tert-butyl 3-(3-ethynylphenoxyl)propylcarbamate | 1192364-67-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: tert-butyl 3-(3-ethynylphenoxyl)propylcarbamate
• 英文别名: [3-(3-Ethynylphenoxy)-propyl]-carbamic acid tert-butyl ester；tert-butyl N-[3-(3-ethynylphenoxy)propyl]carbamate
• CAS: 1192364-67-2
• 化学式: C₁₆H₂₁NO₃
• 分子量: 275.348
• InChiKey: NPRPNEYBAQGOSY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  20
• 可旋转键数：
  8
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.44
• 拓扑面积：
  47.6
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  tert-butyl 3-(3-ethynylphenoxyl)propylcarbamate 、 ethyl (N⁴-benzoyl-5-iodocytosin-1-yl)acetate 在 bis-triphenylphosphine-palladium(II) chloride 、 copper(l) iodide 、 三乙胺 作用下， 以 N,N-二甲基甲酰胺 、 乙醇 为溶剂， 反应 36.0h， 以64%的产率得到ethyl 2-(6-(3-(3-(tert-butyloxycarbonylamino)propoxy)phenyl)-3H-pyrrolo[2,3-d]pyrimidin-2(7H)-on-3-yl)acetate
  参考文献：
  名称：

  Peptide Nucleic Acid Containing a Meta-Substituted Phenylpyrrolocytosine Exhibits a Fluorescence Response and Increased Binding Affinity toward RNA

  摘要：

  Peptide nucleic acids (PNA) containing meta-substituted 6-phenylpyrrolocytosine (PhpC), [mono-m)-(aminoethoxy)phenyl]pyrrolocytosine (mmePhpC), [mono-m-(aminopropoxy)phenyl]pyrrolocytosine (mmpPhpC), and [mono-m-(guanidinoethoxy)phenyl]pyrrolocytosine (mmguaPhpC), have been synthesized. Meta-substituted PhpCs have been hybridized with overall higher binding affinity toward DNA and RNA than previously synthesized moePhpC or newly synthesized mopPhpC. The guanidinium-containing nucleobase, mmguaPhpC, exhibited the highest increase in binding affinity toward RNA while fluorometrically responding on the state of hybridization.

  DOI：

  10.1021/ol9019474
• 作为产物：
  描述：

  在 甲醇 、 potassium carbonate 作用下， 反应 1.5h， 生成 tert-butyl 3-(3-ethynylphenoxyl)propylcarbamate
  参考文献：
  名称：

  Peptide Nucleic Acid Containing a Meta-Substituted Phenylpyrrolocytosine Exhibits a Fluorescence Response and Increased Binding Affinity toward RNA

  摘要：

  Peptide nucleic acids (PNA) containing meta-substituted 6-phenylpyrrolocytosine (PhpC), [mono-m)-(aminoethoxy)phenyl]pyrrolocytosine (mmePhpC), [mono-m-(aminopropoxy)phenyl]pyrrolocytosine (mmpPhpC), and [mono-m-(guanidinoethoxy)phenyl]pyrrolocytosine (mmguaPhpC), have been synthesized. Meta-substituted PhpCs have been hybridized with overall higher binding affinity toward DNA and RNA than previously synthesized moePhpC or newly synthesized mopPhpC. The guanidinium-containing nucleobase, mmguaPhpC, exhibited the highest increase in binding affinity toward RNA while fluorometrically responding on the state of hybridization.

  DOI：

  10.1021/ol9019474

文献信息

• Peptide Nucleic Acid Containing a Meta-Substituted Phenylpyrrolocytosine Exhibits a Fluorescence Response and Increased Binding Affinity toward RNA
  作者：Filip Wojciechowski、Robert H. E. Hudson

  DOI：10.1021/ol9019474

  日期：2009.11.5

  Peptide nucleic acids (PNA) containing meta-substituted 6-phenylpyrrolocytosine (PhpC), [mono-m)-(aminoethoxy)phenyl]pyrrolocytosine (mmePhpC), [mono-m-(aminopropoxy)phenyl]pyrrolocytosine (mmpPhpC), and [mono-m-(guanidinoethoxy)phenyl]pyrrolocytosine (mmguaPhpC), have been synthesized. Meta-substituted PhpCs have been hybridized with overall higher binding affinity toward DNA and RNA than previously synthesized moePhpC or newly synthesized mopPhpC. The guanidinium-containing nucleobase, mmguaPhpC, exhibited the highest increase in binding affinity toward RNA while fluorometrically responding on the state of hybridization.