2a-hydroxy-2a,3,3a,4,5,6-hexahydro-2H,8H-oxeto[3,2-d]pyrrolo[1,2-a]azepin-8-one

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吖庚因类
• 英文名称: 2a-hydroxy-2a,3,3a,4,5,6-hexahydro-2H,8H-oxeto[3,2-d]pyrrolo[1,2-a]azepin-8-one
• 英文别名: (1R,3R)-3-hydroxy-5-oxa-9-azatricyclo[7.3.0.03,6]dodec-6-en-8-one
• 化学式: C₁₀H₁₃NO₃
• 分子量: 195.218
• InChiKey: LROLHVNAEXJZQC-GMSGAONNSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.6
• 重原子数：
  14
• 可旋转键数：
  0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.7
• 拓扑面积：
  49.8
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2a-hydroxy-2a,3,3a,4,5,6-hexahydro-2H,8H-oxeto[3,2-d]pyrrolo[1,2-a]azepin-8-one 在 platinum on activated charcoal sodium periodate 、 氢气 作用下， 以 乙醇 、 水 为溶剂， 反应 54.0h， 生成 hexahydropyrrolo[1,2-a]azepine-5,8-dione
  参考文献：
  名称：

  Rapid Access to Azepine-Fused Oxetanols from Alkoxy-Substituted Maleimides

  摘要：

  UV irradiation of alkoxy-substituted N-alkenylmaleimides induces a sequence involving a [5 + 2] cycloaddition followed by a Norrish-Yang cyclization. The resulting highly strained alkylidene oxetanol-fused azepines are formed in good yield and with high diastereoselectivities.

  DOI：

  10.1021/ol049645k
• 作为产物：
  描述：

  3-methoxy-1-(4-pentenyl)-1H-pyrrole-2,5-dione 以 乙腈 为溶剂， 反应 0.67h， 以14%的产率得到6-methoxy-2,3,9,9a-tetrahydro-1H-pyrrolo[1,2-a]azepine-5,8-dione
  参考文献：
  名称：

  Rapid Access to Azepine-Fused Oxetanols from Alkoxy-Substituted Maleimides

  摘要：

  UV irradiation of alkoxy-substituted N-alkenylmaleimides induces a sequence involving a [5 + 2] cycloaddition followed by a Norrish-Yang cyclization. The resulting highly strained alkylidene oxetanol-fused azepines are formed in good yield and with high diastereoselectivities.

  DOI：

  10.1021/ol049645k

文献信息

• Acid-Catalyzed Rearrangement of Fused Alkylideneoxetanols
  作者：Paul J. Hickford、James R. Baker、Ian Bruce、Kevin I. Booker-Milburn

  DOI：10.1021/ol701625q

  日期：2007.11.1

  Complex aza-fuzed tricyclic lactones are obtained in a two-step photochemical cycloaddition/acid-catalyzed rearrangement of simple alkoxy maleimide derivatives. The sequence involves a complex acid-catalyzed skeletal rearrangement of the intermediate alkylideneoxetanols.

  在简单的烷氧基马来酰亚胺衍生物的两步光化学环加成/酸催化的重排中获得了复杂的氮杂稠合的三环内酯。该序列涉及中间亚烷基氧杂环丁烷醇的复杂的酸催化的骨架重排。
• Rapid Access to Azepine-Fused Oxetanols from Alkoxy-Substituted Maleimides
  作者：Kevin I. Booker-Milburn、James R. Baker、Ian Bruce

  DOI：10.1021/ol049645k

  日期：2004.4.1

  UV irradiation of alkoxy-substituted N-alkenylmaleimides induces a sequence involving a [5 + 2] cycloaddition followed by a Norrish-Yang cyclization. The resulting highly strained alkylidene oxetanol-fused azepines are formed in good yield and with high diastereoselectivities.