1-(2,3-dideoxy-β-D-erythro-hexanopyranosyl)-4-methoxybenzene | 651035-76-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: 1-(2,3-dideoxy-β-D-erythro-hexanopyranosyl)-4-methoxybenzene
• 英文别名: (2R,3S,6R)-2-(hydroxymethyl)-6-(4-methoxyphenyl)oxan-3-ol
• CAS: 651035-76-6
• 化学式: C₁₃H₁₈O₄
• 分子量: 238.284
• InChiKey: YVKAEPGXAITBFX-YNEHKIRRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  17
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.54
• 拓扑面积：
  58.9
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  4-己氧基苯硼酸 、 1-(2,3-dideoxy-β-D-erythro-hexanopyranosyl)-4-methoxybenzene 以 甲苯 为溶剂， 45.0 ℃ 、6.0 kPa 条件下， 以60%的产率得到(1S,6R,8R)-3-(4-hexyloxyphenyl)-8-(4-methoxyphenyl)-2,4,7-trioxa-3-borabicyclo[4.4.0]decane
  参考文献：
  名称：

  Enantiopure Trioxadecalin Derived Liquid Crystals: Influence of the Nature of the Phenyl Substituent on the Mesogenic Properties

  摘要：

  Reaction of pseudo-glucal 1 with Grignard reagents derived from 1-bromo-4(trimethylsilyloxy)benzene, 1-bromo-4-methoxybenzene, 1-bromo-4-methoxymethoxybenzene, 1-bromo-4-dimethylaminobenzene, in the presence of a catalytic amount of NiCl2(dppe), gives the corresponding unsaturated beta-C-aryl glycosides 2. Desilylation and hydrogenation of 2 leads to beta-C-aryl glycosides 4, which can be used as chiral precursor compounds in the synthesis of chiral liquid crystals. Combination of 4 with arylaldehydes leads to compounds 5-7, whereas reaction with p-alkoxysubstituted phenylboronic acids gives the trioxaboradecalins 8-11. The mesogenic properties of these compounds are strongly influenced by the nature of the substituent on the phenyl ring in the molecule.

  DOI：

  10.1081/car-120026468
• 作为产物：
  描述：

  1-[4,6-di-O-tert-butyl(dimethyl)silyl-2,3-dideoxy-β-D-erythro-hex-2-enopyranosyl]-4-methoxybenzene 在 [Rh(COD)(1,4-bis(diphenylphosphino)butane)]ClO₄ 四丁基氟化铵 、 氢气 作用下， 以 四氢呋喃 、 乙醇 为溶剂， 反应 29.0h， 生成 1-(2,3-dideoxy-β-D-erythro-hexanopyranosyl)-4-methoxybenzene
  参考文献：
  名称：

  Enantiopure Trioxadecalin Derived Liquid Crystals: Influence of the Nature of the Phenyl Substituent on the Mesogenic Properties

  摘要：

  Reaction of pseudo-glucal 1 with Grignard reagents derived from 1-bromo-4(trimethylsilyloxy)benzene, 1-bromo-4-methoxybenzene, 1-bromo-4-methoxymethoxybenzene, 1-bromo-4-dimethylaminobenzene, in the presence of a catalytic amount of NiCl2(dppe), gives the corresponding unsaturated beta-C-aryl glycosides 2. Desilylation and hydrogenation of 2 leads to beta-C-aryl glycosides 4, which can be used as chiral precursor compounds in the synthesis of chiral liquid crystals. Combination of 4 with arylaldehydes leads to compounds 5-7, whereas reaction with p-alkoxysubstituted phenylboronic acids gives the trioxaboradecalins 8-11. The mesogenic properties of these compounds are strongly influenced by the nature of the substituent on the phenyl ring in the molecule.

  DOI：

  10.1081/car-120026468

文献信息

• Structural variation of liquid crystalline trioxadecalins
  作者：Volkmar Vill、Hanns-Walter Tunger、Markus von Minden

  DOI：10.1039/jm9960600739

  日期：——

  Synthesis and mesogenic properties of new liquid crystals bearing a chiral trioxadecalin system are described. Boron-containing three-ring systems with a lateral methoxy group show cholesteric, TGBA and smectic A phases. Molecules containing four or five rings show mostly smectic C* phases. The insertion of a triple bond leads to ferroelectric smectic C* phases, but compounds with a flexible spacer between the rings show only monotropic smectic A phases. Lateral fluorination of the aromatic rings leads, depending on the position of the fluorine, either to stabilised smectic phases with lower transition temperatures or to cholesteric phases with complete suppression of all smectic phases.

  本文描述了带有手性三氧杂萘烷体系的新型液晶的合成和介电性质。带有一个侧甲氧基的含硼三环系统显示出胆固醇相、TGBA 相和共晶 A 相。含有四环或五环的分子主要呈现出平滑的 C* 相。插入一个三键会导致铁电共晶 C* 相，但环间有柔性间隔的化合物只显示单向共晶 A 相。根据氟的位置，芳香环的侧向氟化会导致过渡温度较低的稳定共晶相或完全抑制所有共晶相的胆甾相。
• Carbohydrate-based liquid crystals: new compounds showing re-entrant TGBA and cholesteric phases and dopant-induced TGBA, SA and SC* phases
  作者：Volkmar Vill、Hanns-Walter Tunger

  DOI：10.1039/c39950001047

  日期：——

  Re-entrant TGBA and cholesteric phases are observed in a homologous series of pure chiral carbohydrate-based compounds, and contact preparation induces SA phases between cholesteric and nematic compounds as well as re-entrant and Sc* phases in two substances which in pure form only show cholesteric and SA phases.

  在纯手性碳水化合物基化合物的同源系列中观察到了再入相 TGBA 和胆甾相，接触制备法在胆甾相和向列化合物之间诱导出了 SA 相，并在两种纯物质中诱导出了再入相和 Sc* 相，而这两种物质在纯形式下只显示胆甾相和 SA 相。
• Sign inversion of the helical pitch in carbohydrate-based liquid crystals
  作者：Volkmar Vill、Hanns-Walter Tunger、Horst Stegemeyer、Karsten Diekmann

  DOI：10.1016/s0957-4166(00)80391-2

  日期：1994.12

  A four-step synthesis starting from tri-O-acetyl-D-glucal leads to chiral trioxadecalin compounds containing a cyano group. The mesogenic properties of a homologous series of liquid crystals are reported; for two derivatives a helix inversion of the cholesteric phase is observed.