2-bromo-6-methyl-1-phenyl-1H-indene | 1454309-42-2

• 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-6-methyl-1-phenyl-1H-indene
• CAS: 1454309-42-2
• 化学式: C₁₆H₁₃Br
• 分子量: 285.183
• InChiKey: IXGJPVWCYRLFOR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.9
• 重原子数：
  17
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.12
• 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：

  4-methylstilbene 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 45.0h， 生成 2-bromo-6-methyl-1-phenyl-1H-indene 、 2-bromo-1-(p-tolyl)-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

• 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.