tert-butyl furan-2-yl(2-hydroxy-2,4-diphenylbut-3-ynyl)carbamate | 1413809-69-4

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 直链 1,3-二芳基丙烷
• 英文名称: tert-butyl furan-2-yl(2-hydroxy-2,4-diphenylbut-3-ynyl)carbamate
• 英文别名: tert-butyl N-(furan-2-yl)-N-(2-hydroxy-2,4-diphenylbut-3-ynyl)carbamate
• CAS: 1413809-69-4
• 化学式: C₂₅H₂₅NO₄
• 分子量: 403.478
• InChiKey: NDMWEYLYSIPLSR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.8
• 重原子数：
  30
• 可旋转键数：
  8
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.24
• 拓扑面积：
  62.9
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  tert-butyl furan-2-yl(2-hydroxy-2,4-diphenylbut-3-ynyl)carbamate 以 邻二氯苯 为溶剂， 反应 1.0h， 以74%的产率得到3,4-diphenyl-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
• 作为产物：
  描述：

  三丁基(碘甲基)锡烷 、 二苯基丙炔酮 、 N-[4-三氟甲基嘧啶-2-基]乙二胺 在 sodium hydride 、 正丁基锂 作用下， 以 N,N-二甲基甲酰胺 、 四氢呋喃 、 正己烷 为溶剂， 反应 1.34h， 以0.29 g的产率得到tert-butyl furan-2-yl(2-hydroxy-2,4-diphenylbut-3-ynyl)carbamate
  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.