tert-butyl 3-(2-azido-1,1-difluoro-ethyl)-5-benzyloxy-indole-1-carboxylate | 516521-92-9

• 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: tert-butyl 3-(2-azido-1,1-difluoro-ethyl)-5-benzyloxy-indole-1-carboxylate
• 英文别名: Tert-butyl 3-(2-azido-1,1-difluoroethyl)-5-phenylmethoxyindole-1-carboxylate
• CAS: 516521-92-9
• 化学式: C₂₂H₂₂F₂N₄O₃
• 分子量: 428.438
• InChiKey: FPVUNPNIHVADQA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.1
• 重原子数：
  31
• 可旋转键数：
  8
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.32
• 拓扑面积：
  54.8
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  tert-butyl 3-(2-azido-1,1-difluoro-ethyl)-5-benzyloxy-indole-1-carboxylate 在 palladium on activated charcoal 盐酸 、 氢气 作用下， 以 四氢呋喃 、 甲醇 、 乙醚 为溶剂， 反应 2.17h， 生成 3-(2-amino-1,1-difluoro-ethyl)-1H-indol-5-ol hydrochloride
  参考文献：
  名称：

  Syntheses of β,β-Difluorotryptamines

  摘要：

  Tryptamines disubstituted at the beta-position with fluorine have been synthesized as part of our research program to study the effects of fluorine substitution on the biological activities of neuroactive amines. Treatment of N-Boc-3-azidoacetyl indoles, prepared from readily available 2-chloracetylindoles, with dimethoxyethylamino sulfurtrifluoride produced the corresponding 3-(2-azido-1,1-difluoroethyl)indoles. Reduction of the azide to amine with hydrogen over Pd-C and careful removal of the N-Boc protecting group produced beta,beta-difluorotryptamines.

  DOI：

  10.1021/jo020731c
• 作为产物：
  描述：

  5-苄氧基吲哚 在 sodium hydroxide 、 sodium azide 、 [双(2-甲氧基乙基)胺]三氟化硫 作用下， 以 四氢呋喃 、 水 、 1,2-二氯乙烷 、 丙酮 、 甲苯 为溶剂， 反应 2.0h， 生成 tert-butyl 3-(2-azido-1,1-difluoro-ethyl)-5-benzyloxy-indole-1-carboxylate
  参考文献：
  名称：

  Syntheses of β,β-Difluorotryptamines

  摘要：

  Tryptamines disubstituted at the beta-position with fluorine have been synthesized as part of our research program to study the effects of fluorine substitution on the biological activities of neuroactive amines. Treatment of N-Boc-3-azidoacetyl indoles, prepared from readily available 2-chloracetylindoles, with dimethoxyethylamino sulfurtrifluoride produced the corresponding 3-(2-azido-1,1-difluoroethyl)indoles. Reduction of the azide to amine with hydrogen over Pd-C and careful removal of the N-Boc protecting group produced beta,beta-difluorotryptamines.

  DOI：

  10.1021/jo020731c

文献信息

• Syntheses of β,β-Difluorotryptamines
  作者：Wei-Ping Deng、Ghilsoo Nam、Junfa Fan、Kenneth L. Kirk

  DOI：10.1021/jo020731c

  日期：2003.4.1

  Tryptamines disubstituted at the beta-position with fluorine have been synthesized as part of our research program to study the effects of fluorine substitution on the biological activities of neuroactive amines. Treatment of N-Boc-3-azidoacetyl indoles, prepared from readily available 2-chloracetylindoles, with dimethoxyethylamino sulfurtrifluoride produced the corresponding 3-(2-azido-1,1-difluoroethyl)indoles. Reduction of the azide to amine with hydrogen over Pd-C and careful removal of the N-Boc protecting group produced beta,beta-difluorotryptamines.