(1R,2R,6R,10R,11R)-10,13-dihydroxy-2,6-dimethyl-3,9-dioxo-8,12-dioxatetracyclo[9.2.1.01,5.06,10]tetradec-4-ene-13-carboxylic acid | 427887-12-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 内酯类
• 英文名称: (1R,2R,6R,10R,11R)-10,13-dihydroxy-2,6-dimethyl-3,9-dioxo-8,12-dioxatetracyclo[9.2.1.01,5.06,10]tetradec-4-ene-13-carboxylic acid
• CAS: 427887-12-5
• 化学式: C₁₅H₁₆O₈
• 分子量: 324.287
• InChiKey: WTIVGGCMSDVDHS-TWABYVICSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1.4
• 重原子数：
  23
• 可旋转键数：
  1
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  130
• 氢给体数：
  3
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  甲醇 、 (1R,2R,6R,10R,11R)-10,13-dihydroxy-2,6-dimethyl-3,9-dioxo-8,12-dioxatetracyclo[9.2.1.01,5.06,10]tetradec-4-ene-13-carboxylic acid 以 丙酮 为溶剂， 反应 0.25h， 以46%的产率得到(-)-jiadifenin
  参考文献：
  名称：

  Total Synthesis of (−)-Jiadifenin

  摘要：

  As easy as ABCD: (-)-Jiadifenin was synthesized in eighteen reaction steps from 1-[(E)-(4'-bromo-2'-butenyl)oxy]-4-methoxybenzene. Key features of this synthesis include: 1) Ireland-Claisen rearrangement to produce the two contiguous quaternary centers at C5 and C6 simultaneously, 2) intramolecular Pauson-Khand reaction (IMPKR) to concurrently construct the A and B rings, and 3) [2+2] photo-cycloaddition to generate the all-carbon quaternary center at C9.

  DOI：

  10.1002/anie.201203176
• 作为产物：
  描述：

  (1R,10S)-2-oxo-3,4-dehydroxyneomajucin 在 Jones reagent 作用下， 以 丙酮 为溶剂， 反应 0.33h， 生成 (1R,2R,6R,10R,11R)-10,13-dihydroxy-2,6-dimethyl-3,9-dioxo-8,12-dioxatetracyclo[9.2.1.01,5.06,10]tetradec-4-ene-13-carboxylic acid
  参考文献：
  名称：

  Total Synthesis of (−)-Jiadifenin

  摘要：

  As easy as ABCD: (-)-Jiadifenin was synthesized in eighteen reaction steps from 1-[(E)-(4'-bromo-2'-butenyl)oxy]-4-methoxybenzene. Key features of this synthesis include: 1) Ireland-Claisen rearrangement to produce the two contiguous quaternary centers at C5 and C6 simultaneously, 2) intramolecular Pauson-Khand reaction (IMPKR) to concurrently construct the A and B rings, and 3) [2+2] photo-cycloaddition to generate the all-carbon quaternary center at C9.

  DOI：

  10.1002/anie.201203176