3-(buta-1,3-dien-1-yl)-1-tosyl-1H-indole | 1175163-51-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 3-(buta-1,3-dien-1-yl)-1-tosyl-1H-indole
• CAS: 1175163-51-5
• 化学式: C₁₉H₁₇NO₂S
• 分子量: 323.415
• InChiKey: FLLLKFGZLYOMEE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.39
• 重原子数：
  23.0
• 可旋转键数：
  4.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.05
• 拓扑面积：
  39.07
• 氢给体数：
  0.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  3-(buta-1,3-dien-1-yl)-1-tosyl-1H-indole 、 methyl 2-[(4-fluorophenyl)methylideneamino]propanoate 在 tetrakis(actonitrile)copper(I) hexafluorophosphate 、 C₃₅H₅₇FeP₂Pd⁽¹⁺⁾*BF₄^(1-) 、 C₃₁H₂₆FeNOP 、 三乙胺 作用下， 以 四氢呋喃 为溶剂， 反应 48.0h， 以96%的产率得到(2S,3R,E)-methyl 2-amino-2,3-dimethyl-5-(1-tosyl-1H-indol-3-yl)pent-4-enoate
  参考文献：
  名称：

  Stereodivergent Coupling of 1,3-Dienes with Aldimine Esters Enabled by Synergistic Pd and Cu Catalysis

  摘要：

  Herein we describe the use of synergistic Pd and Cu catalysis for stereodivergent coupling reactions between 1,3-dienes and aldimine esters. By using different enantiomers of the two metal catalysts, all four stereo-isomers of the coupling products, which have two vicinal stereocenters, could be accessed with high diastereo- and enantioselectivity. This atom-economical cross-coupling reaction has a wide substrate scope and good functional group tolerance. Our work highlights the power of synergistic catalysis for asymmetric coupling reactions involving Pd-hydride catalysts.

  DOI：

  10.1021/jacs.9b07600
• 作为产物：
  描述：

  1-[(4-甲基苯基)磺酰]-1H-吲哚-3-甲醛 、 烯丙基三苯基溴化膦 在 potassium tert-butylate 作用下， 以 乙醚 为溶剂， 反应 0.25h， 生成 3-(buta-1,3-dien-1-yl)-1-tosyl-1H-indole
  参考文献：
  名称：

  Cobalt-Catalyzed 1,4-Hydrovinylation of Styrenes and 1-Aryl-1,3-butadienes

  摘要：

  The application of aryl-substituted starting materials such as styrene and 1-aryl-substituted 1,3-butadiene derivatives in the cobalt-catalyzed 1,4-hydrovinylation reaction has been investigated. The use of unsymmetrical alpha,omega-dienes in the hydrovinylation with 1-aryl-1,3-butadiene led chemoselectively to the 1:1 or the 1:2 adducts depending on the stoichiometry of the starting materials.

  DOI：

  10.1021/ol901064p

文献信息

• Visible-Light-Induced Photoredox-Catalyzed Selective 1,4-Difluoroalkylesterification of 1-Aryl-1,3-dienes
  作者：Ming-Hang Bi、Ying Cheng、Wen-Jing Xiao、Jia-Rong Chen

  DOI：10.1021/acs.orglett.2c03020

  日期：2022.10.21

  photoredox and copper catalysis is described. This protocol uses commercially available CF2-reagents as radical precursors and carboxylic acids as oxygen-based nucleophiles, providing access to difluoroalkylated allylic esters. This protocol could be extended to intramolecular two-component 1,4-difluoroalkylesterification to access 3-substituted benzobutyrolactones. Preliminary mechanistic studies support

  描述了通过双光氧化还原和铜催化实现的 1-芳基-1,3-二烯的选择性三组分 1,4-二氟烷基酯化。该协议使用市售的 CF 2试剂作为自由基前体，使用羧酸作为氧基亲核试剂，从而提供对二氟烷基化烯丙酯的访问。该协议可以扩展到分子内双组分 1,4-二氟烷基酯化以获取 3-取代苯并丁内酯。初步的机械研究支持一个激进的过程。
• Organocatalytic photoinduced carboamination of dienes
  作者：Arun Yadav、Sabhya Sandha、Chandra Bhushan Tripathi

  DOI：10.1039/d3cc01121f

  日期：——

  2-carbofunctionalization strategy for conjugated dienes has been developed. No exogenous photocatalyst or additives are required in this mild protocol and it allows for highly regioselective and efficient 1,2-carboisothiocyanation through the coupling of a diene, an alkyl radical and TMSNCS. The reaction is proposed to proceed through EDA complexation between the diene and TMSNCS.

  已开发出共轭二烯的有机催化光诱导 1,2-碳官能化策略。这种温和的方案不需要外源光催化剂或添加剂，它允许通过二烯、烷基自由基和 TMSNCS 的偶联进行高度区域选择性和高效的 1,2-碳异硫氰化。该反应被提议通过二烯和 TMSNCS 之间的 EDA 络合进行。