2-O-(tert-butyldimethyl)silyl-3-O-(trifluoromethanesulfonyloxy)naphthalene | 342890-22-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 2-O-(tert-butyldimethyl)silyl-3-O-(trifluoromethanesulfonyloxy)naphthalene
• 英文别名: [3-[Tert-butyl(dimethyl)silyl]oxynaphthalen-2-yl] trifluoromethanesulfonate；[3-[tert-butyl(dimethyl)silyl]oxynaphthalen-2-yl] trifluoromethanesulfonate
• CAS: 342890-22-6
• 化学式: C₁₇H₂₁F₃O₄SSi
• 分子量: 406.498
• InChiKey: QTJDQQOZWNKZTL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.45
• 重原子数：
  26
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.41
• 拓扑面积：
  61
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  2-O-(tert-butyldimethyl)silyl-3-O-(trifluoromethanesulfonyloxy)naphthalene 在 四丁基氟化铵 作用下， 以 二氯甲烷 为溶剂， 反应 1.0h， 以83%的产率得到2-O-(trifluoromethanesulfonyloxy)-3-hydroxynaphthalene
  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：

  2,3-二羟基萘 在 三乙胺 作用下， 以 乙腈 为溶剂， 反应 2.0h， 生成 2-O-(tert-butyldimethyl)silyl-3-O-(trifluoromethanesulfonyloxy)naphthalene
  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

文献信息

• Photochemically Removable Silyl Protecting Groups
  作者：Michael C. Pirrung、Lara Fallon、Jin Zhu、Yong Rok Lee

  DOI：10.1021/ja002370t

  日期：2001.4.1

  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.