1'-(3-Bromopropyl)spiro[1,3-dioxolane-2,3'-indole]-2'-one | 883658-82-0

• 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'-(3-Bromopropyl)spiro[1,3-dioxolane-2,3'-indole]-2'-one
• CAS: 883658-82-0
• 化学式: C₁₃H₁₄BrNO₃
• 分子量: 312.163
• InChiKey: NSTKOJBUROOLTF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  18
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.46
• 拓扑面积：
  38.8
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  1'-(3-Bromopropyl)spiro[1,3-dioxolane-2,3'-indole]-2'-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′-(3-azidopropyl)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：

  靛红 在 sodium hydride 、 potassium carbonate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 6.59h， 生成 1'-(3-Bromopropyl)spiro[1,3-dioxolane-2,3'-indole]-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

• Catalytic Asymmetric Homologation of Ketones with α-Alkyl α-Diazo Esters
  作者：Fei Tan、Maoping Pu、Jun He、Jinzhao Li、Jian Yang、Shunxi Dong、Xiaohua Liu、Yun-Dong Wu、Xiaoming Feng

  DOI：10.1021/jacs.0c12683

  日期：2021.2.10

  derivatives with α-alkyl α-diazo esters utilizing a chiral scandium(III) N,N′-dioxide as the Lewis acid catalyst. This reaction supplies a highly chemo-, regio-, and enantioselective pathway for the synthesis of optically active β-keto esters with an all-carbon quaternary center through highly selective alkyl-group migration of the ketones. Moreover, the ring expansion of cyclic ketones was accomplished under

  酮与重氮化合物的同源性是合成单碳扩链无环酮或扩环环酮的有用策略。然而，由于较低的反应性和复杂的选择性，无环酮与α-重氮酯的不对称同源性仍然是一个挑战。在此，我们报道了利用手性scan（III）N，N与N -α-烷基α-重氮酯对苯乙酮和相关衍生物的对映选择性催化同源性'-二氧化物为路易斯酸催化剂。该反应提供了高度化学，区域和对映体选择性的途径，用于通过酮的高选择性烷基基团迁移来合成具有全碳季中心的旋光性β-酮酯。此外，环状酮的扩环是在稍微修饰的条件下完成的，从而提供了一系列对映体富集的环状β-酮酯。已经进行了密度泛函理论计算，以阐明可以解释所观察到的区域和对映选择性的反应途径和可能的工作模型。
• 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.