5-Methyl-4-(2-oxo-ethyl)-isoxazole-3-carboxylic acid ethyl ester | 216962-33-3

• 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-Methyl-4-(2-oxo-ethyl)-isoxazole-3-carboxylic acid ethyl ester
• 英文别名: Ethyl 5-methyl-4-(2-oxoethyl)-1,2-oxazole-3-carboxylate
• CAS: 216962-33-3
• 化学式: C₉H₁₁NO₄
• 分子量: 197.191
• InChiKey: KTTOQUSIBYNWQU-UHFFFAOYSA-N

物化性质

• 沸点：
  361.1±42.0 °C(Predicted)
• 密度：
  1.186±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.7
• 重原子数：
  14
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.44
• 拓扑面积：
  69.4
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  5-Methyl-4-(2-oxo-ethyl)-isoxazole-3-carboxylic acid ethyl ester 在 zirconium(IV) tert-butoxide N-甲基咪唑 、 盐酸 、 3-bromo-1,1'-bi-2-naphthol 、 (S)-6-bromo-2,2'-dihydroxy-1,1'-binaphthyl 作用下， 以 二氯甲烷 为溶剂， 反应 21.0h， 生成
  参考文献：
  名称：

  Catalytic Asymmetric Synthesis of Glutamate Analogues

  摘要：

  Utilizing our lateral metalation coupled with Jacobsen's catalytic asymmetric amino nitrile synthesis, we have demonstrated the ability to synthesize isoxazole-containing amino acid glutamate analogues in high yield and high enantiomeric excesses. Chiral centers alpha or beta at the C-5 position do not detract from diastereoselectivity of the Jacobsen-Strecker reaction.

  DOI：

  10.1021/ol049619m
• 作为产物：
  描述：

  3-isoxazolecarboxylic acid 5-methyl-4-(2,5,5-trimethyl-1,3-dioxan-2-yl)-ethyl ester 在 lead(IV) acetate 、 dimethyl sulfide borane 、 三氟化硼乙醚 、 对甲苯磺酸 作用下， 以 四氢呋喃 、 丙酮 、 苯 为溶剂， 生成 5-Methyl-4-(2-oxo-ethyl)-isoxazole-3-carboxylic acid ethyl ester
  参考文献：
  名称：

  Lateral lithiation of ethyl 4-acetyl-5-methyl-3-isoxazolyl carboxylate with 5,5-dimethyl-1,3-dioxanyl as a directing group

  摘要：

  Lateral lithiation of ethyl 4-acetyl-5-methyl-3-isoxazolyl carboxylate, a functionalized isoxazole AMPA analog, occurs cleanly at the C-5 methyl group with 5,5-dimethyl-1,3-dioxanyl as a directing group. The 4-acetyl isoxazole derivatives were transformed selectively by a modified Willgerodt-Kindler reaction into the corresponding homologated methyl esters after deprotection. (C) 1998 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(98)01782-1

文献信息

• A new direct synthesis of ACPA and novel AMPA analogues
  作者：David J Burkhart、Brendan Twamley、Nicholas R Natale

  DOI：10.1016/s0040-4039(01)01796-8

  日期：2001.11

  A novel synthesis of the potent glutamate neurotransmitter agonist (RS)-2-amino-3-(3-carboxy-5-methyl-4-isoxazolyl) propionic acid (ACPA) provides access to numerous analogues as drug candidates for neurological disorders. The one-pot synthesis of an alpha amino phosphonate from aldehyde 4 was successful using ErCl3 as a catalyst. Molecular modeling of the new amino phosphonic acid with the (RS)-2

  强大的谷氨酸神经递质激动剂（RS）-2-氨基-3-（3-羧基-5-甲基-4-异恶唑基）丙酸（ACPA）的新型合成方法可提供多种类似物作为神经系统疾病的候选药物。使用ErCl 3作为催化剂，成功地从醛4一锅合成α-氨基膦酸酯。具有（RS）-2-氨基-3-（3-羟基-5-甲基-4-异恶唑基）丙酸（AMPA）受体晶体结构的新型氨基膦酸的分子模型表明，这应该是一种有效的受体结合剂。
• Substitution of the phosphonic acid and hydroxamic acid functionalities of the DXR inhibitor FR900098: An attempt to improve the activity against Mycobacterium tuberculosis
  作者：Mounir Andaloussi、Martin Lindh、Christofer Björkelid、Surisetti Suresh、Anna Wieckowska、Harini Iyer、Anders Karlén、Mats Larhed

  DOI：10.1016/j.bmcl.2011.07.005

  日期：2011.9

  Two series of FR900098/fosmidomycin analogs were synthesized and evaluated for MtDXR inhibition and Mycobacterium tuberculosis whole-cell activity. The design rationale of these compounds involved the exchange of either the phosphonic acid or the hydroxamic acid part for alternative acidic and metal-coordinating functionalities. The best inhibitors provided IC(50) values in the micromolar range, with a best value of 41 mu M. (C) 2011 Elsevier Ltd. All rights reserved.
• Catalytic Asymmetric Synthesis of Glutamate Analogues
  作者：David J. Burkhart、Andrew R. McKenzie、Jared K. Nelson、Katherine I. Myers、Xue Zhao、Kathy R. Magnusson、Nicholas R. Natale

  DOI：10.1021/ol049619m

  日期：2004.4.1

  Utilizing our lateral metalation coupled with Jacobsen's catalytic asymmetric amino nitrile synthesis, we have demonstrated the ability to synthesize isoxazole-containing amino acid glutamate analogues in high yield and high enantiomeric excesses. Chiral centers alpha or beta at the C-5 position do not detract from diastereoselectivity of the Jacobsen-Strecker reaction.
• Lateral lithiation of ethyl 4-acetyl-5-methyl-3-isoxazolyl carboxylate with 5,5-dimethyl-1,3-dioxanyl as a directing group
  作者：Peiwen Zhou、N.R. Natale

  DOI：10.1016/s0040-4039(98)01782-1

  日期：1998.11

  Lateral lithiation of ethyl 4-acetyl-5-methyl-3-isoxazolyl carboxylate, a functionalized isoxazole AMPA analog, occurs cleanly at the C-5 methyl group with 5,5-dimethyl-1,3-dioxanyl as a directing group. The 4-acetyl isoxazole derivatives were transformed selectively by a modified Willgerodt-Kindler reaction into the corresponding homologated methyl esters after deprotection. (C) 1998 Elsevier Science Ltd. All rights reserved.