1,4-Bis[(S)-2-methylbutoxy]benzene | 191032-93-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: 1,4-Bis[(S)-2-methylbutoxy]benzene
• 英文别名: 1,4-bis[2(S)-methylbutoxy]benzene
• CAS: 191032-93-6
• 化学式: C₁₆H₂₆O₂
• 分子量: 250.381
• InChiKey: BBECQEXYNOTUPX-KBPBESRZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.54
• 重原子数：
  18.0
• 可旋转键数：
  8.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.62
• 拓扑面积：
  18.46
• 氢给体数：
  0.0
• 氢受体数：
  2.0

反应信息

• 作为反应物：
  描述：

  1,4-Bis[(S)-2-methylbutoxy]benzene 在 溴 作用下， 以 二氯甲烷 为溶剂， 以77%的产率得到1,4-dibromo-2,5-bis((S)-2-methylbutoxy)benzene
  参考文献：
  名称：

  聚集态头尾结构聚（1,4-亚苯基）的高强度圆二色性

  摘要：

  使用镍-Chiraphos络合物作为催化剂可以合成多种具有手性侧链的聚(1,4-亚苯基)，并通过圆二色光谱的测量为其螺旋结构的相关性提供新的见解。

  DOI：

  10.1002/chem.202400706
• 作为产物：
  描述：

  (S)-2-甲基丁基对甲苯磺酸酯 、 对苯二酚 在 potassium hydroxide 作用下， 以1.62 g的产率得到1,4-Bis[(S)-2-methylbutoxy]benzene
  参考文献：
  名称：

  聚集态头尾结构聚（1,4-亚苯基）的高强度圆二色性

  摘要：

  使用镍-Chiraphos络合物作为催化剂可以合成多种具有手性侧链的聚(1,4-亚苯基)，并通过圆二色光谱的测量为其螺旋结构的相关性提供新的见解。

  DOI：

  10.1002/chem.202400706

文献信息

• Planar-Chiral Pillar[5]arene: Chiral Switches Induced by Multiexternal Stimulus of Temperature, Solvents, and Addition of Achiral Guest Molecule
  作者：Tomoki Ogoshi、Ryohei Shiga、Tada-aki Yamagishi、Yoshiaki Nakamoto

  DOI：10.1021/jo1021508

  日期：2011.1.21

  We synthesized chiral-substituents modified pillar[5]arene for the first time. The chiral-substituents modified pillar[5]arene showed planar chirality and interconversion between (pS) and (pR) forms took place quickly. The planar chirality was switched by temperature, solvents, and addition of achiral guest. As the measurement temperature increased, the diastereomeric excess was decreased. The diastereomeric

  我们首次合成了手性取代基修饰的支柱[5]芳烃。手性取代基修饰的支柱[5]芳烃表现出平面手性，并且（pS）和（pR）形式之间的相互转化很快发生。平面手性通过温度，溶剂和非手性客体的添加来切换。随着测量温度升高，非对映异构体过量减少。在低介电常数溶剂中，非对映异构体过量较高，而在高介电常数溶剂中，非对映异构体过量较低。非手性客人的增加导致负CD强度的增加。
• Dynamic‐to‐Static Planar Chirality Conversion in Pillar[5]arenes Regulated by Guest Solvents or Amplified by Crystallization
  作者：Keisuke Wada、Misaki Suzuki、Takahiro Kakuta、Tada‐aki Yamagishi、Shunsuke Ohtani、Shixin Fa、Kenichi Kato、Shigehisa Akine、Tomoki Ogoshi

  DOI：10.1002/anie.202217971

  日期：——

  The pR and pS forms of pillar[5]arene regulated by short- and long-chain guest solvents, respectively, were both diastereomerically memorized by introducing bulky groups through click reactions. The diastereomeric excess was also amplified by crystallization of the pillar[5]arene. The subsequent introduction of bulky groups yielded a pillar[5]arene with excellent diastereomeric excess (95 % de).

  pR和pS形式的柱 [5] 芳烃分别由短链和长链客体溶剂调节，都通过点击反应引入庞大的基团来实现非对映体记忆。柱 [5] 芳烃的结晶也放大了非对映体过量。随后引入庞大的基团产生了具有出色的非对映体过量 (95% de )的柱 [5] 芳烃 。
• Steering the Conformation and Chiroptical Properties of Poly(dithienopyrrole)s Substituted with Chiral OPV Side Chains.
  作者：Wouter Vanormelingen、Lesley Pandey、Mark Van der Auweraer、Thierry Verbiest、Guy Koeckelberghs

  DOI：10.1021/ma902762z

  日期：2010.3.9

  This manuscript discusses the conformation and chiroptical properties of poly(dithienopyrrole)s (PDTPs), Substituted with oligo(phenylenevinylene) (OPV) side chains and the influence of the substitution of the OPV moiety on these features. The OPV side chains were equipped with gallic acid moieties in order to promote the formation of a helical conformation in poor solvents. The polymers were prepared by Stille-couplings and characterized by GPC and NMR, UV-vis, CID, and emission spectroscopy. It was found that OPV-PDTPs, solely equipped with (chiral) alkyl groups at the terminal gallic acid group, show a very strong tendency to adopt a helical conformation, but no resolution or the mixture of helices and therefore no chiral expression. Additional substitution of the allows for a discrimination of the mixture of lielical senses. In this way, the OPV side chains can bechirally organized by the helical PDTP backbone. Substitution of the OPV in a-position, however, sterically excludes the possibility to adopt a helical conformation, but results in a lamellar supramolecular Structure in poor solvents. The macromolecular behavior is explained in terms of space confinement and sieric hindrance in the respective Structures.
• Constitutionally Asymmetric and Chiral [2]Pseudorotaxanes¹
  作者：Masumi Asakawa、Peter R. Ashton、Wayne Hayes、Henk M. Janssen、E. W. Meijer、Stephan Menzer、Dario Pasini、J. Fraser Stoddart、Andrew J. P. White、David J. Williams

  DOI：10.1021/ja970018i

  日期：1998.2.1

  The self-assembly and characterization of a range of chiral pseudorotaxanes has been explored using chiroptical methods. The syntheses of (i) constitutionally asymmetric acyclic hydroquinone-containing polyethers and (ii) optically active hydroquinone-containing acyclic polyethers, bearing pairs of methyl or isobutyl groups related to each other in a C-2-symmetric manner within the polyether backbone, are described. The combination of (i) the tetracationic cyclophane cyclobis(paraquat-p-phenylene) tetrakis(hexafluorophosphate), possessing a pi-electron deficient cavity, and (ii) the linear noncentrosymmetric acyclic polyethers produces [2]pseudorotaxanes that have been characterized by H-1 NMR, UV/vis and circular dichroism (CD) spectroscopies in solution and by X-ray crystallography in the solid state. The introduction of constitutional asymmetry or chirality gives rise to a number of different geometries for the [2]pseudorotaxanes in both the solution and solid states. in particular, CD-spectroscopic measurements on the optically active [2]pseudorotaxanes have shown that-depending on the positions of the C-2 symmetrically related chiral centers in the polyether chains with respect to the hydroquinone rings-the chirality present in the pi-electron rich threadrike guest can induce chirality that is associated with the supramolecular structure as a whole, resulting in a chiral charge-transfer transition involving not only the pi-donors in the chiral guests but also the pi-acceptors in the achiral host.
• Synthesis, Photophysical Properties, and Photovoltaic Devices of Oligo(<i>p</i>-phenylene vinylene)-fullerene Dyads
  作者：Emiel Peeters、Paul A. van Hal、Joop Knol、Christoph J. Brabec、N. Serdar Sariciftci、J. C. Hummelen、René A. J. Janssen

  DOI：10.1021/jp001717b

  日期：2000.11.1

  The synthesis of a homologous series of oligo(p,-phenylene vinylene)-fulleropyrrolidines (OPVn-C-60, n 1-4, where n is the number of phenyl rings) is described. The photophysical properties of these donor-acceptor dyads and the corresponding model compounds, alpha,omega -dimethyl-2,5-bis(2- (S)-methylbutoxy)-1,4-phenylene vinylene oligomers (OPVn, n = 2-4) and N-methylfulleropyrrolidine (MP-C-60), are studied as a function of the conjugation length in solvents of different polarity and as thin films. Fast singlet energy transfer occurs after photoexcitation of the OPVn moiety of the dyads toward the fullerene moiety in an apolar solvent. Photoexcitation of the dyads in a polar solvent results in electron transfer fur OPV3-C-60 and OPV4-C-60. and to some extent for OPV2-C-60, but not for OPV1-C-60 These results are compared to the results obtained for mixtures of OPVn and MP-C-60 in the same solvents. The solvent-dependent change in free energy for charge separation of the donor-acceptor systems is calculated from the Weller equation, and the rate constants for energy and electron transfer are derived from the fluorescence lifetime and quenching. The results show that in a polar solvent electron transfer in these dyads is likely to occur via a two-step process, that is, a very fast singlet energy transfer prior to charge separation. In thin solid films of OPV3-C-60 and OPV4-C-60, a long-lived charge-separated state is Termed after photoexcitation. The long lifetime in the film is attributed to the migration of charges to different molecules. A flexible photovoltaic device is prepared from OPV4-C-60.