异噁唑-5-羧酸乙酯 | 173850-41-4

• 物质功能分类: 化学试剂 - 有机试剂 - 酯类
• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 中文名称: 异噁唑-5-羧酸乙酯
• 中文别名: 异噁唑-5-甲酸乙酯；异恶唑-5-甲酸乙酯
• 英文名称: ethyl isoxazole-5-carboxylate
• 英文别名: 5-isoxazolecarboxylic acid ethyl ester；isoxazole-5-carboxylic acid ethyl ester；ethyl 1,2-oxazole-5-carboxylate
• CAS: 173850-41-4
• 化学式: C₆H₇NO₃
• 分子量: 141.126
• InChiKey: JOWMDIFULFYASV-UHFFFAOYSA-N

物化性质

• 保留指数：
  1067

计算性质

• 辛醇/水分配系数(LogP)：
  0.9
• 重原子数：
  10
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  52.3
• 氢给体数：
  0
• 氢受体数：
  4

安全信息

• 海关编码：
  2934999090
• 危险性防范说明：
  P280,P305+P351+P338
• 危险性描述：
  H302

制备方法与用途

异噁唑-5-甲酸乙酯是一种广泛应用的异恶唑衍生物，因其在药物化学和材料科学中的重要作用而备受关注。它被用于实验室研发和化工医药合成过程中。

制备方法如下：将0.15毫摩尔的炔基肟醚1溶解于5毫升THF中，并加入28毫克（0.3毫摩尔）苯酚及5.8毫克（0.03毫摩尔）AgBF4。在室温下，用干燥管填充硅胶后进行回流反应，搅拌12小时（通过TLC监测）。随后，在减压条件下浓缩反应混合物，并使用制备型TLC（己烷/AcOEt = 3:10）纯化残余物以获得异噁唑-5-甲酸乙酯。

反应信息

• 作为反应物：
  描述：

  异噁唑-5-羧酸乙酯 在 lithium aluminium tetrahydride 作用下， 以 乙醚 为溶剂， 反应 4.0h， 生成 5-羟甲基异恶唑
  参考文献：
  名称：

  [EN] NOVEL ANDROGENS
  [FR] ANDROGENES

  摘要：

  本发明的化合物具有如下结构：其中X为S或SO2；R1为(1C-6C)烷基，(3C-6C)烯基或(3C-6C)炔基，每个基可选择地被(3C-6C)环烷基，羟基，OC(O)(1C-4C)烷基，(1C-4C)氧烷基，卤素，氰基，甲酰基，C(O)(1C-4C)烷基，CO2H，CO2(1C-4C)烷基，C(O)NR5R6，S(O)(1C-4C)烷基或S(O)2(1C-4C)烷基取代；R2为氢，(1C-4C)烷基或C(O)(1C-4C)烷基；R3为苯基，可选择地被(1C-4C)烷基，(1C-4C)氟烷基，(1C-4C)氧烷基，(1C-4C)氟氧烷基，卤素，氰基或硝基取代；或R3为5-或6-成员芳香杂环环结构，可选择地被(1C-4C)烷基，(1C-4C)氟烷基，(1C-4C)氧烷基，卤素或氰基取代；R4为苯基或芳香6-成员杂环，取代基在邻位为1-羟基(1C-4C)烷基，(1C-4C)氧烷基，C(O)(1C-4C)烷基，CO2(1C-4C)烷基，C(O)NH2，氰基，硝基或CH=NOR7，并可选择地进一步被(1C-2C)烷基，(1C-2C)氟烷基或卤素取代；R5为2-吡啶基，可选择地被(1C-2C)烷基，(1C-2C)氟烷基或卤素取代；或R5和R6分别为氢或(1C-4C)烷基；R7为氢或C(O)(1C-4C)烷基；R8，R9，R10分别为氢，(1C-2C)烷基，氟或氯；或其盐或水合物形式。

  公开号：

  WO2005102998A1
• 作为产物：
  描述：

  ethyl 4-phenylmethoxyiminobut-2-ynoate 在 silver tetrafluoroborate 、 苯酚 作用下， 以 四氢呋喃 为溶剂， 反应 7.0h， 以59%的产率得到异噁唑-5-羧酸乙酯
  参考文献：
  名称：

  Silver-catalyzed synthesis of disubstituted isoxazoles by cyclization of alkynyl oxime ethers

  摘要：

  A facile and practical synthesis of 3,5-disubstituted isoxazoles via a silver-catalyzed cyclization and subsequent protonation of alkynyl oxime ethers has been developed. The methodology was successfully applied to the synthesis of a biologically active isoxazolecarboxylic acid. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2011.04.083

文献信息

• [EN] TRICYCLIC HETEROCYCLIC COMPOUNDS<br/>[FR] COMPOSÉS HÉTÉROCYCLIQUES TRICYCLIQUES
  申请人：BRISTOL MYERS SQUIBB CO

  公开号：WO2011059784A1

  公开（公告）日：2011-05-19

  Disclosed are compounds of Formula (I) or stereoisomers or salts thereof, wherein: X1, X2, X3, W, Q1, Q2, and G2 are defined herein. Also disclosed are methods of using such compounds as selective agonists for G protein-coupled receptor S1P1, and pharmaceutical compositions comprising such compounds. These compounds are useful in treating, preventing, or slowing the progression of diseases or disorders in a variety of therapeutic areas, such as autoimmune diseases and vascular disease.

  揭示了Formula (I)的化合物或其立体异构体或盐，其中：X1、X2、X3、W、Q1、Q2和G2在此处被定义。还揭示了将这些化合物用作G蛋白偶联受体S1P1的选择性激动剂的方法，以及包含这些化合物的药物组合物。这些化合物在治疗、预防或减缓多种治疗领域的疾病或疾病的进展方面是有用的，如自身免疫疾病和血管疾病。
• Adenosine receptor ligands and their use in the treatment of disease
  申请人：——

  公开号：US20010027196A1

  公开（公告）日：2001-10-04

  The invention relates to cyclic heteroaromatic compounds, containing at least one nitrogen atom, and to their use in the manufacture of medicaments for the treatment of diseases, related to adenosine receptor modulators, such as Alzheimer's disease, Parkinson's disease, neuroprotection, schizophrenia, anxiety, pain, respiration deficits, depression, asthma, allergic responses, hypoxia, ischaemia, seizure, substance abuse, sedation and they may be active as muscle relaxants, antipsychotics, anti epileptics, anticonvulsants and cardiaprotective agents.

  这项发明涉及含有至少一个氮原子的环状杂芳化合物，以及它们在制造用于治疗与腺苷受体调节剂相关的疾病的药物中的应用，如阿尔茨海默病、帕金森病、神经保护、精神分裂症、焦虑、疼痛、呼吸功能障碍、抑郁症、哮喘、过敏反应、缺氧、缺血、癫痫、物质滥用、镇静，它们可能作为肌肉松弛剂、抗精神病药、抗癫痫药、抗惊厥药和心脏保护剂而具有活性。
• [EN] NOVEL ANDROGENS<br/>[FR] ANDROGENES
  申请人：AKZO NOBEL NV

  公开号：WO2005102998A1

  公开（公告）日：2005-11-03

  The compounds of the subject invention have a structure according to formula I: wherein X is S or SO2; R1 is (1C-6C)alkyl, (3C-6C)alkenyl, or (3C-6C)alkynyl, each optionally subst ituted with (3C-6C)cycloalkyl, OH, OC(O)(1C-4C)alkyl, (1C- 4C)alkoxy, halogen, cyano, formyl, C(O)(1C-4C)alkyl, CO2H, CO2(1C- 4C)alkyl, C(O)NR5R6, S(O)(1C-4C)alkyl or S(O)2(1C-4C)alkyl; R2 is hydrogen, (1C-4C)alkyl or C(O)(1C-4C)alkyl; R3 is a phenyl group optionally substituted with (1C-4C)alkyl, (1C-4C)fluoroalkyl, (1C-4C)alkoxy, (1C-4C)fluoroalkoxy, halogen, cyano or nitro; or R3 is a 5- or 6-membered aromatic heterocyclic ring structure optionally substituted with (1C-4C)alkyl, (1C-4C)fluoroalkyl, (1C-4C)alkoxy, halogen or cyano; R4 is a phenyl group or an aromatic 6-membered heterocycle, substituted at the ortho position with 1-hydroxy(1C-4C)alkyl, (1C-4C)alkoxy, C(O)(1C- 4C)alkyl, CO2(1C-4C)alkyl, C(O)NH2, cyano, nitro, or CH=NOR7, and optionally further substituted with (1C-2C)alkyl, (1C-2C)fluoroalkyl or halogen; R5 is 2-pyridyl optionally substituted with (1C-2C)alkyl, (1C- 2C)fluoroalkyl or halogen; or R5 and R6 are independently hydrogen or (1C-4C)alkyl; R7 is hydrogen or C(O)(1C-4C)alkyl; R8 , R9 , R10 are independently hydrogen, (1C-2C)alkyl, fluoro or chloro; or a salt or hydrate form thereof.

  本发明的化合物具有如下结构：其中X为S或SO2；R1为(1C-6C)烷基，(3C-6C)烯基或(3C-6C)炔基，每个基可选择地被(3C-6C)环烷基，羟基，OC(O)(1C-4C)烷基，(1C-4C)氧烷基，卤素，氰基，甲酰基，C(O)(1C-4C)烷基，CO2H，CO2(1C-4C)烷基，C(O)NR5R6，S(O)(1C-4C)烷基或S(O)2(1C-4C)烷基取代；R2为氢，(1C-4C)烷基或C(O)(1C-4C)烷基；R3为苯基，可选择地被(1C-4C)烷基，(1C-4C)氟烷基，(1C-4C)氧烷基，(1C-4C)氟氧烷基，卤素，氰基或硝基取代；或R3为5-或6-成员芳香杂环环结构，可选择地被(1C-4C)烷基，(1C-4C)氟烷基，(1C-4C)氧烷基，卤素或氰基取代；R4为苯基或芳香6-成员杂环，取代基在邻位为1-羟基(1C-4C)烷基，(1C-4C)氧烷基，C(O)(1C-4C)烷基，CO2(1C-4C)烷基，C(O)NH2，氰基，硝基或CH=NOR7，并可选择地进一步被(1C-2C)烷基，(1C-2C)氟烷基或卤素取代；R5为2-吡啶基，可选择地被(1C-2C)烷基，(1C-2C)氟烷基或卤素取代；或R5和R6分别为氢或(1C-4C)烷基；R7为氢或C(O)(1C-4C)烷基；R8，R9，R10分别为氢，(1C-2C)烷基，氟或氯；或其盐或水合物形式。
• Ru(III)-catalyzed construction of variously substituted quinolines from 2-aminoaromatic aldehydes (ketones) and isoxazoles: Isoxazoles as cyclization reagent and cyano sources
  作者：Di Hu、Chao Pi、Wei Hu、Xiliang Han、Yangjie Wu、Xiuling Cui

  DOI：10.1016/j.cclet.2021.12.072

  日期：2022.8

  N-O bond cleavage and fragmentation. Variously substituted (especially 6- or 7-substituted) quinolines could be easily afforded. This procedure features wide functional group compatibility, efficiency and avoiding toxic cyano source. Meanwhile, this protocol could be successfully applied to scale-up synthesis. Further chemical transformations of 3-cyanoquinoline could give some valuable skeletons, demonstrating

  开发了 Ru(Ⅲ) 催化的 2-氨基芳香醛（酮）和异恶唑的环化反应，得到多种 3-氰基喹啉。值得注意的是，异恶唑通过NO 键断裂和断裂充当环化试剂和无毒氰基源。可以很容易地提供各种取代（尤其是 6 或 7 取代）的喹啉。该程序具有广泛的官能团兼容性、效率和避免有毒氰基源。同时，该协议可以成功地应用于放大合成。3-氰基喹啉的进一步化学转化可以产生一些有价值的骨架，证明其在合成应用中的潜力
• Compounds having anti-hepatitics c virus effect
  申请人：——

  公开号：US20030203948A1

  公开（公告）日：2003-10-30

  It is found out that compounds represented by the formula (I): 1 wherein R 1 is an optionally substituted carbocyclic group or an optionally substituted heterocyclic group; and R 2 and R 3 taken together with the adjacent carbon atom form an optionally substituted heterocyclic group having one or more of oxo and/or thioxo; have an HCV RNA-dependent RNA synthase inhibitory effect.

  已发现由以下式表示的化合物（I）具有HCV RNA依赖的RNA合成酶抑制作用：其中R1是可选择地取代的碳环基团或可选择地取代的杂环基团；而R2和R3与相邻的碳原子结合形成一个含有一个或多个氧代和/或硫代的可选择地取代的杂环基团。