methyl N-[1-(2-phenylmethoxyphenyl)-3-trimethylsilylprop-2-ynyl]-N-prop-2-enylcarbamate | 856438-48-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: methyl N-[1-(2-phenylmethoxyphenyl)-3-trimethylsilylprop-2-ynyl]-N-prop-2-enylcarbamate
• CAS: 856438-48-7
• 化学式: C₂₄H₂₉NO₃Si
• 分子量: 407.585
• InChiKey: VQWQZHHZGJLPCB-UHFFFAOYSA-N

物化性质

• 沸点：
  496.8±45.0 °C(Predicted)
• 密度：
  1.069±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.44
• 重原子数：
  29
• 可旋转键数：
  9
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  38.8
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  methyl N-[1-(2-phenylmethoxyphenyl)-3-trimethylsilylprop-2-ynyl]-N-prop-2-enylcarbamate 在 Pd-BaSO₄ 喹啉 、 sodium hydroxide 、 氨 、 氢气 、 sodium 、 potassium carbonate 、 pyridinium hydrobromide perbromide 、 2,3-二氯-5,6-二氰基-1,4-苯醌 作用下， 以 四氢呋喃 、 甲醇 、 乙醚 、 乙醇 、 乙酸乙酯 、 甲苯 为溶剂， 反应 122.41h， 生成 2,3,4-tribromo-5-(3,5-dibromo-2-methoxyphenyl)-1H-pyrrole
  参考文献：
  名称：

  A Re(V)-Catalyzed C−N Bond-Forming Route to Human Lipoxygenase Inhibitors

  摘要：

  A regioselective synthesis of propargylamines by the coupling of propargyl alcohols with tosylamines and carbamates catalyzed by an air and moisture-tolerant rhenium-oxo complex is described. The ability to couple functionalized components allows for convergent approaches to nitrogen-containing heterocyclic compounds such as the marine antibiotic pentabromopseudilin. These compounds were assayed against human lipoxygenase and found to be both potent and selective.

  DOI：

  10.1021/ol050897a
• 作为产物：
  描述：

  1-(2-benzyloxyphenyl)-3-(trimethylsilyl)prop-2-yn-1-ol 、 methyl allylcarbamate 在 (dppm)ReOCl₃ ammonium hexafluorophosphate 作用下， 以 乙腈 为溶剂， 反应 4.0h， 以99%的产率得到methyl N-[1-(2-phenylmethoxyphenyl)-3-trimethylsilylprop-2-ynyl]-N-prop-2-enylcarbamate
  参考文献：
  名称：

  A Re(V)-Catalyzed C−N Bond-Forming Route to Human Lipoxygenase Inhibitors

  摘要：

  A regioselective synthesis of propargylamines by the coupling of propargyl alcohols with tosylamines and carbamates catalyzed by an air and moisture-tolerant rhenium-oxo complex is described. The ability to couple functionalized components allows for convergent approaches to nitrogen-containing heterocyclic compounds such as the marine antibiotic pentabromopseudilin. These compounds were assayed against human lipoxygenase and found to be both potent and selective.

  DOI：

  10.1021/ol050897a

文献信息

• A Re(V)-Catalyzed C−N Bond-Forming Route to Human Lipoxygenase Inhibitors
  作者：Rachana V. Ohri、Alexander T. Radosevich、K. James Hrovat、Christine Musich、David Huang、Theodore R. Holman、F. Dean Toste

  DOI：10.1021/ol050897a

  日期：2005.6.1

  A regioselective synthesis of propargylamines by the coupling of propargyl alcohols with tosylamines and carbamates catalyzed by an air and moisture-tolerant rhenium-oxo complex is described. The ability to couple functionalized components allows for convergent approaches to nitrogen-containing heterocyclic compounds such as the marine antibiotic pentabromopseudilin. These compounds were assayed against human lipoxygenase and found to be both potent and selective.