3-methylisoxazol-5-ol | 45469-93-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 3-methylisoxazol-5-ol
• 英文别名: Methyl-3-isoxazolol-(5)；3-Methylisoxazolin-5-on；3-methyl-2H-isoxazol-5-one；3-methyl-5-hydroxyisoxazole
• CAS: 45469-93-0
• 化学式: C₄H₅NO₂
• 分子量: 99.0892
• InChiKey: CPWLODRXTMANAL-UHFFFAOYSA-N

物化性质

• 沸点：
  223.3±20.0 °C(Predicted)
• 密度：
  1.236±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.69
• 重原子数：
  7.0
• 可旋转键数：
  0.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  46.26
• 氢给体数：
  1.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  3-methylisoxazol-5-ol 在 sodium ethanolate 作用下， 生成 4-Hydroxy-acetessigsaeure-nitril
  参考文献：
  名称：

  Quilico; Stagno D'Alcontres, Gazzetta Chimica Italiana, 1949, vol. 79, p. 660

  摘要：

  DOI：

文献信息

• Oxazolidinone derivatives, process for their preparation and pharmaceutical compositions containing them
  申请人：Syngenta Limited

  公开号：US20030144263A1

  公开（公告）日：2003-07-31

  Compounds of the formula (I), or a pharmaceutically-acceptable salt, or an in-vivo-hydrolysable ester thereof, 1 wherein, for example, X is —O— or —S—; HET is an optionally substituted C-linked 5-membered heteroaryl ring containing 2 to 4 heteroatoms independently selected from N, O and S; Q is selected from, for example, Q1 and Q2 2 R 2 and R 3 are independently hydrogen or fluoro; T is selected from a range of groups, for example, an N-linked (fully unsaturated) 5-membered heteroaryl ring system or a group of formula (TC5): 3 wherein Rc is, for example, R 13 CO—, R 13 SO 2 — or R 13 CS—; wherein R 13 is, for example, optionally substituted (1-10C)alkyl or R 14 C(O)O(1-6C)alkyl wherein R 14 is optionally substituted (1-10C)alkyl; are useful as antibacterial agents; and processes for their manufacture and pharmaceutical compositions containing them are described.

  式(I)的化合物，或其药学上可接受的盐，或其体内可水解的酯， 其中，例如，X为—O—或—S—； HET是一个可选择的取代的C-连接的含有2到4个异原子（独立选择自N、O和S）的5元杂芳环； Q从Q1和Q2中选择 R2和R3独立地为氢或氟； T从一系列基团中选择，例如，一个N-连接的（完全不饱和的）5元杂芳环系统或式(TC5)的基团： 其中Rc是，例如，R13CO—，R13SO2—或R13CS—； 其中R13是，例如，可选择的取代的(1-10C)烷基或R14C(O)O(1-6C)烷基 其中R14是可选择的取代的(1-10C)烷基；这些化合物可用作抗菌剂；并描述了其制备方法和含有它们的药物组合物。
• Diastereoselective Synthesis of Indolindiones by Formal [5+1] Double Michael Cycloaddition to 4-Cinnamoylpyrrolediones
  作者：Pavel S. Silaichev、Valeriy O. Filimonov、Pavel A. Slepukhin、Michael Rubin、Andrey N. Maslivets

  DOI：10.1002/ejoc.201500141

  日期：2015.4

  An efficient [5+1] double Michael cycloaddition of enolates to 4-cinnamoylpyrrole-2,3-diones was investigated; the reaction allows for the highly diastereoselective assembly of indoline scaffolds with up to three contiguous stereogenic centers.

  研究了烯醇化物与 4-肉桂酰吡咯-2,3-二酮的有效 [5+1] 双迈克尔环加成反应；该反应允许具有多达三个连续立体中心的二氢吲哚支架的高度非对映选择性组装。
• New classes of antibacterial oxazolidinones with C-5, methylene O-Linked heterocyclic side chains
  作者：Michael B Gravestock、David G Acton、Michael J Betts、Michael Dennis、Glenn Hatter、Alexandra McGregor、Michael L Swain、R.Geoffrey Wilson、Lisa Woods、Alan Wookey

  DOI：10.1016/j.bmcl.2003.07.033

  日期：2003.12

  Exploration of the structure-activity relationships of the traditional C-5 acetamidomethyl side chain of the oxazolidonone antibacterials has yielded new, potent series of compounds of which the first examples, the O-linked iosoxazoles are described in detail, leading to the selection of the pre-clinical candidate AZD2563. (C) 2003 Elsevier Ltd. All rights reserved.
• Identification of Novel α4β2-Nicotinic Acetylcholine Receptor (nAChR) Agonists Based on an Isoxazole Ether Scaffold that Demonstrate Antidepressant-like Activity
  作者：Li-Fang Yu、Werner Tückmantel、J. Brek Eaton、Barbara Caldarone、Allison Fedolak、Taleen Hanania、Dani Brunner、Ronald J. Lukas、Alan P. Kozikowski

  DOI：10.1021/jm201301h

  日期：2012.1.26

  There is considerable evidence to support the hypothesis that the blockade of nAChR is responsible for the antidepressant action of nicotinic ligands. The nicotinic acetylcholine receptor (nAChR) antagonist, mecamylamine, has been shown to be an effective add-on in patients that do not respond to selective serotonin reuptake inhibitors. This suggests that nAChR ligands may address an unmet clinical need by providing relief from depressive symptoms in refractory patients. In this study, a new series of nAChR ligands based on an isoxazole-ether scaffold have been designed and synthesized for binding and functional assays. Preliminary structure-activity relationship (SAR) efforts identified a lead compound 43, which possesses potent antidepressant-like activity (1 mg/kg, IP; 5 mg/kg, PO) in the classical mouse forced swim test. Early stage absorption, distribution, metabolism, excretion, and toxicity (ADME-Tox) studies also suggested favorable drug-like properties, and broad screening toward other common neurotransmitter receptors indicated that compound 43 is highly selective for nAChRs over the other 45 neurotransmitter receptors and transporters tested.
• WOLLWEBER H.-J.;WENTRUP C., J. ORG. CHEM., 1985, 50, N 12, 2041-2047
  作者：WOLLWEBER H.-J.、WENTRUP C.

  DOI：——

  日期：——