methyl (E)-3-<2'-(4''-bromophenyl)-1'H-indol-3'-yl>prop-2-enoate | 130304-19-7

• 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: methyl (E)-3-<2'-(4''-bromophenyl)-1'H-indol-3'-yl>prop-2-enoate
• 英文别名: methyl (E)-3-(2-(4-bromophenyl)-1H-indol-3-yl)acrylate；methyl (E)-3-[2-(4-bromophenyl)-1H-indol-3-yl]prop-2-enoate
• CAS: 130304-19-7
• 化学式: C₁₈H₁₄BrNO₂
• 分子量: 356.219
• InChiKey: COYBEPLTPAKIRZ-ZHACJKMWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.7
• 重原子数：
  22
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.06
• 拓扑面积：
  42.1
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  methyl (E)-3-<2'-(4''-bromophenyl)-1'H-indol-3'-yl>prop-2-enoate 在 [Ir(dF(CF₃)ppy)2(dtbbpy)]PF₆ 作用下， 以 二氯甲烷 、 二甲基亚砜 为溶剂， 以83 %的产率得到3-bromo-11H-benzo[a]carbazole-5-carboxylic acid methyl ester
  参考文献：
  名称：

  Photocatalytic Dehydrogenative 6π‐Photocyclisation of Indole Derivatives via Successive Energy Transfer

  摘要：

  Herein, a successive energy transfer (sEnT) strategy to enable a dehydrogenative 6π‐photocyclisation, without the need for an external oxidant is reported, in which the energetically unfavourable dehydrogenation is driven by energy transfer. The valuable applicability of this method was demonstrated by the scaffold hopping of indole containing bioactive molecules, as well as by the succinct synthesis of naturally occurring tetracyclic furocarbazole alkaloids. Moreover, experimental and computational studies were conducted to elucidate the reaction mechanism.

  DOI：

  10.1002/adsc.202301174
• 作为产物：
  描述：

  3，3-二甲氧基丙酸甲酯 、 2-(4-溴苯基)-1H-吲哚 在 三氟乙酸 作用下， 以 二氯甲烷 为溶剂， 生成 methyl (E)-3-<2'-(4''-bromophenyl)-1'H-indol-3'-yl>prop-2-enoate
  参考文献：
  名称：

  Photocatalytic Dehydrogenative 6π‐Photocyclisation of Indole Derivatives via Successive Energy Transfer

  摘要：

  Herein, a successive energy transfer (sEnT) strategy to enable a dehydrogenative 6π‐photocyclisation, without the need for an external oxidant is reported, in which the energetically unfavourable dehydrogenation is driven by energy transfer. The valuable applicability of this method was demonstrated by the scaffold hopping of indole containing bioactive molecules, as well as by the succinct synthesis of naturally occurring tetracyclic furocarbazole alkaloids. Moreover, experimental and computational studies were conducted to elucidate the reaction mechanism.

  DOI：

  10.1002/adsc.202301174

文献信息

• Thermal 1,6-Electrocyclization Reactions of Acceptor-Substituted 2,3-Divinyl-1H-indoles Yielding Functionalized Carbazoles
  作者：Ulf Pindur、Reinhard Adam

  DOI：10.1002/hlca.19900730408

  日期：1990.6.20

  Three new synthetic procedures for and thermal 1,6-electrocyclizations of acceptor-substituted 2,3-divinyl-1H-indoles leading to functionalizing carbazoles are described. The scope and limitations as well as some mechanistic aspects of the methodologies are discussed. The key strategies employed include Pd(II)-catalyzed coupling and Wittig procedures.

  描述了三种新的合成方法，用于受体取代的2,3-二乙烯基-1 H-吲哚的1,6-电环化和热1,6-电环化，从而使咔唑官能化。讨论了方法的范围和局限性以及一些机械方面。所采用的关键策略包括Pd（II）催化的偶联和Wittig程序。
• PINDUR, ULF;ADAM, REINHARD, HELV. CHIM. ACTA, 73,(1990) N, C. 827-838
  作者：PINDUR, ULF、ADAM, REINHARD

  DOI：——

  日期：——