praecoxin B | 113900-70-2

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 单宁
• 英文名称: praecoxin B
• 英文别名: pariin M；[(10R,13R,14R,15S)-3,4,5,11,20,21,22-heptahydroxy-8,17-dioxo-14-(3,4,5-trihydroxybenzoyl)oxy-9,12,16-trioxatetracyclo[16.4.0.02,7.010,15]docosa-1(22),2,4,6,18,20-hexaen-13-yl]methyl 3,4,5-trihydroxybenzoate
• CAS: 113900-70-2
• 化学式: C₃₄H₂₆O₂₂
• 分子量: 786.567
• InChiKey: TYNMNHMNJMTUEU-HTCCRONFSA-N

物化性质

• 沸点：
  1393.9±65.0 °C(Predicted)
• 密度：
  2.12±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.2
• 重原子数：
  56
• 可旋转键数：
  7
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  377
• 氢给体数：
  13
• 氢受体数：
  22

反应信息

• 作为反应物：
  描述：

  praecoxin B 在 单宁酶 作用下， 生成 2,3-(S)-hexahydroxydiphenoyl-D-glucose
  参考文献：
  名称：

  Praecoxin B,C,D and E, novel ellagitannins from Stachyurus praecox.

  摘要：

  从早春小水杉（Stachyurus praecox）中分离出了普雷香素C（6）、D（7）和E（8），这些是具有酯链的椰子单宁，以及普雷香素B（9），它是堇菜苷I（1）的异构体。

  DOI：

  10.1248/cpb.31.333
• 作为产物：
  描述：

  2,3-O-<(R)-2,2',3,3',4,4'-hexabenzyloxydiphenoyl>-4,6-di-O-(3,4,5-tri-O-benzylgalloyl)-D-glucopyranose 在 palladium on activated charcoal 氢气 作用下， 以 四氢呋喃 为溶剂， 反应 24.0h， 以83%的产率得到praecoxin B
  参考文献：
  名称：

  Synthesis of Enantiomerically Pure Unusual Ellagitannins 1,4,6-Tri-O-galloyl-2,3-(R)-hexahydroxydiphenoyl-β-d-glucopyranoside and 4,6-Di-O-galloyl-2,3-(R)-hexahydroxydiphenoyl-d-glucoside. The Proposed Chemical Structures for Cercidinin A and B Must Be Revised

  摘要：

  The total syntheses of the enantiomerically pure unusual ellagitannins 1,4,6-tri-O-galloyl-2,3-(R)-hexahydroxydiphenoyl-beta-D-glucopyranoside (1) and 4, 6-di-O-galloyl-2,3-(R)-hexahydroxydiphenoyl-D-glucoside (2) are reported. The NMR data of the synthetic ellagitannins 1 and 2 are not identical with those reported for cercidinin A and B. Thus, the proposed structures for cercidinin A and B must be revised.

  DOI：

  10.1021/jo9805302

文献信息

• Nonaka, Gen-ichiro; Ishimatsu, Makoto; Ageta, Masayuki, Chemical and pharmaceutical bulletin, 1989, vol. 37, # 1, p. 50 - 53
  作者：Nonaka, Gen-ichiro、Ishimatsu, Makoto、Ageta, Masayuki、Nishioka, Itsuo

  DOI：——

  日期：——
• Praecoxin B,C,D and E, novel ellagitannins from Stachyurus praecox.
  作者：Takuo Okuda、Tsutomu Hatano、Kazufumi Yazaki

  DOI：10.1248/cpb.31.333

  日期：——

  Praecoxin C (6), D (7) and E (8), ellagitannins having depside linkage, and praecoxin B (9), an isomer of tellimagrandin I (1), were isolated from Stachyurus praecox.

  从早春小水杉（Stachyurus praecox）中分离出了普雷香素C（6）、D（7）和E（8），这些是具有酯链的椰子单宁，以及普雷香素B（9），它是堇菜苷I（1）的异构体。
• Synthesis of Enantiomerically Pure Unusual Ellagitannins 1,4,6-Tri-<i>O</i>-galloyl-2,3-(<i>R</i>)-hexahydroxydiphenoyl-β-<scp>d</scp>-glucopyranoside and 4,6-Di-<i>O</i>-galloyl-2,3-(<i>R</i>)-hexahydroxydiphenoyl-<scp>d</scp>-glucoside. The Proposed Chemical Structures for Cercidinin A and B Must Be Revised
  作者：Karamali Khanbabaee、Kerstin Lötzerich

  DOI：10.1021/jo9805302

  日期：1998.11.1

  The total syntheses of the enantiomerically pure unusual ellagitannins 1,4,6-tri-O-galloyl-2,3-(R)-hexahydroxydiphenoyl-beta-D-glucopyranoside (1) and 4, 6-di-O-galloyl-2,3-(R)-hexahydroxydiphenoyl-D-glucoside (2) are reported. The NMR data of the synthetic ellagitannins 1 and 2 are not identical with those reported for cercidinin A and B. Thus, the proposed structures for cercidinin A and B must be revised.