2-[Acetoxy-(3-p-tolyl-isoxazol-5-yl)-methyl]-acrylic acid butyl ester | 537031-08-6

• 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: 2-[Acetoxy-(3-p-tolyl-isoxazol-5-yl)-methyl]-acrylic acid butyl ester
• CAS: 537031-08-6
• 化学式: C₂₀H₂₃NO₅
• 分子量: 357.406
• InChiKey: KJVKUEXKXQQVPP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.15
• 重原子数：
  26.0
• 可旋转键数：
  8.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.35
• 拓扑面积：
  78.63
• 氢给体数：
  0.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  2-[Acetoxy-(3-p-tolyl-isoxazol-5-yl)-methyl]-acrylic acid butyl ester 、 苯酚 在 三乙烯二胺 作用下， 以 四氢呋喃 、 水 为溶剂， 反应 0.25h， 以83%的产率得到2-[phenoxy-(3-(4-methylphenyl)isoxazol-5-yl)methyl]acrylic acid butyl ester
  参考文献：
  名称：

  The Baylis–Hillman chemistry in aqueous media: elucidation of mechanism for synthesis of ether side-product leads to an efficient approach to C–O bond formation

  摘要：

  The formation of an ether from the Baylis-Hillman (BH) adduct during the BH reaction of 5-isoxazolecarboxaldehydes is a common phenomenon if the reaction is allowed to proceed for longer periods. The amount of formation of such ethers depends on the acrylates used and is most significant for tert-butyl acrylates. A study of the plausible mechanism for the formation of these side-products led to reactions of acetates of BH adducts with phenol in aqueous media to yield the corresponding 3-phenoxy alk-2-enoates in good yields. The successful translation of solution phase methodology to solid phase for application towards combinatorial chemistry is discussed. (C) 2003 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(02)01561-2
• 作为产物：
  描述：

  3-(p-tolyl)isoxazole-5-carbaldehyde 在 吡啶 、 三乙烯二胺 作用下， 以 二氯甲烷 为溶剂， 反应 0.33h， 生成 2-[Acetoxy-(3-p-tolyl-isoxazol-5-yl)-methyl]-acrylic acid butyl ester
  参考文献：
  名称：

  The Baylis–Hillman chemistry in aqueous media: elucidation of mechanism for synthesis of ether side-product leads to an efficient approach to C–O bond formation

  摘要：

  The formation of an ether from the Baylis-Hillman (BH) adduct during the BH reaction of 5-isoxazolecarboxaldehydes is a common phenomenon if the reaction is allowed to proceed for longer periods. The amount of formation of such ethers depends on the acrylates used and is most significant for tert-butyl acrylates. A study of the plausible mechanism for the formation of these side-products led to reactions of acetates of BH adducts with phenol in aqueous media to yield the corresponding 3-phenoxy alk-2-enoates in good yields. The successful translation of solution phase methodology to solid phase for application towards combinatorial chemistry is discussed. (C) 2003 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(02)01561-2