3,6-dibromo-9-isopropylcarbazole | 133950-36-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 3,6-dibromo-9-isopropylcarbazole
• 英文别名: 3,6-dibromo-N-isopropylcarbazole；3,6-Dibromo-9-isopropyl-9H-carbazole；3,6-dibromo-9-propan-2-ylcarbazole
• CAS: 133950-36-4
• 化学式: C₁₅H₁₃Br₂N
• 分子量: 367.083
• InChiKey: SCJWIJDHNIWXFZ-UHFFFAOYSA-N

物化性质

• 熔点：
  127-128 °C(Solvent: Ethanol)
• 沸点：
  443.6±38.0 °C(predicted)
• 密度：
  1.64±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.4
• 重原子数：
  18
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.2
• 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：

  3,6-dibromo-9-isopropylcarbazole 在 bis-triphenylphosphine-palladium(II) chloride 、 N-碘代丁二酰亚胺 、 copper(l) iodide 、 silver nitrate 、 三乙胺 、 potassium hydroxide 作用下， 以 四氢呋喃 、 甲醇 、 丙酮 为溶剂， 反应 48.0h， 生成 3,6-bis(iodoethynyl)-9-isopropylcarbazole
  参考文献：
  名称：

  Preorganization in a Cleft-Type Anion Receptor Featuring Iodo-1,2,3-Triazoles As Halogen Bond Donors

  摘要：

  Preorganization via intramolecular hydrogen bonds was applied in a cleft-type receptor by exploiting the excellent halogen bond donor ability as well as hydrogen bond acceptor function of iodo-1,2,3-triazoles. As investigated by isothermal calorimetric titrations, the restriction of conformational freedom causes an enhanced entropic contribution resulting in a strongly increased binding affinity. This efficient way to improve the binding strength of 5-halo-1,2,3-triazoles paves the way for applications of new charge-neutral halogen bond donors in solution.

  DOI：

  10.1021/acs.orglett.5b02760
• 作为产物：
  描述：

  咔唑 在 N-溴代丁二酰亚胺(NBS) 、 四丁基溴化铵 、 potassium hydroxide 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 、 丙酮 为溶剂， 反应 4.0h， 生成 3,6-dibromo-9-isopropylcarbazole
  参考文献：
  名称：

  用于设计反式共轭常规硅杂化材料 的新型苯乙烯基-N-异丙基-9 H-咔唑的合成†

  摘要：

  提出了一种有效的合成和表征的几种新的，立体控制的方法被单乙烯基硅烷官能化的共轭苯乙烯基咔唑化合物。在氢化钌配合物4和5的存在下，在甲硅烷基化偶联中成功地检测了所有N-有机衍生物。此外，还生产了一类新型的亚乙烯基-亚芳基线性低聚材料，其主链具有1,4-双（二甲基乙烯基甲硅烷基）萘。两种反应都非常有效地进行，在立体和区域选择性上进行，从而使人们可以获得具有高分离产率的E-异构体衍生物。

  DOI：

  10.1039/c6ob01560c

文献信息

• A convenient synthesis of 3,6-substituted carbazoles via nickel catalyzed cross-coupling
  作者：Minnie Park、Jason R. Buck、Carmelo J. Rizzo

  DOI：10.1016/s0040-4020(98)00786-8

  日期：1998.10

  Alkyl, vinyl and aryl substituted carbazoles at the 3- and 6-positions are prepared in high yield from the corresponding 3,6-dibromocarbazole via nickel catalyzed coupling with Grignard reagents (Corriu-Kumada coupling).

  经由镍与格氏试剂的偶联（Corriu-Kumada偶联），由相应的3,6-二溴咔唑高产率地制备3-位和6-位烷基，乙烯基和芳基取代的咔唑。
• Ni(COD)2 coupling of 3,6-dibromocarbazoles as a route to all-carbazole shape persistent macrocycles
  作者：Leah S. Coumont、Jonathan G.C. Veinot

  DOI：10.1016/j.tetlet.2015.08.048

  日期：2015.10

  The number of applications for carbon-based materials has experienced tremendous growth over the last decade arising from their low toxicity, straight-forward chemical modification, and interesting electronic properties. Among these materials, self-assembled structures based on shape persistent macrocycles are perhaps the most exciting as they offer a means to prepare a wide range of morphologies through reversible assembly of these molecular precursors. In this letter, we report on the preparation of a novel family of all-carbazole shape persistent macrocycles through the simple single-step reaction of the corresponding 3,6-dibromocarbazoles over Ni(COD)(2). The resultant macrocycles display optical properties characteristic of the parent N-alkyl polycarbazoles, with quantum yields ranging from 11% up to 21% suggesting that certain substituents induce the formation of highly emissive aggregates, which could potentially provide a mechanism for the preparation of functional self-assembled nanomaterials. (C) 2015 Elsevier Ltd. All rights reserved.
• Stereoselective synthesis and luminescence properties of novel trans-regular N-alkylcarbazolylene–silylene–vinylene polymers
  作者：Monika Ludwiczak、Mariusz Majchrzak、Małgorzata Bayda、Bronisław Marciniak、Maciej Kubicki、Bogdan Marciniec

  DOI：10.1016/j.jorganchem.2013.11.022

  日期：2014.1

  Novel trans-stereoregular silylene-carbazolylene-vinylene derivatives (13-15) were synthesized via silylative coupling reaction of 3,6-bis(dimethylvinylsilyl)-N-alkylcarbazole (7-9) catalyzed by ruthenium-hydride complex RuHCl(CO)(PCy3)(2) (1). All products were isolated, fully characterized by spectroscopic methods and GPC analyses and their absorption and fluorescence properties were determined. (C) 2013 Elsevier B. V. All rights reserved.
• COPOLYMER, ORGANIC SOLAR CELL USING THE SAME AND MANUFACTURING METHOD THEREOF
  申请人：Kim Jinseok

  公开号：US20130056073A1

  公开（公告）日：2013-03-07

  Disclosed herein are a 3,6-carbazole-containing copolymer, an organic solar cell comprising the copolymer in an organic material layer including a photoactive layer, and a method for fabricating the organic solar cell.
• Preorganization in a Cleft-Type Anion Receptor Featuring Iodo-1,2,3-Triazoles As Halogen Bond Donors
  作者：Ronny Tepper、Benjamin Schulze、Helmar Görls、Peter Bellstedt、Michael Jäger、Ulrich S. Schubert

  DOI：10.1021/acs.orglett.5b02760

  日期：2015.12.4

  Preorganization via intramolecular hydrogen bonds was applied in a cleft-type receptor by exploiting the excellent halogen bond donor ability as well as hydrogen bond acceptor function of iodo-1,2,3-triazoles. As investigated by isothermal calorimetric titrations, the restriction of conformational freedom causes an enhanced entropic contribution resulting in a strongly increased binding affinity. This efficient way to improve the binding strength of 5-halo-1,2,3-triazoles paves the way for applications of new charge-neutral halogen bond donors in solution.