reaction proceeds via polyphosphoric acid-assisted activation of nitroalkanes towards nucleophilic attack with acylhydrazides.

  开发了一种用于非对称 1,3,4-恶二唑的通用和化学选择性制备的新方法。这种不寻常的反应是通过多磷酸辅助的硝基烷烃活化向酰基肼的亲核攻击而进行的。
• Palladium-Catalyzed Decarboxylative Cross-Coupling of 1,3,4-Oxa­diazoles with Alkynoic Acids: A Simple Route for the Preparation of 2-Alkynylated 1,3,4-Oxadiazoles
  作者：Ch. Reddy、L. Reddy、P. Reddy

  DOI：10.1055/s-0036-1588115

  日期：——

  4-oxadiazole derivatives have been synthesized by the decarboxylative cross-coupling of alk-2-ynoic acids with 2-(het)aryl-1,3,4-oxadiazoles, employing palladium(II) chloride as the catalyst and silver(I) oxide as an oxidant with 1,3-bis(diphenylphosphanyl)propane as a ligand. Products were formed in high yields with no byproduct. For the first time 2-alk-1-ynyl-5-(het)aryl-1,3,4-oxadiazole derivatives have

  摘要 首次通过烷-2-炔酸与2-（杂）芳基的脱羧交叉偶联合成了2-alk-1-炔基-5-（杂）芳基-1,3,4-恶二唑衍生物-1,3,4-恶二唑，采用氯化钯（II）作为催化剂，氧化银（I）作为氧化剂，以1,3-双（二苯基膦基）丙烷为配体。产物以高收率形成，没有副产物。 首次通过烷-2-炔酸与2-（杂）芳基的脱羧交叉偶联合成了2-alk-1-炔基-5-（杂）芳基-1,3,4-恶二唑衍生物-1,3,4-恶二唑，采用氯化钯（II）作为催化剂，氧化银（I）作为氧化剂，以1,3-双（二苯基膦基）丙烷为配体。产物以高收率形成，没有副产物。
• [EN] COMPOSITIONS AND METHODS FOR TREATING DISEASES AND CONDITIONS<br/>[FR] COMPOSITIONS ET MÉTHODES POUR LE TRAITEMENT DE MALADIES ET D'ÉTATS PATHOLOGIQUES
  申请人：UNIV PITTSBURGH

  公开号：WO2016094659A1

  公开（公告）日：2016-06-16

  A compound of Formula II, or a salt, ester, solvate, hydrate or prodrug thereof: where: X1 is a branched or unbranched C1-10 alkyl, (CH2)s-NH-(CH2)t, (CH2)s-0-(CH2)t, or (CH2)S-C(NH2)- (CH2)v-NH-(CH2)t,where s, t and v are each, independently an integer from 1 to 5; A and B are each, independently, C6-10 aryl, C6-10aryl-C1-6alkyl, C3-9 heteroaryl, or C3-9heteroaryl-C1- 6alkyl, each optionally substituted with 1, 2 or 3 independently selected Rg groups; C and D are each, independently, C3-7 cycloalkyl, C3-7 cycloalkyl-C1-6alkyl, C3-7 heterocycloalkyl, C3-7 heterocycloalkyl-C1-6 alkyl, C6-10aryl, C6-10aryl-C1-6alkyl, C3-9 heteroaryl, or C3-9heteroaryl-C1-6alkyl, each optionally substituted with 1, 2 or 3 independently selected Rg groups; each Rg is, independently, halogen, C1-6 alkyl, C1-6 haloalkyl, hydroxyl, C1-6 alkoxy, C1-6 haloalkoxy, amino, C1-6alkylamino, or di-C1-6alkylamino; and n1 and p1 are each, independently, integers from 1 to 10.

  Formula II的化合物，或其盐、酯、溶剂合物、水合物或前药：其中：X1是支链或非支链的C1-10烷基，(CH2)s-NH-(CH2)t，(CH2)s-0-(CH2)t，或(CH2)S-C(NH2)-(CH2)v-NH-(CH2)t，其中s、t和v分别是1到5之间的整数；A和B分别是独立的C6-10芳基、C6-10芳基-C1-6烷基、C3-9杂芳基或C3-9杂芳基-C1-6烷基，每个都可以选择性地用1、2或3个独立选择的Rg基团取代；C和D分别是独立的C3-7环烷基、C3-7环烷基-C1-6烷基、C3-7杂环烷基、C3-7杂环烷基-C1-6烷基、C6-10芳基、C6-10芳基-C1-6烷基、C3-9杂芳基或C3-9杂芳基-C1-6烷基，每个都可以选择性地用1、2或3个独立选择的Rg基团取代；每个Rg是独立的卤素、C1-6烷基、C1-6卤代烷基、羟基、C1-6烷氧基、C1-6卤代烷氧基、氨基、C1-6烷基氨基或二C1-6烷基氨基；n1和p1分别是独立的1到10之间的整数。
• Copper‐Catalyzed Enantioconvergent Cross‐Coupling of Racemic Alkyl Bromides with Azole C(sp ² )−H Bonds
  作者：Xiao‐Long Su、Liu Ye、Ji‐Jun Chen、Xiao‐Dong Liu、Sheng‐Peng Jiang、Fu‐Li Wang、Lin Liu、Chang‐Jiang Yang、Xiao‐Yong Chang、Zhong‐Liang Li、Qiang‐Shuai Gu、Xin‐Yuan Liu

  DOI：10.1002/anie.202009527

  日期：2021.1.4

  development of enantioconvergent cross‐coupling of racemic alkyl halides directly with heteroarene C(sp2)−H bonds has been impeded by the use of a base at elevated temperature that leads to racemization. We herein report a copper(I)/cinchona‐alkaloid‐derived N,N,P‐ligand catalytic system that enables oxidative addition with racemic alkyl bromides under mild conditions. Thus, coupling with azole C(sp2)−H bonds

  外消旋烷基卤化物与杂芳烃C（sp 2）-H键直接对映对合交叉偶联的发展已被在高温下使用导致外消旋作用的碱所阻碍。我们在此报告了铜（I）/金鸡纳生物碱衍生的N，N，P配体催化体系，该体系能够在温和条件下与外消旋烷基溴化物进行氧化加成。因此，已经以高对映选择性实现了与吡咯C（sp 2）-H键的偶联，从而提供了许多潜在有用的α-手性烷基化吡咯，例如1,3,4-恶二唑，恶唑和苯并[ d]]恶唑以及1,3,4-三唑，用于药物发现。机理实验表明，在反应条件下，吡咯C（sp 2）-H键容易去质子化，并且涉及烷基自由基。