2-bromo-1-(3,5-dimethylphenyl)-1H-indene | 1454309-43-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 茚和异茚
• 英文名称: 2-bromo-1-(3,5-dimethylphenyl)-1H-indene
• CAS: 1454309-43-3
• 化学式: C₁₇H₁₅Br
• 分子量: 299.21
• InChiKey: MZKUYKBKXWZBDU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.3
• 重原子数：
  18
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  0
• 氢给体数：
  0
• 氢受体数：
  0

反应信息

• 作为产物：
  描述：

  (E)-1,3-dimethyl-5-styrylbenzene 在 silver tetrafluoroborate 、 苄基三乙基氯化铵 、 sodium hydroxide 作用下， 以 水 、 1,2-二氯乙烷 为溶剂， 反应 23.0h， 生成 2-bromo-5,7-dimethyl-1-phenyl-1H-indene 、 2-bromo-1-(3,5-dimethylphenyl)-1H-indene
  参考文献：
  名称：

  Synthesis of 2-bromo-1-aryl-1H-indenes via a Ag(I) promoted domino 2π-electrocyclic ring-opening/4π-electrocyclization reaction of 1,2-diaryl substituted gem-dibromocyclopropanes

  摘要：

  2-Bromo-1-aryl substituted indenes can be synthesized from 1,2-diaryl substituted gem-dibromocyclopropanes via a domino reaction sequence. The cascade reaction involves silver(I) promoted ionization and 2 pi-disrotatory electrocyclic ring-opening, followed by a 4 pi-conrotatory electrocyclic ring closing reaction of the allylic carbocation intermediate. Reaction conditions utilize silver tetrafluoroborate (AgBF4) in dichloroethane at 65 degrees C. Selectivity effects for the electrocyclization were also studied. The 2-bromoindenes can be further functionalized using cross-coupling reactions, such as the Suzuki-Miyaura protocol. The alkene it-bond of the indenes can also be isomerized to give the thermodynamically more stable 2-bromo-3-aryl-1H-indene isomers using triethylamine in dichloromethane at room temperature. (C) 2013 Published by Elsevier Ltd.

  DOI：

  10.1016/j.tet.2013.07.086

文献信息

• [EN] THE CROSS COUPLING OF 2-BROMO-1-PHENYL INDENES WITH PHENYL ACETYLENES AND OTHER SUBSTITUTED ACETYLENES IN WATER<br/>[FR] COUPLAGE CROISÉ DE 2-BROMO-1-PHÉNYL-INDÈNES AVEC DES PHÉNYL-ACÉTYLÈNES ET AUTRES ACÉTYLÈNES SUBSTITUÉS DANS L'EAU
  申请人：ROSOCHA YAROSLAV GREGORY

  公开号：WO2014064478A1

  公开（公告）日：2014-05-01

  The cross-coupling reaction of 2-bromo-1 -phenyl indenes with phenyl acetylenes or propargyl alcohol is disclosed. The cross-coupling reaction uses a palladium catalyst with triphenylphosphine in the absence of a copper co-catalyst. The reaction is carried out with pyrrolidine as the base in water at 120 °C.

  本文介绍了2-溴-1-苯基茚烯与苯基乙炔或丙炔醇的交叉偶联反应。该反应使用钯催化剂和三苯基膦，在无铜共催化剂的情况下进行。反应在120℃水溶液中以吡咯烷为碱催化剂进行。
• PROCESS TO MAKE HIGHLY SUBSTITUTED INDENES USING METAL SLAT CATALYSTS
  申请人：ROSOCHA Gregory

  公开号：US20150274617A1

  公开（公告）日：2015-10-01

  The present invention is a process to make 1-aryl-2-bromo substituted indenes and 1-phenyl-2-bromo substituted indenes that can have different functional groups present around the indene ring and/or the aromatic and/or phenyl ring. The indenes are made using the corresponding 1,2-biaryl-gem-dibromocyclopropane and/or 1,2-biphenyl-gem-dibromocyclopropanes and/or 1-aryl-2-phenyl-gem-dibromocyclopropanes using a metal salts, a solvent, low temperatures.
• THE SYNTHESIS OF TETRAHYDROISOQUINOLINES FROM 2-METHYL-1-PHENYL SUBSTITUTED INDENES
  申请人：ROSOCHA Gregory

  公开号：US20150284332A1

  公开（公告）日：2015-10-08

  A procedure for the synthesis of tetrahydroisoquinolines from 2-methyl-1-phenyl substituted indene is described. The process involves the use of osmium tetroxide to cleave the indene double bond forming the keto aldehyde product, which is then combined with a substituted amine forming the substituted isoquinoline. Isoquinolines can be useful as industrial products in the chemical, agrochemical, oil and gas industry, as well as useful as medicaments in the pharmaceutical industry.
• Synthesis of 2-bromo-1-aryl-1H-indenes via a Ag(I) promoted domino 2π-electrocyclic ring-opening/4π-electrocyclization reaction of 1,2-diaryl substituted gem-dibromocyclopropanes
  作者：Gregory Rosocha、Robert A. Batey

  DOI：10.1016/j.tet.2013.07.086

  日期：2013.10

  2-Bromo-1-aryl substituted indenes can be synthesized from 1,2-diaryl substituted gem-dibromocyclopropanes via a domino reaction sequence. The cascade reaction involves silver(I) promoted ionization and 2 pi-disrotatory electrocyclic ring-opening, followed by a 4 pi-conrotatory electrocyclic ring closing reaction of the allylic carbocation intermediate. Reaction conditions utilize silver tetrafluoroborate (AgBF4) in dichloroethane at 65 degrees C. Selectivity effects for the electrocyclization were also studied. The 2-bromoindenes can be further functionalized using cross-coupling reactions, such as the Suzuki-Miyaura protocol. The alkene it-bond of the indenes can also be isomerized to give the thermodynamically more stable 2-bromo-3-aryl-1H-indene isomers using triethylamine in dichloromethane at room temperature. (C) 2013 Published by Elsevier Ltd.