1-benzyl-5-vinyl-1H-indole | 63228-23-9

• 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: 1-benzyl-5-vinyl-1H-indole
• 英文别名: 1-Benzyl-5-ethenyl-1H-indole；1-benzyl-5-ethenylindole
• CAS: 63228-23-9
• 化学式: C₁₇H₁₅N
• 分子量: 233.313
• InChiKey: UPFCAOVZOHEFLF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.4
• 重原子数：
  18
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.06
• 拓扑面积：
  4.9
• 氢给体数：
  0
• 氢受体数：
  0

反应信息

• 作为反应物：
  描述：

  1-benzyl-5-vinyl-1H-indole 在 4,5-二氮芴-9-酮 、 双氧水 、 palladium diacetate 、 三氟乙酸 作用下， 以 四氢呋喃 、 水 为溶剂， 反应 6.0h， 以74%的产率得到1-(1-benzyl-1H-indol-5-yl)-2-hydroxyethan-1-one
  参考文献：
  名称：

  Dual Role of H₂O₂ in Palladium-Catalyzed Dioxygenation of Terminal Alkenes

  摘要：

  A pallaclium-catalyzed, environmentally friendly dioxygenation reaction of simple alkenes has been developed that enabled rapid assembly of valuable a-hydroxy ketones with high atom economy. Notably, control experiments and 180 isotope-labeling experiments established that H2O2 played a dominant dual role in this transformation.

  DOI：

  10.1021/acs.orglett.7b01228
• 作为产物：
  描述：

  5-溴吲哚 在 1,1'-双(二苯膦基)二茂铁二氯化钯(II)二氯甲烷复合物 、 sodium hydride 、 caesium carbonate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 20.17h， 生成 1-benzyl-5-vinyl-1H-indole
  参考文献：
  名称：

  通过1,3-偶极环加成反应合成衍生自乙烯基吲哚/吲唑的螺吡咯烷类似物。

  摘要：

  通过一锅多组分合成已经完成了一系列新的含有吡咯/吲唑部分作为侧链的螺并吡咯烷化合物。该方法使用了N-烷基乙烯基吲哚/吲唑与由环/无环氨基酸原位制备的偶氮甲亚胺之间的1,3-偶极环加成反应。1,3-偶极环加成反应在热条件下有效进行，从而提供区域和立体有规的环状加合物。

  DOI：

  10.3762/bjoc.12.288

文献信息

• Suzuki−Miyaura Cross-Coupling Reactions of Potassium Vinyltrifluoroborate with Aryl and Heteroaryl Electrophiles
  作者：Gary A. Molander、Adam R. Brown

  DOI：10.1021/jo0617013

  日期：2006.12.1

  We have previously reported that the palladium-catalyzed cross-coupling reaction of potassium vinyltrifluoroborate with aryl electrophiles proceeds with good yields. Herein, we describe recent progress in optimizing the reaction, as well as outlining the scope and limitations of the reaction. The cross-coupling reaction can generally be effected using 2 mol % of PdCl2 and 6 mol % of PPh3 as a catalyst system in THF/H2O with Cs2CO3 as a base. Moderate to good yields are obtained in the presence of a variety of functional groups.
• Heck Coupling Using a Vinyliodo-MIDA Boronate: An Efficient and Modular Access to Polyene Frameworks
  作者：Johan Cornil、Pierre-Georges Echeverria、Phannarath Phansavath、Virginie Ratovelomanana-Vidal、Amandine Guérinot、Janine Cossy

  DOI：10.1021/acs.orglett.5b00042

  日期：2015.2.20

  A simple Heck coupling between an alkenyl iodo-boronate and a variety of terminal olefins is disclosed. This method gives access to a wide range of dienic moieties including valuable bis-functionalized dienes. The synthetic potential of the coupling reaction is demonstrated by a short and modular preparation of several tetraenic compounds.
• Multicomponent synthesis of spiropyrrolidine analogues derived from vinylindole/indazole by a 1,3-dipolar cycloaddition reaction
  作者：Manjunatha Narayanarao、Lokesh Koodlur、Vijayakumar G Revanasiddappa、Subramanya Gopal、Susmita Kamila

  DOI：10.3762/bjoc.12.288

  日期：——

  A new series of spiropyrrolidine compounds containing indole/indazole moieties as side chains have been accomplished via a one-pot multicomponent synthesis. The method uses the 1,3-dipolar cycloaddition reaction between N-alkylvinylindole/indazole and azomethine ylides, prepared in situ from cyclic/acyclic amino acids. The 1,3-dipolar cycloaddition proceeds efficiently under thermal conditions to afford

  通过一锅多组分合成已经完成了一系列新的含有吡咯/吲唑部分作为侧链的螺并吡咯烷化合物。该方法使用了N-烷基乙烯基吲哚/吲唑与由环/无环氨基酸原位制备的偶氮甲亚胺之间的1,3-偶极环加成反应。1,3-偶极环加成反应在热条件下有效进行，从而提供区域和立体有规的环状加合物。
• Dual Role of H₂O₂ in Palladium-Catalyzed Dioxygenation of Terminal Alkenes
  作者：Jiuzhong Huang、Jianxiao Li、Jia Zheng、Wanqing Wu、Weigao Hu、Lu Ouyang、Huanfeng Jiang

  DOI：10.1021/acs.orglett.7b01228

  日期：2017.7.7

  A pallaclium-catalyzed, environmentally friendly dioxygenation reaction of simple alkenes has been developed that enabled rapid assembly of valuable a-hydroxy ketones with high atom economy. Notably, control experiments and 180 isotope-labeling experiments established that H2O2 played a dominant dual role in this transformation.