2-Deutero-4-phenyl-oxazol | 54020-54-1

• 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-Deutero-4-phenyl-oxazol
• 英文别名: 2-deuterio-4-phenyl-oxazole；2-deuterio-4-phenyl-1,3-oxazole
• CAS: 54020-54-1
• 化学式: C₉H₇NO
• 分子量: 146.153
• InChiKey: NTFMLYSGIKHECT-WHRKIXHSSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.34
• 重原子数：
  11.0
• 可旋转键数：
  1.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  26.03
• 氢给体数：
  0.0
• 氢受体数：
  2.0

反应信息

• 作为产物：
  描述：

  4-苯基恶唑 在 正丁基锂 、 重水 作用下， 生成 2-Deutero-4-phenyl-oxazol
  参考文献：
  名称：

  Substituted oxazoles: syntheses via lithio intermediates

  摘要：

  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.

  DOI：

  10.1021/jo00009a025

文献信息

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

  DOI：——

  日期：——