1-(2,3-dideoxy-β-D-erythro-hexanopyranosyl)-4-hydroxybenzene | 651035-71-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 酚类
• 英文名称: 1-(2,3-dideoxy-β-D-erythro-hexanopyranosyl)-4-hydroxybenzene
• 英文别名: (2R,3S,6R)-2-(hydroxymethyl)-6-(4-hydroxyphenyl)oxan-3-ol
• CAS: 651035-71-1
• 化学式: C₁₂H₁₆O₄
• 分子量: 224.257
• InChiKey: DXWBOCZESVUITJ-QJPTWQEYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.1
• 重原子数：
  16
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  69.9
• 氢给体数：
  3
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  4-甲氧基苯硼酸 、 1-(2,3-dideoxy-β-D-erythro-hexanopyranosyl)-4-hydroxybenzene 以 甲苯 为溶剂， 45.0 ℃ 、6.0 kPa 条件下， 以50%的产率得到(1S,6R,8R)-8-(4-hydroxyphenyl)-3-(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-hydroxybenzene 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-hydroxybenzene
  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