9,9-双(2-乙基己基)芴 | 367524-07-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 芴
• 中文名称: 9,9-双(2-乙基己基)芴
• 英文名称: 9,9-Bis(rac-2-ethylhexyl)fluorene
• 英文别名: 9,9-bis(2-ethylhexyl)-9H-fluorene；9,9-bis(2-ethylhexyl)fluorene
• CAS: 367524-07-0
• 化学式: C₂₉H₄₂
• 分子量: 390.652
• InChiKey: YJUVFJKHTNWDNU-UHFFFAOYSA-N

物化性质

• 沸点：
  490.6±15.0 °C(Predicted)
• 密度：
  0.928±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  11.4
• 重原子数：
  29
• 可旋转键数：
  12
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.59
• 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：

  9,9-双(2-乙基己基)芴 在 硝酸 、 溶剂黄146 作用下， 以51.2%的产率得到2,7-dinitro-9,9-bis(2-ethylhexyl)fluorene
  参考文献：
  名称：

  2,3,6,7-Tetraamino-9,9-bis(2-ethylhexyl)fluorene: New Multifunctional Monomer for Soluble Ladder-Conjugated Molecules and Polymers

  摘要：

  2,3,6,7-Tetraamino-9,9-bis(2-ethylhexyl)fluorene (TABEF), as a new multifunctional monomer for ladder-type conjugated molecules and polymers, was efficiently synthesized via a six-step procedure with an overall yield of 30%. Two isomeric ladder compounds based on TABEF building blocks were also synthesized and preliminarily studied.

  DOI：

  10.1021/ol801081w
• 作为产物：
  描述：

  溴代异辛烷 、 芴 在 potassium tert-butylate 作用下， 以 四氢呋喃 为溶剂， 反应 0.83h， 以94%的产率得到9,9-双(2-乙基己基)芴
  参考文献：
  名称：

  芳烃与烷基卤化物的SN2烷基化后处理技术：旨在大规模合成软π分子材料的构建块

  摘要：

  通过用碱和硼化合物（硼氢化钠或 9-硼双环 [3.3.1] 壬烷）顺序后处理，可以有效去除芳族化合物 SN2 烷基化反应产物中未反应的卤代烷和副产物烯烃污染物，然后在硅胶。这些处理允许大规模纯化各种烷基化芳烃，从而有助于开发软 π 共轭材料，例如用于半导体聚合物的单体或烷基化 π 功能液体。

  DOI：

  10.1246/bcsj.20180075

文献信息

• Facile C−H Alkylation in Water: Enabling Defect-Free Materials for Optoelectronic Devices
  作者：Gunin Saikia、Parameswar K. Iyer

  DOI：10.1021/jo100028d

  日期：2010.4.16

  the alkylation of fluorene achieved via direct C−H alkylation under aqueous conditions is reported, wherein the formation of fluorenone is inhibited, resulting in the exclusive formation of the desired dialkyl-substituted fluorene monomer. As a proof of concept, this method has also been successfully extended to perform N-alkylation of carbazole, diphenylamine, and N,N-dialkylation of aniline in high

  报道了在水性条件下通过直接CH烷基化实现的芴烷基化的简便方法，其中抑制了芴酮的形成，导致仅形成所需的二烷基取代的芴单体。作为概念证明，该方法也已成功地扩展为以高收率进行咔唑，二苯胺的N-烷基化和苯胺的N，N-二烷基化。
• Preferential Oxidative Addition in Suzuki Cross-Coupling Reactions Across One Fluorene Unit
  作者：Sven K. Weber、Frank Galbrecht、Ullrich Scherf

  DOI：10.1021/ol061476b

  日期：2006.8.1

  The Suzuki-type cross-coupling reaction of 2,7-dihalofluorenes with 1 equiv of arylboronic acid and Pd-2(dba)(3)/P(t-Bu-3) as a catalyst system is investigated. The exclusive formation of the diarylated coupling product demonstrates that "preferential oxidative addition" is also applicable to fluorene monomers due to a controlled intramolecular motion of the regenerated Pd(0) catalyst across the "large" distance between the 2- and the 7-position of one fluorene monomer.
• Posttreatment Technique for S_N2 Alkylation of Aromatics with Alkyl Halides: Aiming toward Large-Scale Synthesis of Building Blocks for Soft π-Molecular Materials
  作者：Ken Okamoto、Fengniu Lu、Takashi Nakanishi

  DOI：10.1246/bcsj.20180075

  日期：2018.8.15

  byproduct olefin contaminants in products of SN2 alkylation reactions of aromatic compounds can be efficiently removed by sequential posttreatments with a base and a boron compound (sodium borohydride or 9-borabicyclo[3.3.1]nonane), followed by column chromatography on silica gel. These treatments permit large-scale purification of various alkylated aromatics, thereby assisting in the development of soft

  通过用碱和硼化合物（硼氢化钠或 9-硼双环 [3.3.1] 壬烷）顺序后处理，可以有效去除芳族化合物 SN2 烷基化反应产物中未反应的卤代烷和副产物烯烃污染物，然后在硅胶。这些处理允许大规模纯化各种烷基化芳烃，从而有助于开发软 π 共轭材料，例如用于半导体聚合物的单体或烷基化 π 功能液体。
• 2,3,6,7-Tetraamino-9,9-bis(2-ethylhexyl)fluorene: New Multifunctional Monomer for Soluble Ladder-Conjugated Molecules and Polymers
  作者：Xichuan Li、Yi Xiao、Xuhong Qian

  DOI：10.1021/ol801081w

  日期：2008.7.3

  2,3,6,7-Tetraamino-9,9-bis(2-ethylhexyl)fluorene (TABEF), as a new multifunctional monomer for ladder-type conjugated molecules and polymers, was efficiently synthesized via a six-step procedure with an overall yield of 30%. Two isomeric ladder compounds based on TABEF building blocks were also synthesized and preliminarily studied.