1-{5,6-difluoro-2-[(3-methylbut-2-en-1-yl)oxy] phenyl}-3-N-Boc-methylaminoprop-2-yn-ol | 1412443-34-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: 1-{5,6-difluoro-2-[(3-methylbut-2-en-1-yl)oxy] phenyl}-3-N-Boc-methylaminoprop-2-yn-ol
• 英文别名: tert-butyl N-[4-[2,3-difluoro-6-(3-methylbut-2-enoxy)phenyl]-4-hydroxybut-2-ynyl]carbamate
• CAS: 1412443-34-5
• 化学式: C₂₀H₂₅F₂NO₄
• 分子量: 381.42
• InChiKey: JMSQUNKRQFQQPN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  27
• 可旋转键数：
  7
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.45
• 拓扑面积：
  67.8
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  1-{5,6-difluoro-2-[(3-methylbut-2-en-1-yl)oxy] phenyl}-3-N-Boc-methylaminoprop-2-yn-ol 在 硝酸铈(3+)铵 、 三氟化硼乙醚 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 0.75h， 生成 3-(1-fluoro-1-methylethyl)-5,6-difluoro-4-(N-Boc-methylaminoethynyl)chromane
  参考文献：
  名称：

  A highly diastereoselective series of Nicholas cyclisation reactions of N-Boc-protected propargylamines

  摘要：

  The reaction of N-Boc-protected propargylamine with salicylaldehyde derivatives and their subsequent Nicholas cyclisation reaction to provide a range of novel benzopyrans is reported. The cyclisation reactions proceeded with excellent levels of diastereoselectivity to afford compounds with cis-relative stereochemistry. As far as we are able to ascertain these are the first reported examples of Nicholas cyclisation reactions of propargyl alcohols that bear a terminal alkynyl N-protected amino motif. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2012.08.087
• 作为产物：
  描述：

  1-溴-3-甲基-2-丁烯 在 potassium carbonate 、 potassium iodide 、 lithium diisopropyl amide 作用下， 以 四氢呋喃 、 正庚烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 4.0h， 生成 1-{5,6-difluoro-2-[(3-methylbut-2-en-1-yl)oxy] phenyl}-3-N-Boc-methylaminoprop-2-yn-ol
  参考文献：
  名称：

  A highly diastereoselective series of Nicholas cyclisation reactions of N-Boc-protected propargylamines

  摘要：

  The reaction of N-Boc-protected propargylamine with salicylaldehyde derivatives and their subsequent Nicholas cyclisation reaction to provide a range of novel benzopyrans is reported. The cyclisation reactions proceeded with excellent levels of diastereoselectivity to afford compounds with cis-relative stereochemistry. As far as we are able to ascertain these are the first reported examples of Nicholas cyclisation reactions of propargyl alcohols that bear a terminal alkynyl N-protected amino motif. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2012.08.087

文献信息

• A highly diastereoselective series of Nicholas cyclisation reactions of N-Boc-protected propargylamines
  作者：Peter Brawn、Elizabeth Tyrrell、Mark Carew、Kibur Hunie Tesfa、Iain Greenwood

  DOI：10.1016/j.tet.2012.08.087

  日期：2012.12

  The reaction of N-Boc-protected propargylamine with salicylaldehyde derivatives and their subsequent Nicholas cyclisation reaction to provide a range of novel benzopyrans is reported. The cyclisation reactions proceeded with excellent levels of diastereoselectivity to afford compounds with cis-relative stereochemistry. As far as we are able to ascertain these are the first reported examples of Nicholas cyclisation reactions of propargyl alcohols that bear a terminal alkynyl N-protected amino motif. (C) 2012 Elsevier Ltd. All rights reserved.