(4aS,6aR,12bS)-4,4,6a,9,12b-pentamethyl-2,3,4a,5,6,8,9,10-octahydro-1H-benzo[a]xanthen-11-one | 892725-59-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 萘并吡喃类
• 英文名称: (4aS,6aR,12bS)-4,4,6a,9,12b-pentamethyl-2,3,4a,5,6,8,9,10-octahydro-1H-benzo[a]xanthen-11-one
• CAS: 892725-59-6
• 化学式: C₂₂H₃₂O₂
• 分子量: 328.495
• InChiKey: LFSCCGHIJWZAEF-GXGPIRRHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.1
• 重原子数：
  24
• 可旋转键数：
  0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.77
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (4aS,6aR,12bS)-4,4,6a,9,12b-pentamethyl-2,3,4a,5,6,8,9,10-octahydro-1H-benzo[a]xanthen-11-one 在 2,3-二氯-5,6-二氰基-1,4-苯醌 、 lithium diisopropyl amide 作用下， 以 四氢呋喃 、 苯 为溶剂， 反应 50.0h， 生成 (4aS,6aR,12bS)-11-Hydroxy-4,4,6a,9,12b-pentamethyl-1,3,4,4a,5,6,6a,12b-octahydro-2H-benzo[a]xanthene-10-carboxylic acid methyl ester
  参考文献：
  名称：

  An Unusual Cationic [2 + 2] Cycloaddition in a Divergent Total Synthesis of Hongoquercin A and Rhododaurichromanic Acid A

  摘要：

  An unusual polyene cyclization pathway that led to a divergent total synthesis of hongoquercin A and rhododaurichromanic acid A is described here. This work uncovered a unique cationic cyclobutane formation that could be relevant to the biosynthetic pathway for the formation of cyclobutane containing terpenoids in addition to rhododaurichromanic acids.

  DOI：

  10.1021/ja054872i
• 作为产物：
  描述：

  5-甲基环己烷-1,3-二酮 、 (4aS,8aS)-3,4,4a,5,6,7,8,8a-octahydro-2,5,5,8a-tetramethylnaphthalene-1-carboxaldehyde 在 哌啶乙酸盐 、 sodium sulfate 作用下， 以 乙酸乙酯 为溶剂， 反应 16.0h， 以66%的产率得到(4aS,6aR,12bS)-4,4,6a,9,12b-pentamethyl-2,3,4a,5,6,8,9,10-octahydro-1H-benzo[a]xanthen-11-one
  参考文献：
  名称：

  An Unusual Cationic [2 + 2] Cycloaddition in a Divergent Total Synthesis of Hongoquercin A and Rhododaurichromanic Acid A

  摘要：

  An unusual polyene cyclization pathway that led to a divergent total synthesis of hongoquercin A and rhododaurichromanic acid A is described here. This work uncovered a unique cationic cyclobutane formation that could be relevant to the biosynthetic pathway for the formation of cyclobutane containing terpenoids in addition to rhododaurichromanic acids.

  DOI：

  10.1021/ja054872i

文献信息

• An Unusual Cationic [2 + 2] Cycloaddition in a Divergent Total Synthesis of Hongoquercin A and Rhododaurichromanic Acid A
  作者：Aleksey V. Kurdyumov、Richard P. Hsung

  DOI：10.1021/ja054872i

  日期：2006.5.1

  An unusual polyene cyclization pathway that led to a divergent total synthesis of hongoquercin A and rhododaurichromanic acid A is described here. This work uncovered a unique cationic cyclobutane formation that could be relevant to the biosynthetic pathway for the formation of cyclobutane containing terpenoids in addition to rhododaurichromanic acids.