Ethyl 4-(2-hydroxyethyl)-5-methyl-1,2-oxazole-3-carboxylate | 216962-32-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: Ethyl 4-(2-hydroxyethyl)-5-methyl-1,2-oxazole-3-carboxylate
• 英文别名: ethyl 4-(2-hydroxyethyl)-5-methyl-1,2-oxazole-3-carboxylate
• CAS: 216962-32-2
• 化学式: C₉H₁₃NO₄
• 分子量: 199.207
• InChiKey: VXDFXYOWKRBKNW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.9
• 重原子数：
  14
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.56
• 拓扑面积：
  72.6
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  Ethyl 4-(2-hydroxyethyl)-5-methyl-1,2-oxazole-3-carboxylate 在 戴斯-马丁氧化剂 、 溴化铵 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 生成 Ethyl 4-(2-amino-2-cyanoethyl)-5-methyl-1,2-oxazole-3-carboxylate
  参考文献：
  名称：

  ACPA和新型AMPA类似物的直接合成

  摘要：

  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。

  DOI：

  10.1016/s0040-4039(01)01796-8
• 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 Ethyl 4-(2-hydroxyethyl)-5-methyl-1,2-oxazole-3-carboxylate
  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

• 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.
• 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。