3-oxo-2,3-dihydro-isoxazole-5-carbaldehyde | 5777-21-9

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 3-oxo-2,3-dihydro-isoxazole-5-carbaldehyde
• 英文别名: 3-Oxo-2,3-dihydroisoxazole-5-carbaldehyde；3-oxo-1,2-oxazole-5-carbaldehyde
• CAS: 5777-21-9
• 化学式: C₄H₃NO₃
• mdl: MFCD27665420
• 分子量: 113.073
• InChiKey: MTVFKTPLKNPKCM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.6
• 重原子数：
  8
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  55.4
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  p-methoxybenzyl (6R,7R)-7(Z)-[2-(5-chloro-2-tritylaminothiazol-4-yl)-2-trityloxyiminoacetamido]-3-chloromethyl-3-cephem-4-carboxylate 、 3-oxo-2,3-dihydro-isoxazole-5-carbaldehyde 在 三苯基膦 、 sodium iodide 、 碳酸氢钠 作用下， 以 丙酮 、 二氯甲烷 为溶剂， 生成 (6R,7R)-7-{2-[5-Chloro-2-(trityl-amino)-thiazol-4-yl]-2-[(Z)-trityloxyimino]-acetylamino}-3-[(Z)-2-(3-hydroxy-isoxazol-5-yl)-vinyl]-8-oxo-5-thia-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid 4-methoxy-benzyl ester
  参考文献：
  名称：

  Structural Modifications and Biological Evaluation of 3-Isoxazolylvinylcephalosporins

  摘要：

  Structural modifications and biological evaluations of 3-isoxazolylvinylcephalosporins (I) were performed. The replacement of a hydrogen atom at the 7-aminothiazole group by a chlorine resulted in an improvement: of the activity against resistant Gram-positive bacterial strains including the methicillin-resistant Staphylococcus aureus (MRSA) and the ciprofloxacin-resistant Staphylococcus aureus (CRSA). The introduction of other heterocycles such as an isothiazole or a thiadiazole in place of the isoxazole moiety gave slightly decreased in vitro activities. (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(00)00415-4
• 作为产物：
  描述：

  3-(苄氧基)异噁唑-5-甲醛 在 氢溴酸 作用下， 以 溶剂黄146 为溶剂， 反应 24.0h， 以61%的产率得到3-oxo-2,3-dihydro-isoxazole-5-carbaldehyde
  参考文献：
  名称：

  3-羟基异恶唑保护基团的评估 - 3-烷氧基异恶唑-5-甲醛和 3-羟基异恶唑-5-甲醛（Muscimol 的推定有毒代谢物）的短期访问

  摘要：

  研究了 3-羟基异恶唑-5-酯 1 在 O- 与 N-烷基化方面的区域选择性。3-O-烷基产物 2 受苄基、二苯甲基和烯丙基溴 (≥ 91:9) 的青睐，这与 5-烷基-3-羟基异恶唑的已知用途或使用重氮甲烷（或甲基碘）进行甲基化形成对比. 甲氧基甲基化仅产生 N-取代的异恶唑啉酮 3e。用 DIBAH 还原后，酯 2 得到 3-O-保护的 3-羟基异恶唑-5-甲醛 4 (75-98%)。为了去除苄基保护基团，发现三种变体（HBr/HOAc、H2-Pd/BaSO4、NBS/AIBN）可用于 5-酯、5-甲酰基和 5-羟甲基衍生物。相应地制备了游离 3-羟基-5-甲醛 9，即 GABA 激动剂 muscimol 的假定毒性代谢物。

  DOI：

  10.1002/(sici)1099-0690(199803)1998:3<473::aid-ejoc473>3.0.co;2-v

文献信息

• Studies on Acetylenic Compounds. XLIII. Synthesis of Ibotenic Acid.
  作者：Yukichi Kishida、Tetsuo Hiraoka、Junya Ide、Atsusuke Terada、Norio Nakamura

  DOI：10.1248/cpb.15.1025

  日期：——

  Ibotenic acid (α-amino-3-hydroxy-5-isoxazoleacetic acid monohydrate) (I), a flycidal amino acid isolated from Amanitae fungi, was synthesized. The reaction of ethyl 4, 4-diethoxytetrolate (V) with hydroxylamine in the presence of alkali gave 3-hydroxy-5-isoxazolecarboxaldehyde diethyl acetal (VI), which was hydrolyzed with 50% AcOH to the corresponding 3-hydroxy-5-isoxazolecarboxaldehyde (II). Strecker or Bucherer reaction of II followed by alkaline hydrolysis afforded I, which was identical with the natural ibotenic acid.

  Ibotenic acid（α-氨基-3-羟基-5-异恶唑乙酸一水合物）（I）是从天蝇科真菌中分离出来的一种杀蝇氨基酸。4，4-二乙氧基四甲酸乙酯（V）与羟胺在碱存在下反应生成 3-羟基-5-异恶唑甲醛二乙缩醛（VI），用 50%的 AcOH 将其水解为相应的 3-羟基-5-异恶唑甲醛（II）。对 II 进行 Strecker 或 Bucherer 反应，然后进行碱性水解，可得到 I，它与天然的异烟酸相同。
• Studies on Novel 3-lsoxazolylvinylcephalosporins: II. Synthesis and Biological Activity of 7-(2-(2-Aminothiazol-4-yl)-2-hydroxyiminoacetamido) Derivatives.
  作者：KYUNG IL CHOI、JOO HWAN CHA、AE NIM PAE、YONG SEO CHO、YOUSEUNG KIM、MOON HO CHANG、SONG HEE PARK、SEUNG YONG PARK、DOYEOB KIM、DAE YOUNG JEONG、YOUNG HEE KIM、JAE YANG KONG、HUN YEONG KOH

  DOI：10.7164/antibiotics.51.1122

  日期：——
• Studies on Novel 3-lsoxazolylvinylcephalosporins: I. Synthesis and Biological Activity of 7-(2-(2-Aminothiazol-4-yl)-2-(alkoxy)-iminoacetamido) Derivatives.
  作者：KYUNG IL CHOI、JOO HWAN CHA、AE NIM PAE、YONG SEO CHO、MOON HO CHANG、HUN YEONG KOH

  DOI：10.7164/antibiotics.51.1117

  日期：——
• Structural Modifications and Biological Evaluation of 3-Isoxazolylvinylcephalosporins
  作者：Ae Nim Pae、Jie Eun Lee、Bo Hyung Kim、Joo Hwan Cha、Hea Yeon Kim、Yong Seo Cho、Kyung Il Choi、Hun Yeong Koh、Eun Lee、Je Hak Kim

  DOI：10.1016/s0040-4020(00)00415-4

  日期：2000.7

  Structural modifications and biological evaluations of 3-isoxazolylvinylcephalosporins (I) were performed. The replacement of a hydrogen atom at the 7-aminothiazole group by a chlorine resulted in an improvement: of the activity against resistant Gram-positive bacterial strains including the methicillin-resistant Staphylococcus aureus (MRSA) and the ciprofloxacin-resistant Staphylococcus aureus (CRSA). The introduction of other heterocycles such as an isothiazole or a thiadiazole in place of the isoxazole moiety gave slightly decreased in vitro activities. (C) 2000 Elsevier Science Ltd. All rights reserved.
• Evaluation of Protecting Groups for 3-Hydroxyisoxazoles − Short Access to 3-Alkoxyisoxazole-5-carbaldehydes and 3-Hydroxyisoxazole-5-carbaldehyde, the Putative Toxic Metabolite of Muscimol
  作者：Regine Riess、Michael Schön、Sabine Laschat、Volker Jäger

  DOI：10.1002/(sici)1099-0690(199803)1998:3<473::aid-ejoc473>3.0.co;2-v

  日期：1998.3

  On reduction with DIBAH, the esters 2 afford 3-O-protected 3-hydroxyisoxazole-5-carbaldehydes 4 (75−98%). For removal of the benzyl protecting groups, three variations (HBr/HOAc, H2-Pd/BaSO4, NBS/AIBN) were found useful with 5-ester, 5-formyl, and 5-hydroxymethyl derivatives. The free 3-hydroxy-5-carbaldehyde 9, the putative toxic metabolite of the GABA agonist muscimol, is prepared accordingly. The

  研究了 3-羟基异恶唑-5-酯 1 在 O- 与 N-烷基化方面的区域选择性。3-O-烷基产物 2 受苄基、二苯甲基和烯丙基溴 (≥ 91:9) 的青睐，这与 5-烷基-3-羟基异恶唑的已知用途或使用重氮甲烷（或甲基碘）进行甲基化形成对比. 甲氧基甲基化仅产生 N-取代的异恶唑啉酮 3e。用 DIBAH 还原后，酯 2 得到 3-O-保护的 3-羟基异恶唑-5-甲醛 4 (75-98%)。为了去除苄基保护基团，发现三种变体（HBr/HOAc、H2-Pd/BaSO4、NBS/AIBN）可用于 5-酯、5-甲酰基和 5-羟甲基衍生物。相应地制备了游离 3-羟基-5-甲醛 9，即 GABA 激动剂 muscimol 的假定毒性代谢物。

表征谱图