1-(1-(tert-butyldimethylsilyl)-1H-indol-6-yl)-2,2,2-trifluoroethanone | 1430331-80-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吲哚及其衍生物
• 英文名称: 1-(1-(tert-butyldimethylsilyl)-1H-indol-6-yl)-2,2,2-trifluoroethanone
• 英文别名: 1-[1-[Tert-butyl(dimethyl)silyl]indol-6-yl]-2,2,2-trifluoroethanone；1-[1-[tert-butyl(dimethyl)silyl]indol-6-yl]-2,2,2-trifluoroethanone
• CAS: 1430331-80-8
• 化学式: C₁₆H₂₀F₃NOSi
• 分子量: 327.422
• InChiKey: SMFYRXAILCROPT-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.24
• 重原子数：
  22
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.44
• 拓扑面积：
  22
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  1-(1-(tert-butyldimethylsilyl)-1H-indol-6-yl)-2,2,2-trifluoroethanone 在 吡啶 、 盐酸羟胺 、 氨 、 碘 、 三乙胺 作用下， 以 乙醇 、 二氯甲烷 、 甲基叔丁基醚 为溶剂， 反应 4.0h， 生成 1-(tert-butyldimethylsilyl)-6-(3-(trifluoromethyl)diaziridin-3-yl)-1H-indole
  参考文献：
  名称：

  L-Phototryptophan

  摘要：

  AbstractPhototryptophan is a new photoactivatable amino acid designed to be incorporated into tryptophan‐containing peptides for photoaffinity labeling. The synthesis of phototryptophan starts from 6‐bromoindole with the installation of an 1‐azi‐2,2,2‐trifluoroethyl moiety, followed by microwave‐assisted condensation with serine under mild conditions. Separation of the N‐acetylated enantiomers was possible by employing Aspergillus aminoacylase. Differential scanning calorimetry showed that phototryptophan is thermally stable up to 100 °C. Boc‐L‐Phototryptophan was used to assemble a diazirine analog of the marine natural product hemiasterlin.

  DOI：

  10.1002/ejoc.201201726
• 作为产物：
  描述：

  6-溴吲哚 、 三氟乙酸乙酯 、 叔丁基二甲基氯硅烷 在 正丁基锂 、 叔丁基锂 作用下， 以 四氢呋喃 、 正己烷 、 正戊烷 为溶剂， 反应 4.42h， 以80%的产率得到1-(1-(tert-butyldimethylsilyl)-1H-indol-6-yl)-2,2,2-trifluoroethanone
  参考文献：
  名称：

  L-Phototryptophan

  摘要：

  AbstractPhototryptophan is a new photoactivatable amino acid designed to be incorporated into tryptophan‐containing peptides for photoaffinity labeling. The synthesis of phototryptophan starts from 6‐bromoindole with the installation of an 1‐azi‐2,2,2‐trifluoroethyl moiety, followed by microwave‐assisted condensation with serine under mild conditions. Separation of the N‐acetylated enantiomers was possible by employing Aspergillus aminoacylase. Differential scanning calorimetry showed that phototryptophan is thermally stable up to 100 °C. Boc‐L‐Phototryptophan was used to assemble a diazirine analog of the marine natural product hemiasterlin.

  DOI：

  10.1002/ejoc.201201726

文献信息

• <scp>L</scp>-Phototryptophan
  作者：Thomas Wartmann、Thomas Lindel

  DOI：10.1002/ejoc.201201726

  日期：2013.3

  AbstractPhototryptophan is a new photoactivatable amino acid designed to be incorporated into tryptophan‐containing peptides for photoaffinity labeling. The synthesis of phototryptophan starts from 6‐bromoindole with the installation of an 1‐azi‐2,2,2‐trifluoroethyl moiety, followed by microwave‐assisted condensation with serine under mild conditions. Separation of the N‐acetylated enantiomers was possible by employing Aspergillus aminoacylase. Differential scanning calorimetry showed that phototryptophan is thermally stable up to 100 °C. Boc‐L‐Phototryptophan was used to assemble a diazirine analog of the marine natural product hemiasterlin.