(R)-(+)-2-[4-(benzyloxy)phenyloxy]propionic acid | 79130-11-3

• 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: (R)-(+)-2-[4-(benzyloxy)phenyloxy]propionic acid
• 英文别名: (R)-2-(4-benzyloxyphenyloxy)propionic acid；(2R)-2-(4-phenylmethoxyphenoxy)propanoic acid
• CAS: 79130-11-3
• 化学式: C₁₆H₁₆O₄
• 分子量: 272.301
• InChiKey: ATPBADOREFXKFS-GFCCVEGCSA-N

物化性质

• 沸点：
  440.2±25.0 °C(Predicted)
• 密度：
  1.204±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  20
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.19
• 拓扑面积：
  55.8
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (R)-(+)-2-[4-(benzyloxy)phenyloxy]propionic acid 在 palladium on activated charcoal 4-二甲氨基吡啶 、 氢气 、 N,N'-二环己基碳二亚胺 作用下， 以 1,4-二氧六环 、 二氯甲烷 为溶剂， 反应 24.0h， 生成 (+)-7-(3-fluoro-4-benzyloxybenzoyloxy)-2-naphthyl (R)-2-[4-(3-fluoro-4-benzyloxybenzoyloxy)phenyloxy]propionate
  参考文献：
  名称：

  Liquid crystalline properties of unsymmetrical bent-core compounds containing chiral moieties

  摘要：

  报告了含有手性分子的新型非对称弯曲核化合物的合成、表征和介形性质。这些化合物以 3-羟基苯甲酸或 2,7-二羟基萘为中心单元。手性基团或作为连接基团加入到弯曲核心结构中，或附加在末端位置。我们研究了手性基团的位置对介形性质的影响。在末端链中含有手性基团（辛烷-2-醇）的弯曲核化合物表现出随着温度的降低，从手性钙钛矿相（如 SmC*、SmC*γ）直接过渡到具有二维晶格的极性香蕉相（ColobPA*）。为了证明这一相序，我们合成了末端链上带有外消旋辛烷-2-醇基团的相应化合物。初步观察和研究结果与手性化合物进行了比较。在 X 射线和电场实验的基础上，还讨论了这种不寻常相序的可能解释以及 ColobPA* (SmSPA*) 相的模型。

  DOI：

  10.1039/b419479a
• 作为产物：
  描述：

  methyl (2R)-2-(4-phenylmethoxyphenoxy)propanoate 在 水 、 sodium hydroxide 作用下， 以 乙醇 为溶剂， 生成 (R)-(+)-2-[4-(benzyloxy)phenyloxy]propionic acid
  参考文献：
  名称：

  Mesomorphism Behavior of Two Series of Chiral Compounds with Semiperfluorocarbon Chains

  摘要：

  Thermotropic liquid crystals with fluorocarbon chains have attracted much attention, because they are feasible to form smectic phases. Herein, two series of chiral compounds with semiperfluorocarbon chains were designed and synthesized. These compounds were characterized by IR, H-1 NMR, F-19 NMR, mass spectroscopy, and elemental analysis. Phase transition behavior was investigated by differential scanning calorimetry and polarized optical microscopy. Members of the two-ring series do not exhibit liquid crystalline phases. However, the three-ring analogues exhibit an enantiotropic SmA phase. When the length of alkyl chains is sufficient, an enantiotropic SmB phase is also identified.

  DOI：

  10.1080/15421406.2012.674466

文献信息

• Synthesis and mesomorphic properties of chiral liquid crystal dimers containing lactate units
  作者：S. Senthil、D. Srividhya、S. Manjunathan、S. Thirumaran、S.-L. Wu

  DOI：10.1016/j.molstruc.2007.07.022

  日期：2008.4

  Abstract A series of symmetrical chiral ferroelectric liquid crystal dimers viz., alkyl bis(R)-2-[4-(4′-decyloxyphenyl)benzoyloxyphenoxy]propionates}, ABDBP-n (n = 6–10), containing lactate units were synthesized and characterized. The length of the methylene spacer was increased from 6 to 10 in between the two chiral carbons located at the inner side of dimer. All the synthesized dimers exhibited

  摘要 一系列对称的手性铁电液晶二聚体，即烷基双(R)-2-[4-(4'-癸氧基苯基)苯甲酰氧基苯氧基]丙酸酯}，ABDBP-n (n = 6-10)，含有乳酸单元被合成和表征。在位于二聚体内侧的两个手性碳之间，亚甲基间隔基的长度从 6 增加到 10。所有合成的二聚体通过显示 N*、SmA*、SmC* 和 SmX*（未识别的）中间相序列表现出多态性。通过偏光显微镜和差示扫描量热测量确定中间相和它们相应的转变温度。SmC* 相中这些二聚体的电光开关研究显示出铁电双稳态开关特性，最大自发极化约为 60.74 nC cm-2。
• Terminal Effect of the Semi-fluorocarbon Chain on the Liquid Crystalline Behaviors of Some Compounds
  作者：Xiaoqing Wu、Yongmin Guo、Yi Li、Baozong Li、Yonggang Yang

  DOI：10.1080/15421406.2018.1539422

  日期：2018.5.3

  Two series of chiral compounds with semi-perfluorocarbon chains and alkoxy ones, nBP4F and nBP6F, are synthesized. Enantiotropic SmA phase is identified in all of these compounds. When the alkoxy chain length is short, enantiotropic SmB is also identified. When the alkoxy chain length is longer than 6 carbons, enantiotropic SmC* phase is formed. Their clearing points increase with increasing the perfluorocarbon chain length. Comparison of compounds with -CF3, -CHF2 and -CF2Cl groups at the terminals of the fluorocarbon chains, the clearing point sequence is -CHF2 < -CF2Cl < -CF3; and the melting point sequence is -CF3 < -CHF2 < -CF2Cl. Therefore, the compounds with semi-perfluorocarbon chains show the widest liquid crystalline temperature range. Moreover, the SmC* phase of the compounds with -CF3 at the terminals shows the highest thermostability.
• US5252695A
  申请人：——

  公开号：US5252695A

  公开（公告）日：1993-10-12
• Liquid crystalline properties of unsymmetrical bent-core compounds containing chiral moieties
  作者：R. Amaranatha Reddy、B. K. Sadashiva、U. Baumeister

  DOI：10.1039/b419479a

  日期：——

  The synthesis, characterization and mesomorphic properties of new unsymmetrical bent-core compounds containing chiral moieties are reported. These compounds have been derived from either 3-hydroxybenzoic acid or 2,7-dihydroxynaphthalene as the central unit. The chiral group is incorporated either within the bent-core structure as a linking group or is appended in the terminal position. The influence of the position of the chiral moiety on the mesomorphic properties has been investigated. The bent-core compounds containing a chiral group (octan-2-ol) in the terminal chain exhibit a direct transition from chiral calamitic phases such as SmC*, SmC*γ to a polar banana phase with a two-dimensional lattice (ColobPA*) on decreasing temperature. In order to prove this phase sequence, the corresponding compound with a racemic octan-2-ol group at the terminal chain has been synthesized. The preliminary observations and investigations are presented for comparison with the chiral compound. Possible explanations for this unusual phase sequence and the models for the ColobPA* (SmSPA*) phase are also discussed on the basis of X-ray and electric field experiments.

  报告了含有手性分子的新型非对称弯曲核化合物的合成、表征和介形性质。这些化合物以 3-羟基苯甲酸或 2,7-二羟基萘为中心单元。手性基团或作为连接基团加入到弯曲核心结构中，或附加在末端位置。我们研究了手性基团的位置对介形性质的影响。在末端链中含有手性基团（辛烷-2-醇）的弯曲核化合物表现出随着温度的降低，从手性钙钛矿相（如 SmC*、SmC*γ）直接过渡到具有二维晶格的极性香蕉相（ColobPA*）。为了证明这一相序，我们合成了末端链上带有外消旋辛烷-2-醇基团的相应化合物。初步观察和研究结果与手性化合物进行了比较。在 X 射线和电场实验的基础上，还讨论了这种不寻常相序的可能解释以及 ColobPA* (SmSPA*) 相的模型。
• Mesomorphism Behavior of Two Series of Chiral Compounds with Semiperfluorocarbon Chains
  作者：Jie Li、Nan Zhao、Yi Li、Baozong Li、Yonggang Yang

  DOI：10.1080/15421406.2012.674466

  日期：2012.8.22

  Thermotropic liquid crystals with fluorocarbon chains have attracted much attention, because they are feasible to form smectic phases. Herein, two series of chiral compounds with semiperfluorocarbon chains were designed and synthesized. These compounds were characterized by IR, H-1 NMR, F-19 NMR, mass spectroscopy, and elemental analysis. Phase transition behavior was investigated by differential scanning calorimetry and polarized optical microscopy. Members of the two-ring series do not exhibit liquid crystalline phases. However, the three-ring analogues exhibit an enantiotropic SmA phase. When the length of alkyl chains is sufficient, an enantiotropic SmB phase is also identified.