2-iodo-5-diethyiaminophenyl acetate | 342890-09-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚酯
• 英文名称: 2-iodo-5-diethyiaminophenyl acetate
• CAS: 342890-09-9
• 化学式: C₁₂H₁₆INO₂
• 分子量: 333.169
• InChiKey: GKENCRJLDMIRAC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.06
• 重原子数：
  16.0
• 可旋转键数：
  4.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  29.54
• 氢给体数：
  0.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  2-iodo-5-diethyiaminophenyl acetate 在 dihydrogen hexachloroplatinate 、 copper(l) iodide 、 四(三苯基膦)钯 、 triethylamine trihydrofluoride 、 三乙胺 作用下， 以 四氢呋喃 、 异丙醇 、 乙腈 为溶剂， 生成 6-acetoxy-4-diethylamino-trans-β-[diisopropyl(3'-O-acetyl-thymidin-yl)silyl]styrene
  参考文献：
  名称：

  Photochemically Removable Silyl Protecting Groups

  摘要：

  Several o-phenol-containing alkoxyvinylsilanes were prepared and their photochemistry was investigated. These materials were prepared via hydrosilylation of the corresponding o-acetoxy arylacetylenes. Two major classes of photochemical processes were identified in these reactants: trans --> cia isomerization, leading to an intramolecular nucleophilic substitution process at silicon, and 1,5-silyl shift, leading to an unsymmetrical dialkoxysilane. The major outcome of this work is a novel class of photochemically removable protecting groups. Two alkyl substitutions on silicon, the dimethyl and diisopropyl, were examined. The latter is more stable and is preferred for protecting groups that must tolerate multiple steps or reagents. Protection of alcohols is generally performed starting with the arylethynyl acetate, which can be subjected to hydrosilylation, alcohol substitution, and acetate deprotection without isolation of intermediates. Two groups were studied in detail, the phenol and 2 naphthol Vinyl silane derivatives. A variety of primary and secondary alcohols were protected with these reagents. These groups can be deprotected cleanly and in high yield by irradiation from 250 to 350 nm.

  DOI：

  10.1021/ja002370t
• 作为产物：
  描述：

  M-(二乙基氨基)苯基乙酸酯 在 碘 、 thallium(I) acetate 作用下， 以 二氯甲烷 为溶剂， 以78%的产率得到2-iodo-5-diethyiaminophenyl acetate
  参考文献：
  名称：

  Photochemically Removable Silyl Protecting Groups

  摘要：

  Several o-phenol-containing alkoxyvinylsilanes were prepared and their photochemistry was investigated. These materials were prepared via hydrosilylation of the corresponding o-acetoxy arylacetylenes. Two major classes of photochemical processes were identified in these reactants: trans --> cia isomerization, leading to an intramolecular nucleophilic substitution process at silicon, and 1,5-silyl shift, leading to an unsymmetrical dialkoxysilane. The major outcome of this work is a novel class of photochemically removable protecting groups. Two alkyl substitutions on silicon, the dimethyl and diisopropyl, were examined. The latter is more stable and is preferred for protecting groups that must tolerate multiple steps or reagents. Protection of alcohols is generally performed starting with the arylethynyl acetate, which can be subjected to hydrosilylation, alcohol substitution, and acetate deprotection without isolation of intermediates. Two groups were studied in detail, the phenol and 2 naphthol Vinyl silane derivatives. A variety of primary and secondary alcohols were protected with these reagents. These groups can be deprotected cleanly and in high yield by irradiation from 250 to 350 nm.

  DOI：

  10.1021/ja002370t