1-[2-(tert-butyldimethylsiloxy)phenyl]-5-[1-(toluene-4-sulfonyl)-1,2,3,6-tetrahydropyridin-4-yl]-pent-3-yn-1-one | 827575-42-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 1-[2-(tert-butyldimethylsiloxy)phenyl]-5-[1-(toluene-4-sulfonyl)-1,2,3,6-tetrahydropyridin-4-yl]-pent-3-yn-1-one
• 英文别名: 1-[2-[tert-butyl(dimethyl)silyl]oxyphenyl]-5-[1-(4-methylphenyl)sulfonyl-3,4-dihydro-2H-pyridin-4-yl]pent-2-yn-1-one
• CAS: 827575-42-8
• 化学式: C₂₉H₃₇NO₄SSi
• 分子量: 523.769
• InChiKey: IWCNNZNFCZRKDK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.57
• 重原子数：
  36
• 可旋转键数：
  8
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.41
• 拓扑面积：
  72.1
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  1-[2-(tert-butyldimethylsiloxy)phenyl]-5-[1-(toluene-4-sulfonyl)-1,2,3,6-tetrahydropyridin-4-yl]-pent-3-yn-1-one 在 platinum(II) chloride 作用下， 以 甲苯 为溶剂， 反应 1.25h， 以63%的产率得到(2E)-1-[2-[tert-butyl(dimethyl)silyl]oxyphenyl]-2-[2-(4-methylphenyl)sulfonyl-4,4a,5,6-tetrahydro-3H-cyclopenta[c]pyridin-7-ylidene]ethanone
  参考文献：
  名称：

  Pt(II) or Ag(I) Salt Catalyzed Cycloisomerizations and Tandem Cycloadditions Forming Functionalized Azacyclic Arrays

  摘要：

  Cyclic ene-N-p-toluenesulfonamides tethered to an electron-deficient alkyne undergo cycloisomerizations readily under the influence of catalytic Pt(II) salts (PtCl2 or [dppbPtmu-OH](2)(BF4)(2)) or AgOTf. Yields for this process range from 47% to 99%. The resulting functionalized 2-azahydrindans can be reacted further using the Diels-Alder reaction. Tandem cycloisomerization-cycloaddition reactions in one pot generate highly functionalized 1-azadecalin ring systems in a highly stereocontrolled manner.

  DOI：

  10.1021/ol047696b
• 作为产物：
  描述：

  1-(toluene-4-sulfonyl)-1,2,3,4-tetrahydropyridine 在 bis-triphenylphosphine-palladium(II) chloride 甲醇 、 copper(l) iodide 、 溴 、 potassium carbonate 、 magnesium 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 、 三乙胺 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 83.0h， 生成 1-[2-(tert-butyldimethylsiloxy)phenyl]-5-[1-(toluene-4-sulfonyl)-1,2,3,6-tetrahydropyridin-4-yl]-pent-3-yn-1-one
  参考文献：
  名称：

  Pt(II) or Ag(I) Salt Catalyzed Cycloisomerizations and Tandem Cycloadditions Forming Functionalized Azacyclic Arrays

  摘要：

  Cyclic ene-N-p-toluenesulfonamides tethered to an electron-deficient alkyne undergo cycloisomerizations readily under the influence of catalytic Pt(II) salts (PtCl2 or [dppbPtmu-OH](2)(BF4)(2)) or AgOTf. Yields for this process range from 47% to 99%. The resulting functionalized 2-azahydrindans can be reacted further using the Diels-Alder reaction. Tandem cycloisomerization-cycloaddition reactions in one pot generate highly functionalized 1-azadecalin ring systems in a highly stereocontrolled manner.

  DOI：

  10.1021/ol047696b

文献信息

• Pt(II) or Ag(I) Salt Catalyzed Cycloisomerizations and Tandem Cycloadditions Forming Functionalized Azacyclic Arrays
  作者：Tyler J. Harrison、Gregory R. Dake

  DOI：10.1021/ol047696b

  日期：2004.12.1

  Cyclic ene-N-p-toluenesulfonamides tethered to an electron-deficient alkyne undergo cycloisomerizations readily under the influence of catalytic Pt(II) salts (PtCl2 or [dppbPtmu-OH](2)(BF4)(2)) or AgOTf. Yields for this process range from 47% to 99%. The resulting functionalized 2-azahydrindans can be reacted further using the Diels-Alder reaction. Tandem cycloisomerization-cycloaddition reactions in one pot generate highly functionalized 1-azadecalin ring systems in a highly stereocontrolled manner.