(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 | 892725-49-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并吡喃
• 英文名称: (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
• 英文别名: methyl (4aS,6aR,12bS)-11-hydroxy-4,4,6a,9,12b-pentamethyl-1,2,3,4a,5,6-hexahydrobenzo[a]xanthene-10-carboxylate
• CAS: 892725-49-4
• 化学式: C₂₄H₃₂O₄
• 分子量: 384.516
• InChiKey: DLOQXWKEGNPDDL-YRUKQIKQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.4
• 重原子数：
  28
• 可旋转键数：
  2
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.62
• 拓扑面积：
  55.8
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (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 在 三乙基硅烷 、 三氟乙酸 作用下， 以 二氯甲烷 为溶剂， 反应 96.0h， 以99%的产率得到(4aS,6aR,12aR,12bS)-methyl 11-hydroxy-4,4,6a,9,12b-pentamethyl-2,3,4,4a,5,6,6a,12,12a,12b-decahydro-1H-benzo[a]xanthene-10-carboxylate
  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：

  (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

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.