2-(4-hydroxyphenyl)-5-octyloxypyrimidin | 104539-91-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 酚类
• 英文名称: 2-(4-hydroxyphenyl)-5-octyloxypyrimidin
• 英文别名: 2-(4-hydroxyphenyl)-5-octyloxypyrimidine；5-n-octyloxy-2-(4-hydroxyphenyl)-pyrimidine；4-(5-n-octyloxypyrimidin-2-yl)phenol；5-octyloxy-2-(p-hydroxyphenyl)pyrimidine；2-(4-hydroxy)phenyl-5-n-octyloxypyrimidine；5-octyloxy-2-(4-hydroxyphenyl)pyrimidine；4-(5-octyloxypyrimidine-2-yl)phenol；4-[5-(Octyloxy)pyrimidin-2(1H)-ylidene]cyclohexa-2,5-dien-1-one；4-(5-octoxypyrimidin-2-yl)phenol
• CAS: 104539-91-5
• 化学式: C₁₈H₂₄N₂O₂
• 分子量: 300.401
• InChiKey: OKGMOHVZKYWVHL-UHFFFAOYSA-N

物化性质

• 熔点：
  127-128 °C(Solv: dichloromethane (75-09-2); hexane (110-54-3))
• 沸点：
  386.4±34.0 °C(Predicted)
• 密度：
  1.076±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.9
• 重原子数：
  22
• 可旋转键数：
  9
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.44
• 拓扑面积：
  55.2
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2-(4-hydroxyphenyl)-5-octyloxypyrimidin 在 potassium tert-butylate 作用下， 以 叔丁醇 为溶剂， 生成 (3R,5S)-3-Butyl-5-[4-(5-octyloxy-pyrimidin-2-yl)-phenoxymethyl]-dihydro-furan-2-one
  参考文献：
  名称：

  Sakaguchi, Kazuhiko; Shiomi, Yutaka; Kitamura, Tohru, Chemistry Letters, 1991, # 7, p. 1109 - 1112

  摘要：

  DOI：
• 作为产物：
  描述：

  (E)-2-(dimethylamino)-3-octoxyprop-2-enal 、 N,N-二甲基甲酰胺 生成 2-(4-hydroxyphenyl)-5-octyloxypyrimidin
  参考文献：
  名称：

  OBA, KADZUMASA;MAIUNAGA, XITOSI

  摘要：

  DOI：

文献信息

• Synthesis and Liquid Crystalline Properties of 5-Alkyl-1,4-dioxane-2-carboxylic­ Esters
  作者：Manfred Braun、Birgit Spieker、Antje Hahn、Volkmar Vill

  DOI：10.1055/s-2002-34390

  日期：——

  The first route to 5-alkyl substituted and purely trans-configurated 1,4-dioxanecarboxylic acids 3 is described. The mesogenic properties of the esters 17 and 20, which are derived from the acids 3 and esters 19 (prepared from the hemiacetal 8a), are studied and compared. An enantioselective route to 1,4-dioxanecarboxylic acid 3a is explained, and takes advantage of the stereoselective addition of the bromolithioalkene 11b to heptanal.

  描述了制备5-烷基取代和纯反式构型1,4-二氧杂环己烷羧酸3的第一条路线。研究并比较了源自酸3的酯17和源自半缩醛8a制备的酯19得到的酯20的液晶性质。阐述了制备1,4-二氧杂环己烷羧酸3a的手性选择性路线，并利用了溴锂烯烃11b对庚醛的立体选择性加成。
• Nickel- and Palladium-Catalyzed Cross-Coupling Reactions at the Bridgehead of Bicyclo[1.1.1]pentane Derivatives - A Convenient Access to Liquid Crystalline Compounds Containing Bicyclo[1.1.1]pentane Moieties
  作者：Matthias Messner、Sergei I. Kozhushkov、Armin de Meijere

  DOI：10.1002/1099-0690(200004)2000:7<1137::aid-ejoc1137>3.0.co;2-2

  日期：2000.4

  Pd(PPh3)4, or PdCl2(dppf) catalysis to give a number of 1,3-disubstituted bicyclo[1.1.1]pentyl derivatives 17, 20, and 23, several of which exhibit liquid crystalline properties, in moderate to very good yields. The coupling products 20ca, 23ab, 23ae, 23ff, and 23fg have been further transformed to yield bicyclo[1.1.1]pentyl derivatives 32, 24ab, 24ae, 27ff, and 27fg, respectively, bearing alkynyl, cyano

  有机碘化物 7a-s 在 [1.1.1] 推进烷 (2) 上的自由基加成反应，然后是卤素-锂交换和与氯化锌的金属转移，以及将格利雅试剂添加到 2，提供了各种 3-取代双环[1.1.1]pentyl-1-magnesium (14) 和-zinc (19) 衍生物。后者在 NiCl2dppe、Pd(PPh3)4 或 PdCl2(dppf) 催化下与各种烯基、芳基和联芳基卤化物和三氟甲磺酸酯偶联，得到许多 1,3-二取代的双环 [1.1.1] 戊基衍生物 17 、20和23，其中一些表现出液晶性质，产率中等至非常好。偶联产物 20ca、23ab、23ae、23ff 和 23fg 已进一步转化为双环 [1.1.1] 戊基衍生物 32、24ab、24ae、27ff 和 27fg，分别带有炔基、氰基和/或烯基.
• Axial chiral allenylacetates as novel ferroelectric liquid crystals
  作者：Ralph Lunkwitz、Carsten Tschierske、Arne Langhoff、Frank Gießelmann、Peter Zugenmaier

  DOI：10.1039/a701032j

  日期：——

  Liquid crystalline alkane-3,4-dienoates (allenylacetates) have been synthesized. Most compounds incorporate a heterocyclic 1,3,4-thiadiazole ring or a pyrimidine ring as a constituent of the rigid core. These axial chiral allene derivatives were at first obtained as racemic mixtures. Some of them were also synthesized in enantiomerically enriched form by enantioselective synthesis. The compounds were investigated by polarizing microscopy and by differential scanning calorimetry. The three-ring compounds exhibit broad regions of smectic C-phases. The optically active three-ring compounds show broad S c *-phases with moderate values of spontaneous polarization.

  液晶烷烃-3,4-二烯酸盐（烯基乙酸盐）已被合成。大多数化合物的刚性核心都包含一个杂环 1,3,4-噻二唑环或一个嘧啶环。这些轴向手性烯衍生物最初是以外消旋混合物的形式获得的。其中一些还通过对映体选择性合成获得了对映体富集形式。这些化合物通过偏光显微镜和差示扫描量热法进行了研究。三环化合物呈现出宽广的胶状 C 相区域。具有光学活性的三环化合物显示出宽广的 S c * 相，自发极化值适中。
• Siloxane-terminated phenylpyrimidine liquid crystal hosts
  作者：Li Li、Christopher D. Jones、Jakob Magolan、Robert P. Lemieux

  DOI：10.1039/b700972k

  日期：——

  We report the synthesis and characterization of trisiloxane-terminated liquid crystals with 2-phenylpyrimidine cores that form partially bilayered SmA and SmC phases. Variable temperature measurements of smectic layer spacings by powder X-ray diffraction combined with measurements of optical tilt angles and observations of birefringence changes by polarized optical microscopy reveal that the trisiloxane end-group causes the SmA–SmC transition of these compounds to be more ‘de Vries-like’ when compared to a non-siloxane analogue. One such compound, 2-(4-(11-(1,1,1,3,3,5,5-heptamethyltrisiloxanyl)undecyloxy)phenyl)-5-(1-chlorooctyloxy)pyrimidine (3), is characterized by a maximum layer shrinkage of only 1.6% and may be considered a bona fide de Vries material.

  我们报告了以三硅氧烷为端基、以 2-苯基嘧啶为核心、形成部分双层 SmA 和 SmC 相的液晶的合成和表征。通过粉末 X 射线衍射法对 Smectic 层间距的变温测量、光学倾斜角的测量以及偏光光学显微镜对双折射变化的观察发现，与非硅氧烷类似物相比，三硅氧烷端基使这些化合物的 SmA-SmC 转变更加 "类似德弗里斯"。其中一种化合物是 2-(4-(11-(1,1,1,3,3,5,5-庚甲基三硅氧烷基)十一烷氧基)苯基)-5-(1-氯辛氧基)嘧啶 (3)，其最大层收缩率仅为 1.6%，可视为真正的 de Vries 材料。
• Process for controlling cone tilt angle in mixtures of smectic liquid
  申请人：Minnesota Mining and Manufacturing Company

  公开号：US05928562A1

  公开（公告）日：1999-07-27

  A process for controlling the cone tilt angle of a tilted smectic liquid crystal composition comprises the step of combining (a) at least one liquid crystal composition comprising at least one smectic or latent smectic liquid crystal compound comprising (i) an aliphatic fluorocarbon terminal portion comprising a terminal fluoroalkyl or fluoroether group and an alkylene group having at least two carbon atoms and containing at least one catenary ether oxygen atom, (ii) an aliphatic hydrocarbon terminal portion, and (iii) a central core connecting the terminal portions; and (b) at least one liquid crystal composition comprising at least one smectic or latent smectic liquid crystal compound; with the provisos that at least one of the compositions (a) and (b) comprises at least one chiral liquid crystal compound and that the combining of compositions (a) and (b) provides an optically active, tilted chiral smectic liquid crystal composition. The process enables control of cone tilt angle and thereby control of the brightness characteristics of liquid crystal display devices.

  一种用于控制倾斜相液晶组合物锥倾角的方法包括以下步骤：将（a）至少一种包含至少一种含有至少一种脂肪氟碳末端部分的倾斜相或潜在倾斜相液晶化合物的液晶组合物与（i）末端氟烷基或氟醚基团和至少含有两个碳原子的烷基团并且含有至少一个链状醚氧原子的烷基团，（ii）脂肪烃末端部分和（iii）连接末端部分的中心核心；以及（b）至少一种包含至少一种倾斜相或潜在倾斜相液晶化合物的液晶组合物相结合的步骤；但要求至少其中一种组合物（a）和（b）包含至少一种手性液晶化合物，并且组合物（a）和（b）的结合提供了一种光学活性的、倾斜的手性相液晶组合物。该方法使得能够控制锥倾角，从而控制液晶显示设备的亮度特性。