噁唑,2,5-二苯基-4-(三乙基甲硅烷基)- | 133229-65-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 中文名称: 噁唑,2,5-二苯基-4-(三乙基甲硅烷基)-
• 英文名称: 4-(triethylsilyl)-2,5-diphenyloxazole
• 英文别名: (2,5-Diphenyl-1,3-oxazol-4-yl)-triethylsilane
• CAS: 133229-65-9
• 化学式: C₂₁H₂₅NOSi
• 分子量: 335.521
• InChiKey: RWRMCLGVJCWFRR-UHFFFAOYSA-N

物化性质

• 沸点：
  459.7±47.0 °C(Predicted)
• 密度：
  1.05±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.72
• 重原子数：
  24
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  26
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  2,5-二苯基恶唑 、 正丁基锂 、 三乙基氯硅烷 以71%的产率得到
  参考文献：
  名称：

  WHITNEY, SCOTT E.;RICKBORN, BRUCE, J. ORG. CHEM., 56,(1991) N, C. 3058-3063

  摘要：

  DOI：

文献信息

• 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.