(4S)-4,5-dihydro-2-(2',4'-dihydroxyphenyl)-4-methyloxazole | 169171-37-3

• 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-methyloxazole
• 英文别名: 4-[(4S)-4-methyl-4,5-dihydro-1,3-oxazol-2-yl]benzene-1,3-diol
• CAS: 169171-37-3
• 化学式: C₁₀H₁₁NO₃
• 分子量: 193.202
• InChiKey: GCSIBTNGMOYOMH-LURJTMIESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.1
• 重原子数：
  14
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  62
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  3,4,5-tris(dodecanyloxy)benzoyl chloride 、 (4S)-4,5-dihydro-2-(2',4'-dihydroxyphenyl)-4-methyloxazole 在 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 24.0h， 以81%的产率得到(4S)-4,5-dihydro-4-methyl-2-{4'-[3'',4'',5''-tris(dodecyloxy)benzoyloxy]-2'-hydroxyphenyl}oxazole
  参考文献：
  名称：

  Chiral hexacatenar metallomesogens: supramolecular organization versus steric demand of chiral cores

  摘要：

  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。

  DOI：

  10.1039/b109487d
• 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-methyloxazole
  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

• Supramolecular Helical Stacking of Metallomesogens Derived from Enantiopure and Racemic Polycatenar Oxazolines
  作者：Joaquín Barberá、Emma Cavero、Matthias Lehmann、José-Luis Serrano、Teresa Sierra、Jesús T. Vázquez

  DOI：10.1021/ja0294313

  日期：2003.4.1

  which show columnar organization in the liquid crystalline state. To ensure the formation of chiral mesophases, these complexes bear stereogenic centers in the rigid coordination environment of the metal. X-ray and circular dichroism experiments have revealed that chirality transfer does indeed take place from the chiral molecule to the columnar liquid crystal organization. This chiral columnar organization

  本报告承担了对超分子化学普遍感兴趣的挑战：实现具有受控结构的螺旋组织。为了实现这一目标，我们考虑了使用旨在组织成柱状中间相的分子来诱导超分子手性的可能性。使用恶唑啉衍生的配体和金属配位作为工具来制备具有类囊泡结构的分子，其在液晶状态下显示柱状组织。为了确保手性中间相的形成，这些配合物在金属的刚性配位环境中具有立体中心。X 射线和圆二色性实验表明，手性转移确实发生从手性分子到柱状液晶组织。这种手性柱状组织表现为一个螺旋，由一堆分子组成，这些分子沿着柱子相互旋转，同时保持它们的平均平面彼此平行。事实上，已经得出结论，当分子相对于沿柱的相邻分子旋转时，这些多链分子的堆积必须更有效。此外，已发现在外消旋混合物的中间相和由外消旋配体制备的非对映异构体的混合物中存在相同类型的螺旋超组织。在这种情况下，建议发生光学异构体的分离以产生两种类型的螺旋（右手和左手）。