4-nonyloxyphenylacetylene | 79887-20-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: 4-nonyloxyphenylacetylene
• 英文别名: 1-Ethynyl-4-(nonyloxy)benzene；1-ethynyl-4-nonoxybenzene
• CAS: 79887-20-0
• 化学式: C₁₇H₂₄O
• 分子量: 244.377
• InChiKey: ZBLVEBNMFNZERM-UHFFFAOYSA-N

物化性质

• 沸点：
  338.4±25.0 °C(Predicted)
• 密度：
  0.93±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  6.2
• 重原子数：
  18
• 可旋转键数：
  10
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.53
• 拓扑面积：
  9.2
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  4-nonyloxyphenylacetylene 在 tin(ll) chloride 作用下， 以 乙醇 、 水 、 溶剂黄146 为溶剂， 反应 2.0h， 生成 1-[(4-nonyloxyphenyl)ethynyl]-4-(phenylethynyl)benzene
  参考文献：
  名称：

  A simple “palladium-free” synthesis of phenyleneethynylene-based molecular materials revisited

  摘要：

  对位醌的两个羰基受到乙酰阴离子的亲核攻击，很容易生成相应的二元醇。随后用氯化亚锡还原可得到许多有用的化合物，包括 1,4-双[（三甲基硅基）乙炔基]苯、1,4-双[（三甲基硅基）乙炔基]萘和 9,10-双[（三甲基硅基）乙炔基]蒽。不同乙酰阴离子的顺序攻击和还原为获得不同取代的化合物提供了有用的途径，其中包括 1-[(4-壬氧基苯基)乙炔基]-4-(苯基乙炔基)苯，这是一种新型发光液晶材料。

  DOI：

  10.1039/b502950c
• 作为产物：
  描述：

  1-溴壬烷 在 bis-triphenylphosphine-palladium(II) chloride 、 copper(l) iodide potassium carbonate 作用下， 以 三乙胺 、 丙酮 为溶剂， 反应 54.0h， 生成 4-nonyloxyphenylacetylene
  参考文献：
  名称：

  A simple “palladium-free” synthesis of phenyleneethynylene-based molecular materials revisited

  摘要：

  对位醌的两个羰基受到乙酰阴离子的亲核攻击，很容易生成相应的二元醇。随后用氯化亚锡还原可得到许多有用的化合物，包括 1,4-双[（三甲基硅基）乙炔基]苯、1,4-双[（三甲基硅基）乙炔基]萘和 9,10-双[（三甲基硅基）乙炔基]蒽。不同乙酰阴离子的顺序攻击和还原为获得不同取代的化合物提供了有用的途径，其中包括 1-[(4-壬氧基苯基)乙炔基]-4-(苯基乙炔基)苯，这是一种新型发光液晶材料。

  DOI：

  10.1039/b502950c

文献信息

• Chiral Tolans: A New Family of Ferroelectric Liquid Crystals. Synthesis and Mesomorphic Properties
  作者：Koji Seto、Hiroshi Shimojitosho、Hideyuki Imazaki、Hiroshi Matsubara、Shigetoshi Takahashi

  DOI：10.1246/bcsj.63.1020

  日期：1990.4

  chiral alkyl group, synthesized by a palladium-catalyzed coupling reaction, provide a new series of liquid crystalline materials which form chiral smectic C (SmC*) phases exhibiting ferroelectric properties. Mesomorphic properties of the compounds composed of three aromatic rings is strongly affected by the position of an acetylenic linkage and the direction of an ester linking unit. The effect of variations

  通过钯催化偶联反应合成的具有手性烷基的二苯乙炔同系物提供了一系列新的液晶材料，其形成具有铁电性质的手性近晶 C (SmC*) 相。由三个芳环组成的化合物的介晶性质受炔键位置和酯键单元方向的强烈影响。已经系统地研究了末端链长的变化对近晶 A (SmA) 和 SmC* 两个和三个芳环系统的热稳定性的影响。
• Liquid crystal compounds and compositions
  申请人：SANYO CHEMICAL INDUSTRIES, LTD.

  公开号：EP0500210A2

  公开（公告）日：1992-08-26

  Smectic C liquid crystal compounds, represented by the following formula (1) or (2) are disclosed. wherein R1 and R2 are C1-18 alkyl groups; A is a cyclic group, such as substituted or unsubstituted 1,4-phenylene group, X is direct bond, O or C-C ; Z is -C≡C- or -CH2CH2-; one of A1 and A2 is 1,4-phenylene group and the other is 2,3-difluoro-1,4-phenylene group ; and p is 0 or 1. These compounds can provide ferroelectric liquid crystal composition of low viscosity, and are useful as a component giving negative dielectric anisotropy and enlarging a temperature range showing smectic C phase.

  液晶化合物Smectic C，其化学式如下（1）或（2）所示。其中，R1和R2为C1-18烷基基团；A为环状基团，如取代或未取代的1,4-苯基基团；X为直接键，O或C-C；Z为-C≡C-或-CH2CH2-；A1和A2中的一个为1,4-苯基基团，另一个为2,3-二氟-1,4-苯基基团；p为0或1。这些化合物可以提供低粘度的铁电液晶组合物，并且可作为给出负介电各向异性并扩大显示Smectic C相的温度范围的组分。
• Synthesis and Mesomorphic Properties of Tolane-Based Fluorinated Liquid Crystals with an Acrylate Linkage
  作者：Ximin Chen、Yuehai Shen、Jianxun Wen

  DOI：10.1080/15421406.2010.504638

  日期：2010.10.14

  Six series of tolane-based fluorinated liquid crystals containing an acrylate linker were synthesized and their mesomorphic properties were characterized. The compounds generally exhibit SmA and N phases in wide temperature ranges. The introduction of acrylate linkers increases the clearing points by 20 degrees C-30 degrees C and suppresses the formation of higher ordered monotropic SmB phases. para-Fluorination is favorable for the mesophase stability, whereas meta-fluorination is not. The introduction of a 2,3,5,6-tetrafluorophenylene group decreases the clearing points and also suppresses the formation of the monotropic SmB phase.
• Synthesis and Mesomorphic Properties of Some Fluoro-Substituted Benzoates
  作者：Y. G. Yang、G. Tang、Z. Gong、J. X. Wen

  DOI：10.1080/10587250008024803

  日期：2000.8.1

  Several series of fluoro-substituted benzoate liquid crystals have been synthesized. The results showed that the SmA phase is enhanced with the increasing of the degree of fluoro-substitution on the para- and meta-postion of the terminal phenyl groups. And the molecules which have same molecular structural formula show nearly the same melting points. It is also discussed about the effect of the eater bond's direction on the mesomorphic properties.
• Synthesis and Mesomorphic Properties of Some Fluorinated Benzoate Liquid Crystals
  作者：Y. G. Yang、H. Chen、G. Tang、J. X. Wen

  DOI：10.1080/10587250210534

  日期：2002.1.1

  Three series of [4-(4'-n-alkyloxyphenyl)acetylenyl]-2,6-difluorophenyl fluorinated benezoates and one series of fluorinated benzoates with 2,3,5,6-tetrafluorophenylene group and semi-perfluorocarbon chain have been synthesized. Their phase transition temperatures have been measured by texture observation in a polarizing microscope and confirmed by DSC. For the series without fluorocarbon chains, increasing the quantity of fluorosubstituents on the terminal phenyl groups decreased nematic stability (TN-1), but the breadth of the SmA phase range was increased. Lateral fluorosubstitution in the central group lowered the nematic stability (TN-1) and decreased the breadth of the SmA phase range. The series with semiperfluorocarbon chains were more likely to form SmA phases than the series with hydrogencarbon chains, and with the increasing of fluorosubstituents quantity on the terminal phenyl groups nematic and SmA stability (T(N-)1 and TSmA-N) were both decreased.