5-(tert-butyldimethylsilanyloxy)-isoquinoline | 872087-87-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 异喹啉及其衍生物
• 英文名称: 5-(tert-butyldimethylsilanyloxy)-isoquinoline
• 英文别名: Tert-butyl-isoquinolin-7-yloxy-dimethylsilane
• CAS: 872087-87-1
• 化学式: C₁₅H₂₁NOSi
• 分子量: 259.423
• InChiKey: AHSRXNFVPHCVPX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.62
• 重原子数：
  18
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  22.1
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  5-(tert-butyldimethylsilanyloxy)-isoquinoline 在 copper acetylacetonate 、 ammonium hydroxide 、 lithium chloro-isopropyl-magnesium chloride 、 caesium carbonate 、 乙酰丙酮 作用下， 以 四氢呋喃 、 N,N-二甲基甲酰胺 为溶剂， 反应 5.08h， 生成 1-amino-7-hydroxyisoquinoline
  参考文献：
  名称：

  Fragment based search for small molecule inhibitors of HIV-1 Tat-TAR

  摘要：

  Basic molecular building blocks such as benzene rings, amidines, guanidines, and amino groups have been combined in a systematic way to generate ligand candidates for HIV-1 TAR RNA. Ranking of the resulting compounds was achieved in a fluorimetric Tat-TAR competition assay. Although simple molecules such as phenylguanidine are inactive, few iteration steps led to a set of ligands with IC50 values ranging from 40 to 150 mu M. 1,7-Diaminoisoquinoline 17 and 2,4,6-triaminoquinazoline 22 have been further characterized by NMR titrations with TAR RNA. Compound 22 is bound to TAR at two high affinity sites and shows slow exchange between the free ligand and the RNA complex. These results encourage investigations of dimeric ligands built from two copies of compound 22 or related heterocycles. (C) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2014.11.004
• 作为产物：
  描述：

  7-羟基异喹啉 、 叔丁基二甲基氯硅烷 在 咪唑 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 48.0h， 以47%的产率得到5-(tert-butyldimethylsilanyloxy)-isoquinoline
  参考文献：
  名称：

  Fragment based search for small molecule inhibitors of HIV-1 Tat-TAR

  摘要：

  Basic molecular building blocks such as benzene rings, amidines, guanidines, and amino groups have been combined in a systematic way to generate ligand candidates for HIV-1 TAR RNA. Ranking of the resulting compounds was achieved in a fluorimetric Tat-TAR competition assay. Although simple molecules such as phenylguanidine are inactive, few iteration steps led to a set of ligands with IC50 values ranging from 40 to 150 mu M. 1,7-Diaminoisoquinoline 17 and 2,4,6-triaminoquinazoline 22 have been further characterized by NMR titrations with TAR RNA. Compound 22 is bound to TAR at two high affinity sites and shows slow exchange between the free ligand and the RNA complex. These results encourage investigations of dimeric ligands built from two copies of compound 22 or related heterocycles. (C) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2014.11.004

文献信息

• Enantioselective Thiourea-Catalyzed Acyl-Mannich Reactions of Isoquinolines
  作者：Mark S. Taylor、Norihito Tokunaga、Eric N. Jacobsen

  DOI：10.1002/anie.200502277

  日期：2005.10.21