3-but-3-enyloxy-cyclopent-2-enone

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 乙烯酯类
• 英文名称: 3-but-3-enyloxy-cyclopent-2-enone
• 英文别名: 3-But-3-enoxycyclopent-2-en-1-one；3-but-3-enoxycyclopent-2-en-1-one
• 化学式: C₉H₁₂O₂
• 分子量: 152.193
• InChiKey: GAHRJZBPEVDQEN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.3
• 重原子数：
  11
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.44
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  3-but-3-enyloxy-cyclopent-2-enone 以 乙腈 为溶剂， 反应 1.5h， 以13%的产率得到(1RS,5RS,7SR)-2-oxa-tricyclo[5.3.0.0(1,5)]decan-8-one
  参考文献：
  名称：

  In situ Reduction in Photocycloadditions: A Method to Prevent Secondary Photoreactions

  摘要：

  Secondary photoreactions are a common cause for the low yields often observed in photochemical reactions, preventing their widespread deployment in synthesis. In situ reductions which remove the chromophore from the product as it is formed provide a convenient method to prevent these secondary photoreactions.

  DOI：

  10.1021/ol8026494
• 作为产物：
  描述：

  1,3-环戊二酮 、 3-丁烯-1-醇 在 对甲苯磺酸 作用下， 以 甲苯 为溶剂， 以85%的产率得到3-but-3-enyloxy-cyclopent-2-enone
  参考文献：
  名称：

  Reactivity of tris(trimethylsilyl)silyl radical with β-alkenyloxyenones

  摘要：

  The addition of tris(trimethylsilyl)silyl radical on beta-alkenyloxyenones generates an alkyl radical that can add onto the enone moiety. The tetrahydrofuranyl system so-obtained can undergo beta-elimination leading to 3-alkylcycloalken-2-ones.

  DOI：

  10.1016/0040-4039(95)01463-r

文献信息

• Reactivity of tris(trimethylsilyl)silyl radical with β-alkenyloxyenones
  作者：Janine Cossy、Laurent Sallé

  DOI：10.1016/0040-4039(95)01463-r

  日期：1995.10

  The addition of tris(trimethylsilyl)silyl radical on beta-alkenyloxyenones generates an alkyl radical that can add onto the enone moiety. The tetrahydrofuranyl system so-obtained can undergo beta-elimination leading to 3-alkylcycloalken-2-ones.
• In situ Reduction in Photocycloadditions: A Method to Prevent Secondary Photoreactions
  作者：Lauren M. Tedaldi、James R. Baker

  DOI：10.1021/ol8026494

  日期：2009.2.19

  Secondary photoreactions are a common cause for the low yields often observed in photochemical reactions, preventing their widespread deployment in synthesis. In situ reductions which remove the chromophore from the product as it is formed provide a convenient method to prevent these secondary photoreactions.