1-(2,3-dideoxy-β-D-erythro-hexanopyranosyl)-4-(methoxymethoxy)benzene | 651035-82-4

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 1-(2,3-dideoxy-β-D-erythro-hexanopyranosyl)-4-(methoxymethoxy)benzene
• 英文别名: (2R,3S,6R)-2-(hydroxymethyl)-6-[4-(methoxymethoxy)phenyl]oxan-3-ol
• CAS: 651035-82-4
• 化学式: C₁₄H₂₀O₅
• 分子量: 268.31
• InChiKey: MQGREMGFENPZEZ-BFHYXJOUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.3
• 重原子数：
  19
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.57
• 拓扑面积：
  68.2
• 氢给体数：
  2
• 氢受体数：
  5

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-(methoxymethoxy)benzene 以 甲苯 为溶剂， 45.0 ℃ 、6.0 kPa 条件下， 以66%的产率得到(1S,6R,8R)-3-(4-hexyloxyphenyl)-8-(4-(methoxymethoxy)phenyl)-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-溴-4-(甲氧基甲氧基)苯 在 [Rh(COD)(1,4-bis(diphenylphosphino)butane)]ClO₄ 四丁基氟化铵 、 氢气 、 magnesium 作用下， 以 四氢呋喃 、 乙醇 为溶剂， 反应 53.0h， 生成 1-(2,3-dideoxy-β-D-erythro-hexanopyranosyl)-4-(methoxymethoxy)benzene
  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