2,2,5-tribromoindan-1-one

• 分子结构分类: 有机化合物 - 苯类化合物 - 茚满类
• 英文名称: 2,2,5-tribromoindan-1-one
• 英文别名: 2,2,5-tribromoindanone；2,2,5-tribromo-3H-inden-1-one
• 化学式: C₉H₅Br₃O
• 分子量: 368.85
• InChiKey: PQHWZDFGJBSXJI-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  13
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  17.1
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  2,2,5-tribromoindan-1-one 反应 0.75h， 以22%的产率得到3,8,13-tribromo-diindeno[1,2-a;1',2'-c]fluorene-5,10,15-trione
  参考文献：
  名称：

  Synthesis, (Non)Linear Optical and Redox Properties of a Donor-Substituted Truxenone Derivative

  摘要：

  two-dimensional NLO chromophore (7) with three donor-substituted branches and truxenone as the central coupling unit was synthesised from tribromotruxenone by Stille coupling with N,N-di(4-methoxyphenyl)-4'-(tributylstannylethynyl)phenylamine. UV/visible spectroscopy and hyper-Rayleigh scattering measurements prove the truxenone moiety to be a far stronger electron acceptor than, for example, a nitro group. In addition, coupling of excited states leads to an enhanced quadratic hyperpolarisability of 7 compared with one-dimensional reference chromophores. The large redox-potential separation of about 400 mV of the three reductive waves in the cyclic voltammetry also indicates strong electronic coupling of the truxenone unit. Semiempirical computations at AMI-CI level were used to explain the strong coupling; these calculations also suggest a quartet high-spin state for the truxenone trianion. UV/visible spectroelectrochemical investigations of the oxidation and the first reduction of 7 show that both processes weaken the CT excitation so as to modulate the NLO properties.

  DOI：

  10.1002/(sici)1521-3765(19981102)4:11<2129::aid-chem2129>3.0.co;2-0
• 作为产物：
  描述：

  5-溴茚酮 在 溴 作用下， 以 氯仿 为溶剂， 反应 1.0h， 以83%的产率得到2,2,5-tribromoindan-1-one
  参考文献：
  名称：

  Synthesis, (Non)Linear Optical and Redox Properties of a Donor-Substituted Truxenone Derivative

  摘要：

  two-dimensional NLO chromophore (7) with three donor-substituted branches and truxenone as the central coupling unit was synthesised from tribromotruxenone by Stille coupling with N,N-di(4-methoxyphenyl)-4'-(tributylstannylethynyl)phenylamine. UV/visible spectroscopy and hyper-Rayleigh scattering measurements prove the truxenone moiety to be a far stronger electron acceptor than, for example, a nitro group. In addition, coupling of excited states leads to an enhanced quadratic hyperpolarisability of 7 compared with one-dimensional reference chromophores. The large redox-potential separation of about 400 mV of the three reductive waves in the cyclic voltammetry also indicates strong electronic coupling of the truxenone unit. Semiempirical computations at AMI-CI level were used to explain the strong coupling; these calculations also suggest a quartet high-spin state for the truxenone trianion. UV/visible spectroelectrochemical investigations of the oxidation and the first reduction of 7 show that both processes weaken the CT excitation so as to modulate the NLO properties.

  DOI：

  10.1002/(sici)1521-3765(19981102)4:11<2129::aid-chem2129>3.0.co;2-0

文献信息

• PPh₃·HBr–DMSO: A Reagent System for Diverse Chemoselective Transformations
  作者：Kanchan Mal、Amanpreet Kaur、Fazle Haque、Indrajit Das

  DOI：10.1021/acs.joc.5b00846

  日期：2015.6.19

  The broad applicability of the hitherto unexplored reagent combination PPh3 center dot HBr-DMSO is exemplified with multiple highly diverse one-step transformations to synthetically useful building blocks, such as flavones, 4H-thiochromen-4-ones, alpha-hydroxy ketones, 1,4-naphthoquinones (including vitamin K-3), 2-bromo-3-substituted-1H-1-indenones, 2-rnethylthio-1H-1-indenones, 3-butyne-1,2-dione, and 4-pentene-2,3-diones. The simple and mild reaction conditions make the reagent superior in terms of yield and substrate scope in comparison with the existing alternatives.
• Synthesis, (Non)Linear Optical and Redox Properties of a Donor-Substituted Truxenone Derivative
  作者：Christoph Lambert、Gilbert Nöll、Elmar Schmälzlin、Klaus Meerholz、Christoph Bräuchle

  DOI：10.1002/(sici)1521-3765(19981102)4:11<2129::aid-chem2129>3.0.co;2-0

  日期：1998.11.2

  two-dimensional NLO chromophore (7) with three donor-substituted branches and truxenone as the central coupling unit was synthesised from tribromotruxenone by Stille coupling with N,N-di(4-methoxyphenyl)-4'-(tributylstannylethynyl)phenylamine. UV/visible spectroscopy and hyper-Rayleigh scattering measurements prove the truxenone moiety to be a far stronger electron acceptor than, for example, a nitro group. In addition, coupling of excited states leads to an enhanced quadratic hyperpolarisability of 7 compared with one-dimensional reference chromophores. The large redox-potential separation of about 400 mV of the three reductive waves in the cyclic voltammetry also indicates strong electronic coupling of the truxenone unit. Semiempirical computations at AMI-CI level were used to explain the strong coupling; these calculations also suggest a quartet high-spin state for the truxenone trianion. UV/visible spectroelectrochemical investigations of the oxidation and the first reduction of 7 show that both processes weaken the CT excitation so as to modulate the NLO properties.

表征谱图