2-异恶唑啉-3-羧酸 | 4485-98-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑啉类
• 中文名称: 2-异恶唑啉-3-羧酸
• 英文名称: 2-isoxazoline-3-carboxylic acid
• 英文别名: Isoxazolin-3-carbonsaeure；3-Carboxy-isoxazolin-(2)；Isoxazolin-carbonsaeure-(3)；4,5-dihydro-isoxazole-3-carboxylic acid；4,5-dihydroisooxazole-3-carboxylic acid；4,5-Dihydro-1,2-oxazole-3-carboxylic acid
• CAS: 4485-98-7
• 化学式: C₄H₅NO₃
• mdl: MFCD19228412
• 分子量: 115.089
• InChiKey: ZYDBNGULYNHMSF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.2
• 重原子数：
  8
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  58.9
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2-异恶唑啉-3-羧酸 在 N,N-二甲基甲酰胺 草酰氯 作用下， 以 二氯甲烷 为溶剂， 反应 0.75h， 生成 4,5-dihydroisooxazole-3-carboxylic acid chloride
  参考文献：
  名称：

  EP1911350

  摘要：

  公开号：
• 作为产物：
  描述：

  2-methoxyisoxazolidine-3,3-dicarboxylic acid dimethyl ester 在 氢氧化钾 作用下， 以 甲醇 为溶剂， 生成 2-异恶唑啉-3-羧酸
  参考文献：
  名称：

  不对称nonbridgehead氮-17 1：完全分离为对映体和chiralic正alkoxyisoxazolidines的绝对构型

  摘要：

  已经阐明了1-烷氧基异恶唑烷-3，3-二羧酸酯（1）的酰胺化的反式立体特异性。单酯4的碱性水解产生了盐6，其在以S（-）和R -（+）-苯基乙基铵盐的形式进行离子交换后被完全分离成对映体盐（+10和-10）。这些盐的酯化和酰胺化得到仅含有氮不对称中心的对映体2 S -（+12）和2 R -（-12）。产物的光学纯度是基于其具有位移试剂的NMR光谱确定的。通过X射线分析检测到分子和晶体结构以及+10的绝对构型。

  DOI：

  10.1016/s0040-4020(01)99484-0

文献信息

• Photochemical Strategies Enable the Synthesis of Tunable Azetidine-Based Energetic Materials
  作者：Katie A. Rykaczewski、Marc R. Becker、Manasi J. Anantpur、Rosario C. Sausa、Eric C. Johnson、Joshua A. Orlicki、Eric J. Bukowski、Jesse J. Sabatini、Corinna S. Schindler

  DOI：10.1021/jacs.2c08191

  日期：2022.10.19

  Despite their favorable properties, azetidines are often overlooked as lead compounds across multiple industries. This is often attributed to the challenging synthesis of densely functionalized azetidines in an efficient manner. In this work, we report the scalable synthesis and characterization of seven azetidines with varying regio- and stereochemistry and their application as novel azetidine-based

  尽管具有良好的特性，但氮杂环丁烷在多个行业中作为先导化合物经常被忽视。这通常归因于以有效方式合成密集官能化氮杂环丁烷具有挑战性。在这项工作中，我们报告了七种具有不同区域和立体化学的氮杂环丁烷的可扩展合成和表征，以及它们作为新型氮杂环丁烷基高能材料的应用，这是通过可见光介导的aza Paternò-Büchi 反应实现的。这些新化合物的性能和物理性质的明显差异使其成为新型固体可熔铸炸药材料以及潜在的液体推进剂增塑剂的极好潜在候选者。这项工作突出了可见光氮杂的可扩展性和实用性Paternò-Büchi 反应，并展示了立体化学因素对氮杂环丁烷基能量学物理性质的影响。考虑到所提出的合成策略的多功能性和效率，我们预计这项工作将指导新的氮杂环丁烷基材料在能量学领域以及其他行业的开发。
• Drefahl,G.; Hoerhold,H.-H., Chemische Berichte, 1964, vol. 97, p. 159 - 164
  作者：Drefahl,G.、Hoerhold,H.-H.

  DOI：——

  日期：——
• Synthesis and Testing of Heterocyclic Analogs of Diaminopimelic Acid (DAP) as Inhibitors of DAP Dehydrogenase and DAP Epimerase
  作者：Shaun D. Abbott、Patricia Lane-Bell、Kanwar P. S. Sidhu、John C. Vederas

  DOI：10.1021/ja00094a004

  日期：1994.7

  Substrate analogues were synthesized and examined as inhibitors of diaminopimelic acid (DAP) dehydrogenase from Bacillus sphaericus and of DAP epimerase from Escherichia coli. These enzymes produce meso-DAP (3) (a precursor for L-lysine and for peptidoglycan) from L-tetrahydrodipicolinic acid (1) and LL-DAP (2), respectively. The epimerase was purified by an improved procedure and confirmed to require both carboxyl and both amino groups for substrate recognition using deuterium-exchange experiments with DAP isomers, L-lysine, D-lysine, L-alpha-aminopimelate, and racemic alpha-aminopimelate. An imidazole analogue of DAP, (2S)-2-amino-3-(4-carboxyimidazol-1-yl)propanoic acid (4), was synthesized by condensation of benzyl imidazole-4-carboxylate (8) with N-benzyloxycarbonyl(Cbz)-L-serine beta-lactone (9) (product structure confirmed by X-ray analysis) followed by hydrogenolytic deprotection. Two other analogues, (2S,5'R)-2-amino-3-(3-carboxy-2-isoxazolin-5-yl)propanoic acid (5) and its 5'S diastereomer 6, were prepared by condensation of methyl N-Cbz-L-allylglycinate (13) with methyl chlorooximidoacetate (14) followed by separation of isomers and deprotection with NaOH and Me(3)SiCl/NaI. Similar condensation of ethyl chlorooximidoacetate with ethylene and of 14 with ethyl acrylate generated isoxazolines, which were saponified to 2-isoxazoline-3-carboxylic acid (25) and 2-isoxazoline-3,5-dicarboxylic acid (26), respectively. None of the compounds show significant inhibition of DAP epimerase or DAP dehydrogenase with the exception of 6, which is a potent and specific inhibitor of DAP dehydrogenase. At pH 7.5 or 7.8, compound 6 shows competitive inhibition (K-i = 4.2 mu M) with tetrahydrodipicolinic acid (1) for the forward reaction and noncompetitive inhibition (K-i = 23 mu M) with meso-DAP (3) for the reverse process. Preliminary tests for antimicrobial activity demonstrate that 6 inhibits the growth of B. sphaericus, which relies exclusively on DAP dehydrogenase to produce 3.
• Tartakovskii,V.A. et al., Journal of Organic Chemistry USSR (English Translation), 1968, vol. 4, p. 232 - 235
  作者：Tartakovskii,V.A. et al.

  DOI：——

  日期：——
• Intramolecular, Visible-Light-Mediated Aza Paternò-Büchi Reactions of Unactivated Alkenes
  作者：Dominique E. Blackmun、Stephen A. Chamness、Corinna S. Schindler

  DOI：10.1021/acs.orglett.2c01008

  日期：2022.4.29

表征谱图