(E)-3-[5-(4-methylphenyl)-1,2-oxazol-3-yl]prop-2-enal

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: (E)-3-[5-(4-methylphenyl)-1,2-oxazol-3-yl]prop-2-enal
• 化学式: C₁₃H₁₁NO₂
• 分子量: 213.236
• InChiKey: COSQNUHLXXVNLU-NSCUHMNNSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.86
• 重原子数：
  16.0
• 可旋转键数：
  3.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.08
• 拓扑面积：
  43.1
• 氢给体数：
  0.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  (E)-3-[5-(4-methylphenyl)-1,2-oxazol-3-yl]prop-2-enal 、 (R)-2,5-二氢-3,6-二甲氧基-2-异丙基吡嗪 在 正丁基锂 、 二异丙氧基二氯化钛 作用下， 以 四氢呋喃 、 正己烷 、 甲苯 为溶剂， 反应 1.5h， 以9.8%的产率得到(1R,2E)-1-((2S,5R)-5-isopropyl-3,6-dimethoxy-2,5-dihydro-pyrazin-2-yl)-3-(5-p-tolyl-isoxazol-3-yl)-prop-2-en-1-ol
  参考文献：
  名称：

  Stereoselective synthesis of δ-heteroaryl substituted β-hydroxy-γ,δ-unsaturated α-amino acids

  摘要：

  Enantiomerically pure 6-heteroaryl substituted beta-hydroxy-gamma, delta-unsaturated alpha-amino acids were stereoselectively synthesized starting from (2R)-(+)-2,5-dihydro-3,6-dimethoxy-2-isopropylpyrazine (Schollkoffs reagent) and suitable beta-heteroaryl-alpha, beta-unsaturated aldehydes. The stereocontrolled addition gave a mixture of two diastereoisomers whose configurations were assigned on the basis of spectroscopic data and the accepted model for aldol condensation of the Schollkoffs reagent. Upon controlled hydrolysis the adducts were transformed into the corresponding methyl esters of 6-heteroaryl substituted beta-hydroxy-gamma,delta-unsaturated alpha-amino acids. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2006.09.023