1-溴-6-(辛-1-炔基)芘 | 273219-32-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 芘
• 中文名称: 1-溴-6-(辛-1-炔基)芘
• 英文名称: 1-Bromo-6-(oct-1-ynyl)pyrene
• 英文别名: 1-bromo-6-(1-octynyl)pyrene；1-Bromo-6-oct-1-ynylpyrene
• CAS: 273219-32-2
• 化学式: C₂₄H₂₁Br
• 分子量: 389.335
• InChiKey: JBSCITRLQWLQFI-UHFFFAOYSA-N

物化性质

• 沸点：
  526.7±23.0 °C(Predicted)
• 密度：
  1.33±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  9.1
• 重原子数：
  25
• 可旋转键数：
  5
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.25
• 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：

  1-溴-6-(辛-1-炔基)芘 在 platinum(IV) oxide bis-triphenylphosphine-palladium(II) chloride 、 copper(l) iodide 、 氢气 、 4-甲基苯磺酸吡啶 作用下， 以 四氢呋喃 、 乙醇 、 二氯甲烷 为溶剂， 生成 3-[6-(1-octyl)-1-pyrenyl]propan-1-ol
  参考文献：
  名称：

  Electron Transport across Vesicle Bilayers Sensitized by Pyrenes: Design and Syntheses of Unsymmetrically Substituted Bifunctional Pyrenes Acting as Excellent Sensitizers

  摘要：

  嵌入囊泡壁中的芘衍生物有助于穿过囊泡双层的内部水池中的电子供体向外部水溶液中的电子受体的电子传递。尽管这种敏化能力非常依赖于芘环上的取代基团。新设计的芘衍生物，同时具有通过亚甲基链连接的亲水基团和较长的疏水链，发现其能作为优秀的敏化剂。

  DOI：

  10.1246/cl.2003.68
• 作为产物：
  描述：

  1-辛炔 、 1,6-二溴芘 在 bis-triphenylphosphine-palladium(II) chloride 、 copper(l) iodide 吗啉 作用下， 反应 10.0h， 以58%的产率得到1-溴-6-(辛-1-炔基)芘
  参考文献：
  名称：

  Synthesis of a novel tweezers-type host aiming at chiral discrimination by circular dichroism spectroscopy †

  摘要：

  为了在主-客体系统中利用络合诱导的圆二色性（ICD）开发一种手性鉴别方法，合成了新型镊子型主体 1。紫外-可见光谱和荧光发射研究证实，宿主 1 与具有光学活性的 N,N′-二甲基-反式-1,2-二氨基环己烷 16 形成了 1∶1 的络合物，并且随着络合物浓度的增加，CD 光谱被诱导。(S,S)-16诱导的科顿效应的符号与(R,R)-16诱导的科顿效应的符号相反，这表明络合时 1 的对映选择性异构体的形成可导致通过 CD 确定客体的手性。另一方面，1 与手性单胺 17 复配后的 ICD 表明，直到宿主与两个分子的 17 复配，才会诱导出 1 的轴向手性。

  DOI：

  10.1039/a909468g

文献信息

• Pyrene-sensitized electron transport across vesicle bilayers: dependence of transport efficiency on pyrene substituents
  作者：Tadashi Mizushima、Asako Yoshida、Akitomo Harada、Yu Yoneda、Tomiaki Minatani、Shigeru Murata

  DOI：10.1039/b609507k

  日期：——

  (Asc-) in the inner waterpool to methylviologen (MV2+) in the outer aqueous solution was driven by the irradiation of pyrene derivatives embedded in the vesicle bilayers. The initial rate of MV2+ reduction is dependent on the substituent group of the pyrenyl ring; a hydrophilic functional group linked with the pyrenyl ring by a short methylene chain acts as a sensitizer for the electron transport. Mechanistic

  通过嵌入在囊泡双层中的pyr衍生物的驱动，从囊泡双层中的内能电子传输从内部水池中的抗坏血酸盐（Asc-）到外部水溶液中的甲基紫精（MV2 +）。MV2 +还原的初始速率取决于the环的取代基。通过亚甲基短链与the环相连的亲水性官能团充当电子传输的敏化剂。使用（1-吡啶基）链烷酸（1a-c）作为敏化剂的机理研究表明，电子传输主要是由Asc-对the的单重激发态进行还原性猝灭而引发的，并通过涉及电子之间交换的机理进行located位于囊泡双层的内部和外部界面。
• Synthesis of a novel tweezers-type host aiming at chiral discrimination by circular dichroism spectroscopy †
  作者：Shigeyuki Yagi、Hirokazu Kitayama、Toru Takagishi

  DOI：10.1039/a909468g

  日期：——

  In order to develop a methodology for chiral discrimination by utilizing complexation-induced circular dichroism (ICD) in host–guest systems, the novel tweezers-type host 1 was synthesized. From UV-VIS and fluorescence emission studies, it was confirmed that the host 1 formed a 1∶1 complex with optically active N,N′-dimethyl-trans-1,2-diaminocyclohexane 16, and the CD spectrum was induced as the concentration of the complex increased. The sign of the Cotton effect induced by (S,S)-16 was opposite to that induced by (R,R)-16, indicating that enantioselective formation of the atropisomer of 1 upon complexation leads to determination of the chirality of the guest by CD. On the other hand, the ICD of 1 upon complexation with the chiral monoamine 17 implied that the axial chirality of 1 was not induced until the host complexed two molecules of 17.

  为了在主-客体系统中利用络合诱导的圆二色性（ICD）开发一种手性鉴别方法，合成了新型镊子型主体 1。紫外-可见光谱和荧光发射研究证实，宿主 1 与具有光学活性的 N,N′-二甲基-反式-1,2-二氨基环己烷 16 形成了 1∶1 的络合物，并且随着络合物浓度的增加，CD 光谱被诱导。(S,S)-16诱导的科顿效应的符号与(R,R)-16诱导的科顿效应的符号相反，这表明络合时 1 的对映选择性异构体的形成可导致通过 CD 确定客体的手性。另一方面，1 与手性单胺 17 复配后的 ICD 表明，直到宿主与两个分子的 17 复配，才会诱导出 1 的轴向手性。
• Electron Transport across Vesicle Bilayers Sensitized by Pyrenes: Design and Syntheses of Unsymmetrically Substituted Bifunctional Pyrenes Acting as Excellent Sensitizers
  作者：Asako Yoshida、Akitomo Harada、Tadashi Mizushima、Shigeru Murata

  DOI：10.1246/cl.2003.68

  日期：2003.1

  An electron transport from an electron donor entrapped into inner waterpool to an electron acceptor in outer aqueous solution across vesicle bilayers was sensitized by pyrene derivatives incorporated in the vesicle walls, although the sensitizer ability was very dependent on the substituent group on the pyrenyl ring. The newly designed pyrenes having both a hydrophilic group linked by short methylene chain and a hydrophobic long alkyl group were found to act as excellent sensitizers.

  嵌入囊泡壁中的芘衍生物有助于穿过囊泡双层的内部水池中的电子供体向外部水溶液中的电子受体的电子传递。尽管这种敏化能力非常依赖于芘环上的取代基团。新设计的芘衍生物，同时具有通过亚甲基链连接的亲水基团和较长的疏水链，发现其能作为优秀的敏化剂。
• Amphiphilic pyrenecarboxylic acids: incorporation into vesicle membrane and ability as sensitizer for electron transport reactions
  作者：Ryo Sasaki、Yuki Nako、Shigeru Murata

  DOI：10.1016/j.tet.2009.07.033

  日期：2009.9

  The novel pyrenecarboxylic acids 1-3 having a single or double hydrophobic alkyl chain were synthesized, and their photophysical properties were investigated in solutions and vesicle membranes. In analogy with parent 1-pyrenecarboxylic acid, the absorption and fluorescence spectra of 1-3 were changed with the H+ concentration. The amphiphilic pyrenecarboxylic acids 1-3 had good solubility in the vesicle membranes, and acted as an excellent sensitizer for the electron transport from an electron donor in the inner waterpool of the vesicle to an electron acceptor in the outer aqueous phase across vesicle membranes. (C) 2009 Elsevier Ltd. All rights reserved.