2-[Hydroxy-[3-(4-methylphenyl)-1,2-oxazol-5-yl]methyl]cyclopent-2-en-1-one | 452914-42-0

• 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-[Hydroxy-[3-(4-methylphenyl)-1,2-oxazol-5-yl]methyl]cyclopent-2-en-1-one
• CAS: 452914-42-0
• 化学式: C₁₆H₁₅NO₃
• 分子量: 269.3
• InChiKey: HEEVZECJRCMKEJ-UHFFFAOYSA-N

物化性质

• 沸点：
  526.3±50.0 °C(Predicted)
• 密度：
  1.278±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  20
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  63.3
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2-[Hydroxy-[3-(4-methylphenyl)-1,2-oxazol-5-yl]methyl]cyclopent-2-en-1-one 在 盐酸 作用下， 以 二氯甲烷 为溶剂， 反应 24.0h， 生成 3-chloro-2-[[3-(4-methylphenyl)-1,2-oxazol-5-yl]methylidene]cyclopentan-1-one
  参考文献：
  名称：

  TiCl₄-Promoted Baylis−Hillman Reactions of Substituted 5-Isoxazolecarboxaldehydes with Cycloalkenones¹

  摘要：

  The Baylis-Hillman (BH) reaction of substituted 5-isoxazolecarboxaldehydes with cyclohexenone in the presence of TiCl4 invariably lead to the formation of hemiacetals beside the BH adducts. A similar reaction in the presence of DABCO, DBU, or 3-HQN yielded minor quantities of phenols in addition to the usual BH adducts. Similar to 5-isoxazolecarboxaldehydes, the TiCl4-mediated BH reaction of cyclohexenone with various benzaldehydes also furnishes hemiacetals in considerable yields. The reaction mechanism involving the formation of a-chloromethyl enone as an intermediate has been proposed. The synthesis of hemiacetals 5 and 14 from compound 4 in the presence of cyclohexenone and cyclopentenone, respectively, under acidic conditions indicates that enolization and aromatization of the cyclohexene ring are the key steps in the reaction mechanism.

  DOI：

  10.1021/jo020199t
• 作为产物：
  描述：

  2-环戊烯酮 、 3-(p-tolyl)isoxazole-5-carbaldehyde 在 四氯化钛 作用下， 以 二氯甲烷 为溶剂， 反应 1.0h， 以69%的产率得到2-[Hydroxy-[3-(4-methylphenyl)-1,2-oxazol-5-yl]methyl]cyclopent-2-en-1-one
  参考文献：
  名称：

  TiCl₄-Promoted Baylis−Hillman Reactions of Substituted 5-Isoxazolecarboxaldehydes with Cycloalkenones¹

  摘要：

  The Baylis-Hillman (BH) reaction of substituted 5-isoxazolecarboxaldehydes with cyclohexenone in the presence of TiCl4 invariably lead to the formation of hemiacetals beside the BH adducts. A similar reaction in the presence of DABCO, DBU, or 3-HQN yielded minor quantities of phenols in addition to the usual BH adducts. Similar to 5-isoxazolecarboxaldehydes, the TiCl4-mediated BH reaction of cyclohexenone with various benzaldehydes also furnishes hemiacetals in considerable yields. The reaction mechanism involving the formation of a-chloromethyl enone as an intermediate has been proposed. The synthesis of hemiacetals 5 and 14 from compound 4 in the presence of cyclohexenone and cyclopentenone, respectively, under acidic conditions indicates that enolization and aromatization of the cyclohexene ring are the key steps in the reaction mechanism.

  DOI：

  10.1021/jo020199t

文献信息

• Isoxazole-based derivatives from Baylis–Hillman chemistry: assessment of preliminary hypolipidemic activity
  作者：A Patra、S Batra、A.P Bhaduri、A Khanna、R Chander、M Dikshit

  DOI：10.1016/s0968-0896(03)00105-6

  日期：2003.5

  The synthesis of isoxazole-based derivatives utilizing Baylis-Hillman chemistry and results of their preliminary bioevaluation as hypolipidemic agents in triton model are described. (C) 2003 Elsevier Science Ltd. All rights reserved.
• TiCl₄-Promoted Baylis−Hillman Reactions of Substituted 5-Isoxazolecarboxaldehydes with Cycloalkenones¹
  作者：Arundhati Patra、Sanjay Batra、Bhawani S. Joshi、Raja Roy、Bijoy Kundu、Amiya P. Bhaduri

  DOI：10.1021/jo020199t

  日期：2002.8.1

  The Baylis-Hillman (BH) reaction of substituted 5-isoxazolecarboxaldehydes with cyclohexenone in the presence of TiCl4 invariably lead to the formation of hemiacetals beside the BH adducts. A similar reaction in the presence of DABCO, DBU, or 3-HQN yielded minor quantities of phenols in addition to the usual BH adducts. Similar to 5-isoxazolecarboxaldehydes, the TiCl4-mediated BH reaction of cyclohexenone with various benzaldehydes also furnishes hemiacetals in considerable yields. The reaction mechanism involving the formation of a-chloromethyl enone as an intermediate has been proposed. The synthesis of hemiacetals 5 and 14 from compound 4 in the presence of cyclohexenone and cyclopentenone, respectively, under acidic conditions indicates that enolization and aromatization of the cyclohexene ring are the key steps in the reaction mechanism.