3-(4-methoxyphenyl)-4,5-dihydroisoxazole-5-carboxylic acid methyl ester | 140946-63-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: 3-(4-methoxyphenyl)-4,5-dihydroisoxazole-5-carboxylic acid methyl ester
• 英文别名: methyl 3-(4-methoxyphenyl)-4,5-dihydroisoxazole-5-carboxylate；Methyl 3-(4-methoxyphenyl)-4,5-dihydro-1,2-oxazole-5-carboxylate
• CAS: 140946-63-0
• 化学式: C₁₂H₁₃NO₄
• 分子量: 235.24
• InChiKey: OQNOEZWSWXHCHA-UHFFFAOYSA-N

物化性质

• 熔点：
  75-77 °C
• 沸点：
  334.0±52.0 °C(Predicted)
• 密度：
  1.24±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  17
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  57.1
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  3-(4-methoxyphenyl)-4,5-dihydroisoxazole-5-carboxylic acid methyl ester 在 sodium hydroxide 、 氯化亚砜 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 为溶剂， 反应 2.0h， 生成
  参考文献：
  名称：

  Inhibition of the Antibacterial Target UDP-(3-O-acyl)-N-acetylglucosamine Deacetylase (LpxC):  Isoxazoline Zinc Amidase Inhibitors Bearing Diverse Metal Binding Groups

  摘要：

  UDP-3-O-[R-3-hydroxymyristoyl]-GlcNAc deacetylase (LpxC) is a zinc amidase that catalyzes the second step of lipid A biosynthesis in Gram negative bacteria. Known inhibitors of this enzyme are oxazolines incorporating a hydroxamic acid at the 4-position, which is believed to coordinate to the single essential zinc ion. A new structural class of inhibitors was designed to incorporate a more stable and more synthetically. versatile isoxazoline core. The synthetic versatility of the isoxazoline allowed for a broad study of metal binding. groups. Nine of 17 isoxazolines, each incorporating a different potential metal binding functional group, were found to exhibit enzyme inhibitory activity, including one that is more active than the corresponding hydroxamic acid. Additionally, a designed affinity label inhibits LpxC in a time-dependent manner.

  DOI：

  10.1021/jm020183v
• 作为产物：
  描述：

  对甲氧基苯甲醛肟 在 吡啶 、 三氯异氰尿酸 作用下， 以 二氯甲烷 为溶剂， 反应 48.0h， 生成 3-(4-methoxyphenyl)-4,5-dihydroisoxazole-5-carboxylic acid methyl ester
  参考文献：
  名称：

  4,5-二氢异恶唑对根结线虫的毒性及其作用方式的计算机模拟研究。

  摘要：

  目前的工作试图为新型杀线虫剂的开发做出贡献。苯甲醛最初被转化为腈，与丙烯酸甲酯进行1,3-偶极环加成反应生成4,5-二氢异恶唑。在体外测试中，3-苯基-4,5-二氢异恶唑-5-羧酸甲酯（1）和3-（4-氯苯基）-4,5-二氢异恶唑-5-羧酸甲酯（4）增加了Meloidogyne exigua的死亡率。和Meloidogyne incognita第二阶段的少年（J2）。化合物1和4分别呈现出必要的浓度398和501μgmL-1，以杀死50％的M. incognita J2（LC50值），而呋喃丹的浓度（阳性对照）为168μgmL-1。在体内测试中，化合物1和4分别使番茄根中的隐孢子虫胆虫数量减少70％和40％，鸡蛋数量减少89％和44％。使用计算机方法，我们显示化合物1和4通过与线虫烟碱型乙酰胆碱受体激动剂结合域的变构结合位点结合，对线虫有毒。这些结果为进一步研究开发新型商业杀线虫剂提供了可能性。

  DOI：

  10.1021/acs.jafc.9b07839

文献信息

• Hypervalent Iodine–Catalyzed Cycloaddition of Nitrile Oxides to Alkenes
  作者：Changbin Xiang、Tingting Li、Jie Yan

  DOI：10.1080/00397911.2013.834364

  日期：2014.3.4

  convenient method for preparation of isoxazolines was developed by a catalytic cycloaddition of nitrile oxides generated in situ from aldoximes to alkenes in the presence of a catalytic amount of iodobenzene. In this protocol, iodobenzene was first oxidized into the hypervalent iodine intermediate by m-chloroperbenzoic acid, which then transformed aldoximes into nitrile oxides, and a 1,3-dipolar cycloaddition

  摘要 通过在催化量的碘苯存在下，将醛肟原位生成的腈氧化物催化环加成反应，开发了一种新的、方便的制备异恶唑啉的方法。在该协议中，碘苯首先被间氯过苯甲酸氧化成高价碘中间体，然后将醛肟转化为腈氧化物，以及腈氧化物与烯烃的 1,3-偶极环加成反应，以中等至良好的收率提供异恶唑啉。[本文提供补充材料。访问出版商的 Synthetic Communications® 在线版，获取以下免费补充资源：完整的实验和光谱细节。] 图形摘要
• KF/Al₂O₃: Solid-Supported Reagent Used in 1,3-Dipolar Cycloaddition Reaction of Nitrile Oxide
  作者：Monalisa Boruah、Dilip Konwar

  DOI：10.1080/00397911.2011.558665

  日期：2012.11.15

  Abstract The stereoselective synthesis of 2-isoxazolidine through 1,3-dipolar cycloaddition reaction of nitrile oxide, which is in situ generation from aldoxime in the presence of N-bromosuccinamide and solid-supported reagent KF/Al2O3 at room temperature, is reported. KF/Al2O3 is sufficiently basic such that it can replace organic bases such as Et3N used in typical procedures and it catalyses the

  摘要 报道了在室温下，在 N-溴代琥珀酰胺和固载试剂 KF/Al2O3 存在下，由醛肟原位生成腈氧化物的 1,3-偶极环加成反应立体选择性合成 2-异恶唑烷。KF/Al2O3 具有足够的碱性，因此它可以替代典型程序中使用的有机碱，例如 Et3N，并且它催化反应以提高反应速率。图形概要
• GRANT, R. D.;PINHEY, J. T.;RIZZARDO, E., AUSTRAL. J. CHEM., 1984, 37, N 6, 1217-1229
  作者：GRANT, R. D.、PINHEY, J. T.、RIZZARDO, E.

  DOI：——

  日期：——
• Toxicities of 4,5-Dihydroisoxazoles Against Root-Knot Nematodes and in Silico Studies of Their Modes of Action
  作者：Rodrigo M. Fráguas、Viviane A. Costa、Willian C. Terra、Alcino P. Aguiar、Samuel J. Martins、Vicente P. Campos、Denilson F. Oliveira

  DOI：10.1021/acs.jafc.9b07839

  日期：2020.1.15

  to contribute to the development of new nematicides. Benzaldehydes were initially converted to nitrile oxides that underwent 1,3-dipolar cycloaddition reactions with methyl acrylate to generate 4,5-dihydroisoxazoles. In in vitro tests, methyl 3-phenyl-4,5-dihydroisoxazole-5-carboxylate (1) and methyl 3-(4-chlorophenyl)-4,5-dihydroisoxazole-5-carboxylate (4) increased the mortality of Meloidogyne exigua

  目前的工作试图为新型杀线虫剂的开发做出贡献。苯甲醛最初被转化为腈，与丙烯酸甲酯进行1,3-偶极环加成反应生成4,5-二氢异恶唑。在体外测试中，3-苯基-4,5-二氢异恶唑-5-羧酸甲酯（1）和3-（4-氯苯基）-4,5-二氢异恶唑-5-羧酸甲酯（4）增加了Meloidogyne exigua的死亡率。和Meloidogyne incognita第二阶段的少年（J2）。化合物1和4分别呈现出必要的浓度398和501μgmL-1，以杀死50％的M. incognita J2（LC50值），而呋喃丹的浓度（阳性对照）为168μgmL-1。在体内测试中，化合物1和4分别使番茄根中的隐孢子虫胆虫数量减少70％和40％，鸡蛋数量减少89％和44％。使用计算机方法，我们显示化合物1和4通过与线虫烟碱型乙酰胆碱受体激动剂结合域的变构结合位点结合，对线虫有毒。这些结果为进一步研究开发新型商业杀线虫剂提供了可能性。
• Inhibition of the Antibacterial Target UDP-(3-<i>O</i>-acyl)-<i>N</i>-acetylglucosamine Deacetylase (LpxC):  Isoxazoline Zinc Amidase Inhibitors Bearing Diverse Metal Binding Groups
  作者：Michael C. Pirrung、L. Nathan Tumey、Christian R. H. Raetz、Jane E. Jackman、Karnem Snehalatha、Amanda L. McClerren、Carol A. Fierke、Stephanie L. Gantt、Kristin M. Rusche

  DOI：10.1021/jm020183v

  日期：2002.9.1

  UDP-3-O-[R-3-hydroxymyristoyl]-GlcNAc deacetylase (LpxC) is a zinc amidase that catalyzes the second step of lipid A biosynthesis in Gram negative bacteria. Known inhibitors of this enzyme are oxazolines incorporating a hydroxamic acid at the 4-position, which is believed to coordinate to the single essential zinc ion. A new structural class of inhibitors was designed to incorporate a more stable and more synthetically. versatile isoxazoline core. The synthetic versatility of the isoxazoline allowed for a broad study of metal binding. groups. Nine of 17 isoxazolines, each incorporating a different potential metal binding functional group, were found to exhibit enzyme inhibitory activity, including one that is more active than the corresponding hydroxamic acid. Additionally, a designed affinity label inhibits LpxC in a time-dependent manner.