1-(2-cyclopentylphenyl)ethanone oxime | 934520-50-0

• 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: 1-(2-cyclopentylphenyl)ethanone oxime
• CAS: 934520-50-0
• 化学式: C₁₃H₁₇NO
• 分子量: 203.284
• InChiKey: PRIFQNLPKDZWPA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.54
• 重原子数：
  15.0
• 可旋转键数：
  2.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.46
• 拓扑面积：
  32.59
• 氢给体数：
  1.0
• 氢受体数：
  2.0

反应信息

• 作为反应物：
  描述：

  1-(2-cyclopentylphenyl)ethanone oxime 在 乙酸酐 作用下， 以 N,N-二甲基乙酰胺 为溶剂， 反应 0.5h， 以68%的产率得到3'-methylspiro[cyclopentane-1,1'-iso-indole]
  参考文献：
  名称：

  Novel Intramolecular Reactivity of Oximes:  Synthesis of Cyclic and Spiro-Fused Imines

  摘要：

  Under conventional heat (135-145 degrees C) or microwave irradiation and 1 equiv of acetic anhydride, ortho-substituted aryl-oximes undergo a novel sp(3) C-H activated cyclization to produce the corresponding isoindoles, and aliphatic oximes afford the corresponding dihydropyrroles. The cyclization occurs with various substrates in good yield (46-82%) leading to unique spiro-fused and cyclic imines. An initial mechanistic investigation suggests the reaction occurs via a nitrenium or vinyl nitrene intermediate.

  DOI：

  10.1021/ol0630043
• 作为产物：
  描述：

  cyclopentylzinc bromide 在 (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride copper(l) iodide 、 盐酸羟胺 、 sodium acetate 作用下， 以 甲醇 、 N,N-二甲基乙酰胺 为溶剂， 生成 1-(2-cyclopentylphenyl)ethanone oxime
  参考文献：
  名称：

  Novel Intramolecular Reactivity of Oximes:  Synthesis of Cyclic and Spiro-Fused Imines

  摘要：

  Under conventional heat (135-145 degrees C) or microwave irradiation and 1 equiv of acetic anhydride, ortho-substituted aryl-oximes undergo a novel sp(3) C-H activated cyclization to produce the corresponding isoindoles, and aliphatic oximes afford the corresponding dihydropyrroles. The cyclization occurs with various substrates in good yield (46-82%) leading to unique spiro-fused and cyclic imines. An initial mechanistic investigation suggests the reaction occurs via a nitrenium or vinyl nitrene intermediate.

  DOI：

  10.1021/ol0630043