1-[4,6-di-O-tert-butyl(dimethyl)silyl-2,3-dideoxy-β-D-erythro-hex-2-enopyranosyl]-4-(dimethylamino)benzene | 651035-52-8

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: 1-[4,6-di-O-tert-butyl(dimethyl)silyl-2,3-dideoxy-β-D-erythro-hex-2-enopyranosyl]-4-(dimethylamino)benzene
• 英文别名: 4-[(2R,3S,6R)-3-[tert-butyl(dimethyl)silyl]oxy-2-[[tert-butyl(dimethyl)silyl]oxymethyl]-3,6-dihydro-2H-pyran-6-yl]-N,N-dimethylaniline
• CAS: 651035-52-8
• 化学式: C₂₆H₄₇NO₃Si₂
• 分子量: 477.835
• InChiKey: RRPIDOKMTBSVIH-TZRRMPRUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.16
• 重原子数：
  32.0
• 可旋转键数：
  7.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.69
• 拓扑面积：
  30.93
• 氢给体数：
  0.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  1-[4,6-di-O-tert-butyl(dimethyl)silyl-2,3-dideoxy-β-D-erythro-hex-2-enopyranosyl]-4-(dimethylamino)benzene 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 、 甲苯 为溶剂， 20.0~45.0 ℃ 、6.0 kPa 条件下， 反应 29.0h， 生成 (1S,6R,8R)-8-(4-(dimethylamino)phenyl)-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：

  4-溴-N,N-二甲基苯胺 、 p-tert-butylphenyl 4,6-di-O-(tert-butyldimethylsilyl)-2,3-dideoxy-α-D-erythro-hex-2-enopyranoside 在 magnesium 、 1,2-双(二苯基膦)乙烷氯化镍 作用下， 以 四氢呋喃 为溶剂， 反应 24.0h， 以80%的产率得到1-[4,6-di-O-tert-butyl(dimethyl)silyl-2,3-dideoxy-β-D-erythro-hex-2-enopyranosyl]-4-(dimethylamino)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