4-(2,3-dideoxy-β-D-erythro-hexanopyranosyl)biphenyl | 368452-31-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 4-(2,3-dideoxy-β-D-erythro-hexanopyranosyl)biphenyl
• 英文别名: (2R,3S,6R)-2-(hydroxymethyl)-6-(4-phenylphenyl)oxan-3-ol
• CAS: 368452-31-7
• 化学式: C₁₈H₂₀O₃
• 分子量: 284.355
• InChiKey: URWKSJKZNOGWDT-RCCFBDPRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  21
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  49.7
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  4-丁氧基苯硼酸 、 4-(2,3-dideoxy-β-D-erythro-hexanopyranosyl)biphenyl 以 甲苯 为溶剂， 45.0 ℃ 、6.0 kPa 条件下， 以69%的产率得到(1S,6R,8R)-8-biphenyl-3-(4'-butyloxyphenyl)-2,4,7-trioxa-3-borabicyclo[4.4.0]decane
  参考文献：
  名称：

  ENANTIOPURE TRIOXADECALIN DERIVED LIQUID CRYSTALS: INFLUENCE OF PHENYL SUBSTITUTION ON THE MESOGENIC PROPERTIES

  摘要：

  Nickel(0)-catalyzed reaction of pseudo-glucal 1 with Grignard reagents derived from bromobenzene and 1-bromo-4-phenylbenzene gives the corresponding beta -C-aryl glycosides 2. Desilylation and hydrogenation of 2 leads to saturated beta -C-aryl glycosides 4, which can be used as chiral intermediates in the synthesis of chiral liquid crystals. The combination with p-alkoxy-substituted benzaldehyde leads to compounds 5-6. Alternatively, reaction with p-alkoxy-substituted phenylboronic acids gives the bora analogues 7-9. The mesogenic properties of these compounds are strongly influenced by the presence of an additional phenyl ring in the molecule.

  DOI：

  10.1081/car-100104867
• 作为产物：
  描述：

  2-BIPHENYLMAGNESIUM BROMIDE 在 1,2-双(二苯基膦)乙烷氯化镍 、 [Rh(COD)(1,4-bis(diphenylphosphino)butane)]ClO₄ 四丁基氯化铵 、 氢气 作用下， 以 四氢呋喃 、 乙醇 为溶剂， 20.0 ℃ 、101.33 kPa 条件下， 反应 50.0h， 生成 4-(2,3-dideoxy-β-D-erythro-hexanopyranosyl)biphenyl
  参考文献：
  名称：

  ENANTIOPURE TRIOXADECALIN DERIVED LIQUID CRYSTALS: INFLUENCE OF PHENYL SUBSTITUTION ON THE MESOGENIC PROPERTIES

  摘要：

  Nickel(0)-catalyzed reaction of pseudo-glucal 1 with Grignard reagents derived from bromobenzene and 1-bromo-4-phenylbenzene gives the corresponding beta -C-aryl glycosides 2. Desilylation and hydrogenation of 2 leads to saturated beta -C-aryl glycosides 4, which can be used as chiral intermediates in the synthesis of chiral liquid crystals. The combination with p-alkoxy-substituted benzaldehyde leads to compounds 5-6. Alternatively, reaction with p-alkoxy-substituted phenylboronic acids gives the bora analogues 7-9. The mesogenic properties of these compounds are strongly influenced by the presence of an additional phenyl ring in the molecule.

  DOI：

  10.1081/car-100104867

文献信息

• ENANTIOPURE TRIOXADECALIN DERIVED LIQUID CRYSTALS: INFLUENCE OF PHENYL SUBSTITUTION ON THE MESOGENIC PROPERTIES
  作者：Bruno Bertini、Christophe Moineau、Denis Sinou、Volkmar Vill

  DOI：10.1081/car-100104867

  日期：2001.4.30

  Nickel(0)-catalyzed reaction of pseudo-glucal 1 with Grignard reagents derived from bromobenzene and 1-bromo-4-phenylbenzene gives the corresponding beta -C-aryl glycosides 2. Desilylation and hydrogenation of 2 leads to saturated beta -C-aryl glycosides 4, which can be used as chiral intermediates in the synthesis of chiral liquid crystals. The combination with p-alkoxy-substituted benzaldehyde leads to compounds 5-6. Alternatively, reaction with p-alkoxy-substituted phenylboronic acids gives the bora analogues 7-9. The mesogenic properties of these compounds are strongly influenced by the presence of an additional phenyl ring in the molecule.