Trimethylsilyltetra-O-trimethylsilylchinat | 364628-95-5

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: Trimethylsilyltetra-O-trimethylsilylchinat
• CAS: 364628-95-5
• 化学式: C₂₂H₅₂O₆Si₅
• 分子量: 553.079
• InChiKey: DBCLHKSGLLGXOV-VMBXEPDQSA-N

物化性质

• 沸点：
  442.6±45.0 °C(Predicted)
• 密度：
  0.95±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  6.41
• 重原子数：
  33.0
• 可旋转键数：
  10.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.95
• 拓扑面积：
  63.22
• 氢给体数：
  0.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  Trimethylsilyltetra-O-trimethylsilylchinat 在 吡啶 、 盐酸 、 4-二甲氨基吡啶 、 三氟甲磺酸三甲基硅酯 、 2,2-二甲氧基丙烷 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 5.0h， 生成 (-)-5-咖啡酰奎宁酸
  参考文献：
  名称：

  First Efficient Synthesis of Chlorogenic Acid

  摘要：

  The first efficient synthesis of chlorogenic acid (1) was achieved in four steps (three purifications) from quinic acid (2). The overall yield was 65%. The key intermediate was quinic acid bisacetonide (6), selectively prepared by a modified kinetic acetalization protocol. Esterification of 6 with caffeic acid chloride (3) afforded ester 12. Cleavage of all the protecting groups of 12 was accomplished in one step under acidic conditions. The progress of the hydrolysis was monitored by MALDI-MS.

  DOI：

  10.1002/1099-0690(200103)2001:6<1137::aid-ejoc1137>3.0.co;2-2
• 作为产物：
  描述：

  三甲基氯硅烷 、 右旋奎宁酸 在 三乙胺 作用下， 反应 4.5h， 以95%的产率得到Trimethylsilyltetra-O-trimethylsilylchinat
  参考文献：
  名称：

  First Efficient Synthesis of Chlorogenic Acid

  摘要：

  The first efficient synthesis of chlorogenic acid (1) was achieved in four steps (three purifications) from quinic acid (2). The overall yield was 65%. The key intermediate was quinic acid bisacetonide (6), selectively prepared by a modified kinetic acetalization protocol. Esterification of 6 with caffeic acid chloride (3) afforded ester 12. Cleavage of all the protecting groups of 12 was accomplished in one step under acidic conditions. The progress of the hydrolysis was monitored by MALDI-MS.

  DOI：

  10.1002/1099-0690(200103)2001:6<1137::aid-ejoc1137>3.0.co;2-2

文献信息

• First Efficient Syntheses of 1-, 4-, and 5-Caffeoylquinic Acid
  作者：Michael Sefkow、Alexandra Kelling、Uwe Schilde

  DOI：10.1002/1099-0690(200107)2001:14<2735::aid-ejoc2735>3.0.co;2-i

  日期：2001.7
• Scholz-Boettcher, Barbara M.; Ernst, Ludger; Maier, Hans Gerhard, Liebigs Annalen der Chemie, 1991, # 10, p. 1029 - 1036
  作者：Scholz-Boettcher, Barbara M.、Ernst, Ludger、Maier, Hans Gerhard

  DOI：——

  日期：——
• First Efficient Synthesis of Chlorogenic Acid
  作者：Michael Sefkow

  DOI：10.1002/1099-0690(200103)2001:6<1137::aid-ejoc1137>3.0.co;2-2

  日期：2001.3

  The first efficient synthesis of chlorogenic acid (1) was achieved in four steps (three purifications) from quinic acid (2). The overall yield was 65%. The key intermediate was quinic acid bisacetonide (6), selectively prepared by a modified kinetic acetalization protocol. Esterification of 6 with caffeic acid chloride (3) afforded ester 12. Cleavage of all the protecting groups of 12 was accomplished in one step under acidic conditions. The progress of the hydrolysis was monitored by MALDI-MS.