(5SR,6RS)-1-(6-hydroxy-1,3,9,11-tetramethoxy-2,10-dihydroxy-6-methyl-6,7-dihydro-5H-dibenzo[a,c]cyclohepten-5-yl)ethanone

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 单宁
• 英文名称: (5SR,6RS)-1-(6-hydroxy-1,3,9,11-tetramethoxy-2,10-dihydroxy-6-methyl-6,7-dihydro-5H-dibenzo[a,c]cyclohepten-5-yl)ethanone
• 英文别名: 1-[(8S,9R)-4,9,14-trihydroxy-3,5,13,15-tetramethoxy-9-methyl-8-tricyclo[9.4.0.02,7]pentadeca-1(15),2,4,6,11,13-hexaenyl]ethanone
• 化学式: C₂₂H₂₆O₈
• 分子量: 418.444
• InChiKey: WXAOJPLKJNVQAR-HTAPYJJXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  30
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.41
• 拓扑面积：
  115
• 氢给体数：
  3
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  甲基苯基亚砜 、 (5SR,6RS)-1-(6-hydroxy-1,3,9,11-tetramethoxy-2,10-dihydroxy-6-methyl-6,7-dihydro-5H-dibenzo[a,c]cyclohepten-5-yl)ethanone 以 正己烷 、 苯 为溶剂， 反应 12.0h， 生成
  参考文献：
  名称：

  Synthesis of the Cores of Hypocrellin and Shiraiachrome: Diastereoselective 1,8-Diketone Aldol Cyclization

  摘要：

  Intramolecular 1,8-diketone aldol reactions Were Studied as a tool for the construction of the seven-membered rings of hypocrellin and shiraiachrome. Conditions were identified to obtain the relative stereochemistries present in the two natural products with excellent diastereoselectivity. In addition, a nine-membered ring congener, which has yet to be observed in nature, formed with high selectivity when a hindered amine was used in conjunction with silazide bases.

  DOI：

  10.1021/jo9018914
• 作为产物：
  描述：

  (5SR,6RS)-1-(6-hydroxy-1,3,9,11-tetramethoxy-2,10-dibenzyloxy-6-methyl-6,7-dihydro-5H-dibenzo[a,c]cyclohepten-5-yl)ethanone 在 palladium 10% on activated carbon 、 氢气 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 反应 0.33h， 以100%的产率得到(5SR,6RS)-1-(6-hydroxy-1,3,9,11-tetramethoxy-2,10-dihydroxy-6-methyl-6,7-dihydro-5H-dibenzo[a,c]cyclohepten-5-yl)ethanone
  参考文献：
  名称：

  Synthesis of the Cores of Hypocrellin and Shiraiachrome: Diastereoselective 1,8-Diketone Aldol Cyclization

  摘要：

  Intramolecular 1,8-diketone aldol reactions Were Studied as a tool for the construction of the seven-membered rings of hypocrellin and shiraiachrome. Conditions were identified to obtain the relative stereochemistries present in the two natural products with excellent diastereoselectivity. In addition, a nine-membered ring congener, which has yet to be observed in nature, formed with high selectivity when a hindered amine was used in conjunction with silazide bases.

  DOI：

  10.1021/jo9018914

文献信息

• Synthesis of the Cores of Hypocrellin and Shiraiachrome: Diastereoselective 1,8-Diketone Aldol Cyclization
  作者：Erin M. O’Brien、Jingxian Li、Patrick J. Carroll、Marisa C. Kozlowski

  DOI：10.1021/jo9018914

  日期：2010.1.1

  Intramolecular 1,8-diketone aldol reactions Were Studied as a tool for the construction of the seven-membered rings of hypocrellin and shiraiachrome. Conditions were identified to obtain the relative stereochemistries present in the two natural products with excellent diastereoselectivity. In addition, a nine-membered ring congener, which has yet to be observed in nature, formed with high selectivity when a hindered amine was used in conjunction with silazide bases.