2-ethoxy-4,5-dimethyloxazole | 129487-21-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 2-ethoxy-4,5-dimethyloxazole
• 英文别名: 2-Ethoxy-4,5-dimethyl-1,3-oxazole
• CAS: 129487-21-4
• 化学式: C₇H₁₁NO₂
• 分子量: 141.17
• InChiKey: NGLJFOIPZYTZDU-UHFFFAOYSA-N

物化性质

• 沸点：
  191.0±43.0 °C(Predicted)
• 密度：
  1.019±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  10
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.57
• 拓扑面积：
  35.3
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  2--3-<(ethoxycarbonyl)oxy>-2-butene 反应 48.0h， 以55%的产率得到2-ethoxy-4,5-dimethyloxazole
  参考文献：
  名称：

  Synthesis of oxazoles from O-trimethylsilyl acyltrimethylsilane cyanohydrins

  摘要：

  Sequential addition of organolithium reagents and acyl chlorides (or anhydrides) to O-trimethylsilyl acyltrimethylsilane cyanohydrins affords beta-(acyloxy)-N,N-bis(trimethylsilyl) enamines which cyclize to substituted oxazoles under thermolysis or treatment with trimethylsilyl trifluoromethanesulfonate. Oxazoles were prepared containing alkyl and phenyl substituents at C-5, alkyl, alkenyl, and phenyl substituents at C-4, and alkyl, alkenyl, phenyl, and functionalized substituents at C-2.

  DOI：

  10.1021/jo00038a020

文献信息

• Oxazoles from β-acyloxy-n,n-bis(trimethylsilyl)enamines
  作者：Robert F. Cunico、Chia P. Kuan

  DOI：10.1016/s0040-4039(00)88885-1

  日期：1990.1
• Substituted oxazoles: syntheses via lithio intermediates
  作者：Scott E. Whitney、Bruce Rickborn

  DOI：10.1021/jo00009a025

  日期：1991.4

  Reactions of 2-alpha-, 2-, 4-, and 5-lithiooxazoles are used to prepare various substituted derivatives. Previously unrecognized time dependence for the reaction of a 2-lithiooxazole with benzaldehyde is described, and a rationale for this behavior is offered. Competitive reactions occur when the readily available 2,5-diphenyloxazole is treated with n-butyllithium. Deprotonation of the ortho position of the 2-phenyl group and addition of n-butyl to the 2-position of the oxazole compete with the desired 4-lithiation. The use of sec-butyllithium/catalytic lithium tetramethylpiperidide allows preferential formation of 4-lithio-25-diphenyloxazole. This intermediate has been converted to the 4-bromo, -methyl, -hydroxybenzyl, -benzoyl, and -trialkylsilyl derivatives. Lithiation of 2,4-diphenyloxazole and subsequent trimethylsilylation occur readily at the 5-position. Deprotonation of 2-alkyloxazoles occurs at the alpha-carbon in preference to ring sites. Further reaction of an alpha-phenyl-2-oxazolemethanol methoxymethyl ether with base and acetyl chloride leads to an acyloin derivative. Chromic acid oxidation is used to prepare both 2- and 4-benzoyloxazoles. The formation of a 2-ethoxyoxazole from the 2-oxazolone vis Meerwein salt chemistry is described.
• CUNICO, ROBERT F.;KUAN, CHIA P., TETRAHEDRON LETT., 31,(1990) N4, C. 1945-1948
  作者：CUNICO, ROBERT F.、KUAN, CHIA P.

  DOI：——

  日期：——
• WHITNEY, SCOTT E.;RICKBORN, BRUCE, J. ORG. CHEM., 56,(1991) N, C. 3058-3063
  作者：WHITNEY, SCOTT E.、RICKBORN, BRUCE

  DOI：——

  日期：——