4-cyclohexenyl-1H-indol-5-ol | 1413811-03-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吲哚及其衍生物
• 英文名称: 4-cyclohexenyl-1H-indol-5-ol
• 英文别名: 4-(cyclohexen-1-yl)-1H-indol-5-ol
• CAS: 1413811-03-6
• 化学式: C₁₄H₁₅NO
• 分子量: 213.279
• InChiKey: NDWGDHWHEPCPKQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  16
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  36
• 氢给体数：
  2
• 氢受体数：
  1

反应信息

• 作为产物：
  描述：

  tert-butyl 4-cyclohexenyl-2-hydroxybut-3-ynyl(furan-2-yl)-carbamate 以 1,2-二氯乙烷 为溶剂， 反应 0.5h， 以23%的产率得到4-cyclohexenyl-1H-indol-5-ol
  参考文献：
  名称：

  5-Hydroxyindoles by Intramolecular Alkynol–Furan Diels–Alder Cycloaddition

  摘要：

  A convergent approach provides a convenient access to synthetically and biologically useful 3,4-disubstituted 5-hydroxyindoles. The one-pot procedure uses microwave heating to initiate an intramolecular [4 + 2]-cycloaddition of an alkynol segment onto a furan followed by a fragmentation, aromatization, and N-Boc deprotection cascade. Yields range from 15 to 74%, with aromatic substituents providing better conversions. 4-Trimethylsilylated analogues undergo a 1,3-silatropic rearrangement to give the O-TMS ethers.

  DOI：

  10.1021/jo3022605

文献信息

• 5-Hydroxyindoles by Intramolecular Alkynol–Furan Diels–Alder Cycloaddition
  作者：Matthew LaPorte、Ki Bum Hong、Jie Xu、Peter Wipf

  DOI：10.1021/jo3022605

  日期：2013.1.4

  A convergent approach provides a convenient access to synthetically and biologically useful 3,4-disubstituted 5-hydroxyindoles. The one-pot procedure uses microwave heating to initiate an intramolecular [4 + 2]-cycloaddition of an alkynol segment onto a furan followed by a fragmentation, aromatization, and N-Boc deprotection cascade. Yields range from 15 to 74%, with aromatic substituents providing better conversions. 4-Trimethylsilylated analogues undergo a 1,3-silatropic rearrangement to give the O-TMS ethers.