1′-(2-azidoethyl)spiro[[1,3]dioxolane-2,3′-indolin]-2′-one | 1478979-82-6

• 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′-(2-azidoethyl)spiro[[1,3]dioxolane-2,3′-indolin]-2′-one
• 英文别名: 1'-(2-Azidoethyl)spiro[1,3-dioxolane-2,3'-indoline]-2'-one；1'-(2-azidoethyl)spiro[1,3-dioxolane-2,3'-indole]-2'-one
• CAS: 1478979-82-6
• 化学式: C₁₂H₁₂N₄O₃
• 分子量: 260.252
• InChiKey: PMHAUEKJBCQCNL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  19
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  53.1
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  二茂铁乙炔 、 1′-(2-azidoethyl)spiro[[1,3]dioxolane-2,3′-indolin]-2′-one 在 copper(ll) sulfate pentahydrate 、 sodium ascorbate 作用下， 以 乙醇 、 水 为溶剂， 以78%的产率得到1′-(2-(4-ferrocenyl-1H-1,2,3-triazol-1-yl)ethyl)spiro[[1,3]-dioxolane-2,3′-indolin]-2′-one
  参考文献：
  名称：

  Base-Promoted Expedient Access to Spiroisatins: Synthesis and Antitubercular Evaluation of 1H-1,2,3-Triazole-Tethered Spiroisatin–Ferrocene and Isatin–Ferrocene Conjugates

  摘要：

  The use of sodium hydride provides a convenient access to the synthesis of C-5-functionalized spiroisatins with the absence of the typical drawbacks associated with conventional protocols. The synthesized precursors, viz. N-alkylazido spiroisatins and their unprotected counterparts, were explored in Cu-mediated azide alkyne cycloaddition reactions to probe the antitubercular structure-activity relationships (SAR) within the isatin ferrocene-triazole conjugate family. The antitubercular evaluation studies of the synthesized conjugates revealed an improvement in the minimal inhibitory concentration (MIC) with the introduction of ferrocene nucleus, as evidenced by spiroisatin ferrocene and isatin ferrocene hybrids.

  DOI：

  10.1021/om4009229
• 作为产物：
  描述：

  1'-(2-Bromoethyl)spiro[1,3-dioxolane-2,3'-indol]-2'(1'h)-one 在 sodium azide 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 1.0h， 生成 1′-(2-azidoethyl)spiro[[1,3]dioxolane-2,3′-indolin]-2′-one
  参考文献：
  名称：

  Base-Promoted Expedient Access to Spiroisatins: Synthesis and Antitubercular Evaluation of 1H-1,2,3-Triazole-Tethered Spiroisatin–Ferrocene and Isatin–Ferrocene Conjugates

  摘要：

  The use of sodium hydride provides a convenient access to the synthesis of C-5-functionalized spiroisatins with the absence of the typical drawbacks associated with conventional protocols. The synthesized precursors, viz. N-alkylazido spiroisatins and their unprotected counterparts, were explored in Cu-mediated azide alkyne cycloaddition reactions to probe the antitubercular structure-activity relationships (SAR) within the isatin ferrocene-triazole conjugate family. The antitubercular evaluation studies of the synthesized conjugates revealed an improvement in the minimal inhibitory concentration (MIC) with the introduction of ferrocene nucleus, as evidenced by spiroisatin ferrocene and isatin ferrocene hybrids.

  DOI：

  10.1021/om4009229

文献信息

• Base-Promoted Expedient Access to Spiroisatins: Synthesis and Antitubercular Evaluation of 1<i>H</i>-1,2,3-Triazole-Tethered Spiroisatin–Ferrocene and Isatin–Ferrocene Conjugates
  作者：Kewal Kumar、Christophe Biot、Séverine Carrère-Kremer、Laurent Kremer、Yann Guérardel、Pascal Roussel、Vipan Kumar

  DOI：10.1021/om4009229

  日期：2013.12.23

  The use of sodium hydride provides a convenient access to the synthesis of C-5-functionalized spiroisatins with the absence of the typical drawbacks associated with conventional protocols. The synthesized precursors, viz. N-alkylazido spiroisatins and their unprotected counterparts, were explored in Cu-mediated azide alkyne cycloaddition reactions to probe the antitubercular structure-activity relationships (SAR) within the isatin ferrocene-triazole conjugate family. The antitubercular evaluation studies of the synthesized conjugates revealed an improvement in the minimal inhibitory concentration (MIC) with the introduction of ferrocene nucleus, as evidenced by spiroisatin ferrocene and isatin ferrocene hybrids.