(4S)-4,5-dihydro-2-(2',4'-dihydroxyphenyl)-4-<(S)-1-methylpropyl>oxazole | 169171-34-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 酚类
• 英文名称: (4S)-4,5-dihydro-2-(2',4'-dihydroxyphenyl)-4-<(S)-1-methylpropyl>oxazole
• CAS: 169171-34-0
• 化学式: C₁₃H₁₇NO₃
• 分子量: 235.283
• InChiKey: HIKZWMSCCHMBCH-GZMMTYOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.29
• 重原子数：
  17.0
• 可旋转键数：
  3.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.46
• 拓扑面积：
  62.05
• 氢给体数：
  2.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  1-碘癸烷 、 (4S)-4,5-dihydro-2-(2',4'-dihydroxyphenyl)-4-<(S)-1-methylpropyl>oxazole 在 氢氧化钾 作用下， 以 二甲基亚砜 为溶剂， 反应 17.0h， 以51%的产率得到(4S)-4,5-dihydro-2-(4'-decyloxy-2'-hydroxyphenyl)-4-<(S)-1-methylpropyl>oxazole
  参考文献：
  名称：

  Improving FLC Properties. Simplicity, Planarity, and Rigidity in New Chiral Oxazoline Derivatives

  摘要：

  In an attempt to develop new dopants for improved ferroelectric properties in liquid crystals, aryloxazolines have been chosen as chiral moieties. They were prepared in optically active form from (s)-beta-amino alcohols via a short stereospecific synthesis and incorporated into mesogenic systems. Mesogenic and ferroelectric properties of 11 compounds in five series of chiral oxazoline derivatives [I(OH), I(H), II(OH), II(H), and III(OH)] have been studied. In order to establish the relationship between the molecular structure and ferroelectric properties, an in-depth structural investigation of both H-bonded and non-H-bonded phenyloxazoline moieties was carried out (by means of semiempirical calculations-AM1-and spectroscopic studies-IR, UV and H-1 NMR). These studies have proved a planar structure for both types of structures, which should have a strong influence on ferroelectric properties. These properties have been evaluated in 10 mol % binary mixtures. The highest Ps values were measured for compounds of series I(OH) [P-s max(I(OH)a) = 16.7 nC/cm(2), P-s max(I(OH)b) = 13.2 nC/cm(2)] containing a hydrogen bond, which makes the chiral part of the molecule more rigid. Compound III(OH)a shows a wide SmC* phase range which supercools well below room temperature, and it has been studied as a ferroelectric liquid crystal in the pure state. The P-s max measured is appreciably high: 225 nC/cm(2). Its special thermal behavior (showing a glass transition at -28 degrees C) makes this compound very interesting from the point of view of practical applications and will be the target of further studies.

  DOI：

  10.1021/ja00137a003
• 作为产物：
  描述：

  2,4-二羟基苯甲醛肟 在 氢氧化钾 、 乙酸酐 、 zinc(II) chloride 作用下， 以 氯苯 为溶剂， 反应 21.0h， 生成 (4S)-4,5-dihydro-2-(2',4'-dihydroxyphenyl)-4-<(S)-1-methylpropyl>oxazole
  参考文献：
  名称：

  Improving FLC Properties. Simplicity, Planarity, and Rigidity in New Chiral Oxazoline Derivatives

  摘要：

  In an attempt to develop new dopants for improved ferroelectric properties in liquid crystals, aryloxazolines have been chosen as chiral moieties. They were prepared in optically active form from (s)-beta-amino alcohols via a short stereospecific synthesis and incorporated into mesogenic systems. Mesogenic and ferroelectric properties of 11 compounds in five series of chiral oxazoline derivatives [I(OH), I(H), II(OH), II(H), and III(OH)] have been studied. In order to establish the relationship between the molecular structure and ferroelectric properties, an in-depth structural investigation of both H-bonded and non-H-bonded phenyloxazoline moieties was carried out (by means of semiempirical calculations-AM1-and spectroscopic studies-IR, UV and H-1 NMR). These studies have proved a planar structure for both types of structures, which should have a strong influence on ferroelectric properties. These properties have been evaluated in 10 mol % binary mixtures. The highest Ps values were measured for compounds of series I(OH) [P-s max(I(OH)a) = 16.7 nC/cm(2), P-s max(I(OH)b) = 13.2 nC/cm(2)] containing a hydrogen bond, which makes the chiral part of the molecule more rigid. Compound III(OH)a shows a wide SmC* phase range which supercools well below room temperature, and it has been studied as a ferroelectric liquid crystal in the pure state. The P-s max measured is appreciably high: 225 nC/cm(2). Its special thermal behavior (showing a glass transition at -28 degrees C) makes this compound very interesting from the point of view of practical applications and will be the target of further studies.

  DOI：

  10.1021/ja00137a003

文献信息

• Chiral hexacatenar metallomesogens: supramolecular organization versus steric demand of chiral cores
  作者：Matthias Lehmann、Teresa Sierra、Joaquin Barberá、José Luis Serrano、Robert Parker

  DOI：10.1039/b109487d

  日期：2002.4.17

  Hexacatenar chiral oxazoline complexes were prepared in a stereospecific synthesis. Metals (Pd, Ni, Cu, Zn), lateral alkoxy chains (OC6H13, OC12H25), sterically demanding alkyl groups (CH3, C4H9) on the chiral rigid centre and the number of nuclei incorporated in the complex core (mononuclear, orthopalladated dinuclear) were varied in order to achieve supramolecular organization of the phasmid-like molecules in liquid crystal phases. Mesomorphic properties were not observed in neat materials, but phase diagrams of binary mixtures with TNF demonstrate that steric repulsion can be overcome by intercalation of the electron-acceptor TNF. In spite of the presence of six lateral chains, SmA phases were found exclusively. The structures of the SmA phases were found to have additional order with respect to SmA phases formed by calamitic molecules. Further examination of the complexes in host nematic materials demonstrated their use as chiral dopants to induce cholesteric LC phases.

  六手性噁唑啉络合物通过立体特异性合成制备。金属（Pd、Ni、Cu、Zn）、侧链烷氧基（OC6H13、OC12H25）、手性刚性中心上的空间位阻烷基（CH3、C4H9）以及络合物核心中结合的原子数（单核、正钯化双核）均有所不同，以实现液晶相中类相变分子超分子组织。在纯净材料中未观察到介形性质，但与TNF的二元混合物的相图表明，空间位阻可以通过电子受体TNF的插入来克服。尽管存在六个侧链，但只发现了SmA相。发现SmA相的结构与由钙质分子形成的SmA相相比具有更高的有序性。进一步研究显示，在主链性材料中，络合物可用作手性掺杂剂，诱导胆固醇液晶相。