5-cyclopropyl-3-hydroxyisoxazole | 17281-37-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 5-cyclopropyl-3-hydroxyisoxazole
• 英文别名: 5-cyclopropyl-3-isoxazolol；5-cyclopropylisoxazol-3-ol；5-cyclopropyl-isoxazol-3-one；5-Cyclopropyl-3-hydroxy-isoxazol；3-Hydroxy-5-cyclopropylisoxazol；5-cyclopropyl-1,2-oxazol-3-one
• CAS: 17281-37-7
• 化学式: C₆H₇NO₂
• 分子量: 125.127
• InChiKey: NKUDCPHXLOHDMN-UHFFFAOYSA-N

物化性质

• 熔点：
  107 °C
• 密度：
  1.383±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.3
• 重原子数：
  9
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  38.3
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  5-cyclopropyl-3-hydroxyisoxazole 、 二甲氨基甲酰氯 以 甲苯 为溶剂， 以14%的产率得到5-cyclopropyl-N,N-dimethyl-3-oxoisoxazole-2(3H)-carboxamide
  参考文献：
  名称：

  3-Oxoisoxazole-2(3H)-carboxamides and isoxazol-3-yl carbamates: Resistance-breaking acetylcholinesterase inhibitors targeting the malaria mosquito, Anopheles gambiae

  摘要：

  To identify potential selective and resistance-breaking mosquitocides against the African malaria vector Anopheles gambiae, we investigated the acetylcholinesterase (AChE) inhibitory and mosquitocidal properties of isoxazol-3-yl dimethylcarbamates (15), and the corresponding 3-oxoisoxazole-2(3H)-dimethylcarboxamide isomers (14). In both series, compounds were found with excellent contact toxicity to wild-type susceptible (G3) strain and multiply resistant (Akron) strain mosquitoes that carry the G119S resistance mutation of AChE. Compounds possessing good to excellent toxicity to Akron strain mosquitoes inhibit the G119S mutant of An. gambiae AChE (AgAChE) with k(i) values at least 10-to 600-fold higher than that of propoxur, a compound that does not kill Akron mosquitoes at the highest concentration tested. On average, inactivation of WT AgAChE by dimethylcarboxamides 14 was 10-20 fold faster than that of the corresponding isoxazol-3-yl dimethylcarbamates 15. X-ray crystallography of dimethylcarboxamide 14d provided insight into that reactivity, a finding that may explain the inhibitory power of structurally-related inhibitors of hormone-sensitive lipase. Finally, human/An. gambiae AChE inhibition selectivities of these compounds were low, suggesting the need for additional structural modification. (C) 2015 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2015.01.026
• 作为产物：
  描述：

  乙基3-环丙基-2-丙炔酸酯 在 sodium hydroxide 、 盐酸羟胺 作用下， 以 甲醇 、 水 为溶剂， 以70%的产率得到5-cyclopropyl-3-hydroxyisoxazole
  参考文献：
  名称：

  Skjaebaek, Niels; Ebert, Bjarke; Falch, Erik, Journal of the Chemical Society. Perkin transactions I, 1995, p. 221 - 226

  摘要：

  DOI：

文献信息

• A Novel Route to 5-Substituted 3-Isoxazolols. Cyclization of <i>N,O-</i>DiBoc β-Keto Hydroxamic Acids Synthesized via Acyl Meldrum's Acids
  作者：Ulrik S. Sørensen、Erik Falch、Povl Krogsgaard-Larsen

  DOI：10.1021/jo991409d

  日期：2000.2.1

  We have found that N, O-diBoc-protected beta-keto hydroxamic acids can be synthesized and cyclized to 5-substituted 3-isoxazolols without formation of any byproduct. We present a novel and versatile three-step procedure in which carboxylic acid derivatives are converted into acyl Meldrum's acids which, upon aminolysis with N, O-bis(tert-butoxycarbonyl)hydroxylamine, lead to the N, O-diBoc-protected

  3-异恶唑醇最通常由β-酮酯和羟胺合成。该环化通常产生主要副产物，相应的5-异恶唑酮。我们已经发现，可以合成N，O-diBoc保护的β-酮异羟肟酸并将其环化成5-取代的3-异恶唑醇，而不会形成任何副产物。我们提出了一种新颖且通用的三步程序，其中将羧酸衍生物转化为酰基麦德鲁姆酸，当与N，O-双（叔丁氧基羰基）羟胺进行氨解后，会生成N，O-diBoc保护的β-酮异羟肟酸。然后，将这些异羟肟酸类似物用盐酸处理后，环化成相应的5-取代的3-异恶唑醇。
• Jacquier,R. et al., Bulletin de la Societe Chimique de France, 1970, p. 2685 - 2690
  作者：Jacquier,R. et al.

  DOI：——

  日期：——
• Sato, Kazuo; Sugai, Soji; Tomita, Kazuo, Agricultural and Biological Chemistry, 1986, vol. 50, # 7, p. 1831 - 1838
  作者：Sato, Kazuo、Sugai, Soji、Tomita, Kazuo

  DOI：——

  日期：——
• Jacquier,R. et al., Bulletin de la Societe Chimique de France, 1970, p. 1978 - 1985
  作者：Jacquier,R. et al.

  DOI：——

  日期：——
• Jacquier,R. et al., Bulletin de la Societe Chimique de France, 1967, p. 3003 - 3004
  作者：Jacquier,R. et al.

  DOI：——

  日期：——