4-(tert-Butyldimethylsiloxy)-2,6-xylyl isocyanide | 152457-11-9

• 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: 4-(tert-Butyldimethylsiloxy)-2,6-xylyl isocyanide
• 英文别名: Tert-butyl-(4-isocyano-3,5-dimethylphenoxy)-dimethylsilane
• CAS: 152457-11-9
• 化学式: C₁₅H₂₃NOSi
• 分子量: 261.439
• InChiKey: NJEPTDLXNXQHDW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.24
• 重原子数：
  18
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.53
• 拓扑面积：
  13.6
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  4-(tert-Butyldimethylsiloxy)-2,6-xylyl isocyanide 在 四丁基氟化铵 、 2,3-二氯-5,6-二氰基-1,4-苯醌 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 1.5h， 生成
  参考文献：
  名称：

  Stereoselective synthesis of 2-amino alcohols by use of an isocyanide as an aminomethylene equivalent

  摘要：

  Preparation of an isocyanide having a removable N-substituent and its application to the stereoselective synthesis of 2-amino alcohols are described. 4-(tert-Butyldimethylsiloxy)-2,6-xylyl isocyanide was prepared from commercially available 3,5-xylenol. The isocyanide underwent a samarium iodide-mediated coupling reaction with organic halides and carbonyl compounds. Reduction of the reaction mixture with NaBH4 selectively afforded anti 2-(arylamino) alcohols, which were then deprotected to the corresponding 2-(primary amino) alcohols via desilylation with TBAF followed by oxidation with DDQ. A ceramide was successfully synthesized by use of the present stereoselective synthetic method for 2-amino alcohols, demonstrating a new synthetic utility of the isocyanide as an aminomethylene equivalent.

  DOI：

  10.1021/jo00076a042
• 作为产物：
  描述：

  3,5-二甲基-4-氨基苯酚 在 三乙胺 、 氯甲酸三氯甲酯 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 、 甲苯 为溶剂， 反应 26.0h， 生成 4-(tert-Butyldimethylsiloxy)-2,6-xylyl isocyanide
  参考文献：
  名称：

  Stereoselective synthesis of 2-amino alcohols by use of an isocyanide as an aminomethylene equivalent

  摘要：

  Preparation of an isocyanide having a removable N-substituent and its application to the stereoselective synthesis of 2-amino alcohols are described. 4-(tert-Butyldimethylsiloxy)-2,6-xylyl isocyanide was prepared from commercially available 3,5-xylenol. The isocyanide underwent a samarium iodide-mediated coupling reaction with organic halides and carbonyl compounds. Reduction of the reaction mixture with NaBH4 selectively afforded anti 2-(arylamino) alcohols, which were then deprotected to the corresponding 2-(primary amino) alcohols via desilylation with TBAF followed by oxidation with DDQ. A ceramide was successfully synthesized by use of the present stereoselective synthetic method for 2-amino alcohols, demonstrating a new synthetic utility of the isocyanide as an aminomethylene equivalent.

  DOI：

  10.1021/jo00076a042

文献信息

• Regio- and Stereoselective Incorporation of a¹³<i>C</i>Nuclide into D-<i>ribo</i>-Phytosphingosine<i>via</i>SmI₂-Mediated C–C Formation with¹³<i>C</i>-Labeled Isocyanide
  作者：Masahiro Murakami、Hajime Ito、Yoshihiko lto

  DOI：10.1246/cl.1996.185

  日期：1996.3

  Preparation of a 13C-labeled isocyanide and its application to the total synthesis of [2-13C]D-ribo-C18-phytosphingosine are described. The synthesis of the labeled phytosphingosine is based on the use of the isocyanide as a 13CH–NH2 precursor in the SmI2-mediated three-component coupling reaction, wherein regio- and stereoselective incorporation of a 13C nuclide in the carbon skeleton is achieved

  描述了 13 C 标记的异氰化物的制备及其在 [2-13 C] D-核糖-C18-植物鞘氨醇全合成中的应用。标记植物鞘氨醇的合成基于在 SmI2 介导的三组分偶联反应中使用异氰化物作为 13CH-NH2 前体，其中 13C 核素在碳骨架中的区域和立体选择性掺入实现。