2-bromo-1-phenyl-1H-indene | 88069-78-7

• 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-phenyl-1H-indene
• 英文别名: 2-Bromo-1-phenyl-1H-indene
• CAS: 88069-78-7
• 化学式: C₁₅H₁₁Br
• 分子量: 271.156
• InChiKey: PTUGNIQKAZYSQR-UHFFFAOYSA-N

物化性质

• 沸点：
  371.2±31.0 °C(Predicted)
• 密度：
  1.439±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.6
• 重原子数：
  16
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  0
• 氢给体数：
  0
• 氢受体数：
  0

反应信息

• 作为反应物：
  描述：

  2-bromo-1-phenyl-1H-indene 在 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 2.0h， 以85%的产率得到2-bromo-3-phenyl-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
• 作为产物：
  描述：

  二苯乙烯 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 21.5h， 生成 2-bromo-1-phenyl-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] PROCESS TO MAKE HIGHLY SUBSTITUTED INDENES USING METAL SLAT CATALYSTS<br/>[FR] PROCÉDÉ DE PRODUCTION D'INDÈNES FORTEMENT SUBSTITUÉS À L'AIDE DE CATALYSEURS DE TYPE SEL MÉTALLIQUE
  申请人：ROSOCHA GREGORY

  公开号：WO2014064477A1

  公开（公告）日：2014-05-01

  The present invention is a process to make l-aryl-2-bromo substituted indenes and l-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.

  本发明是一种制备具有不同官能团的1-芳基-2-溴代茚和1-苯基-2-溴代茚的过程，这些官能团可以存在于茚环和/或芳香环和/或苯环周围。使用相应的1,2-双芳基-双溴环丙烷和/或1,2-双苯基-双溴环丙烷和/或1-芳基-2-苯基-双溴环丙烷，利用金属盐、溶剂和低温制备茚烯。
• [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。
• [EN] THE SYNTHESIS OF TETRAHYDROISOQUINOLINES FROM 2-METHYL-1-PHENYL SUBSTITUTED INDENES<br/>[FR] SYNTHÈSE DE TÉTRAHYDROISOQUINOLINES À PARTIR D'INDÈNES SUBSTITUÉS PAR 2-MÉTHYL-1-PHÉNYLE
  申请人：ROSOCHA GREGORY

  公开号：WO2014064476A1

  公开（公告）日：2014-05-01

  A procedure for the synthesis of tetrahydroisoquinolines from 2-methyl-l -phenyl substituted indene is described. The process invovles 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.

  本文介绍了从2-甲基-1-苯基取代茚烯合成四氢异喹啉的过程。该过程涉及使用四氧化锇裂解茚烯双键，形成酮醛产物，然后与取代胺结合形成取代异喹啉。异喹啉可作为化学、农药、石油和天然气工业的工业产品，也可作为药物在制药工业中使用。
• FUNCTIONALIZED ALPHA-OLEFIN POLYMER, AS WELL AS CURED COMPOSITION AND CURED ARTICLE USING SAME
  申请人：IDEMITSU KOSAN CO., LTD.

  公开号：US20150252226A1

  公开（公告）日：2015-09-10

  A functionalized α-olefin polymer having an α-olefin polymer main chain and an alkoxysilyl group and satisfying the following (a) to (d): (a) The meso-pentad fraction [mmmm] is less than 20 mol %, or the meso-diad fraction [m] is less than 95 mol %. (b) The weight-average molecular weight (Mw) is from 1,000 to 500,000. (c) The alkoxysilyl group concentration in all the monomer units is from 0.01 to 50 mol %. (d) The α-olefin polymer is a propylene homopolymer, a 1-butene homopolymer or a propylene-1-butene copolymer.

  具有α-烯烃聚合物主链和烷氧基硅基团的功能化α-烯烃聚合物，满足以下条件（a）至（d）：（a）中间偏向分数[mmmm]小于20摩尔％，或中间二元分数[m]小于95摩尔％。 （b）重均分子量（Mw）为1,000至500,000。 （c）所有单体单位中的烷氧基硅基团浓度为0.01至50摩尔％。 （d）α-烯烃聚合物是丙烯同聚物，1-丁烯同聚物或丙烯-1-丁烯共聚物。
• FUNCTIONALIZED ALPHA-OLEFIN POLYMER, AS WELL AS CURED COMPOSITION AND CURED ARTICLE USING SAME
  申请人：Idemitsu Kosan Co., Ltd

  公开号：EP2899216A1

  公开（公告）日：2015-07-29

  A functionalized α-olefin polymer having an α-olefin polymer main chain and an alkoxysilyl group and satisfying the following (a) to (d): (a) The meso-pentad fraction [mmmm] is less than 20 mol%, or the meso-diad fraction [m] is less than 95 mol%. (b) The weight-average molecular weight (Mw) is from 1,000 to 500,000. (c) The alkoxysilyl group concentration in all the monomer units is from 0.01 to 50 mol%. (d) The α-olefin polymer is a propylene homopolymer, a 1-butene homopolymer or a propylene-1-butene copolymer.

  一种具有α-烯烃聚合物主链和烷氧基硅烷基团并满足以下(a)至(d)条件的官能化 α-烯烃聚合物： (a) 中五元组分[mmmm]小于 20 摩尔%，或中二元组分[m]小于 95 摩尔%。(b) 重量平均分子量（Mw）为 1,000 至 500,000。(c) 所有单体单元中的烷氧基硅烷基浓度为 0.01 至 50 摩尔%。(d) α-烯烃聚合物是丙烯均聚物、1-丁烯均聚物或丙烯-1-丁烯共聚物。