(4aS,6aR,12aR,12bS)-8-Hydroxy-4,4,6a,12b-tetramethyl-1,3,4,4a,5,6,6a,12,12a,12b-decahydro-2H-benzo[a]xanthene-10-carboxylic acid methyl ester | 135823-99-3

• 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,12aR,12bS)-8-Hydroxy-4,4,6a,12b-tetramethyl-1,3,4,4a,5,6,6a,12,12a,12b-decahydro-2H-benzo[a]xanthene-10-carboxylic acid methyl ester
• 英文别名: methyl (4aS,6aR,12aR,12bS)-8-hydroxy-4,4,6a,12b-tetramethyl-1,2,3,4a,5,6,12,12a-octahydrobenzo[a]xanthene-10-carboxylate
• CAS: 135823-99-3
• 化学式: C₂₃H₃₂O₄
• 分子量: 372.505
• InChiKey: RYNPFSSOXCTDHA-OVNVTHAWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.9
• 重原子数：
  27
• 可旋转键数：
  2
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.7
• 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,12aR,12bS)-8-Hydroxy-4,4,6a,12b-tetramethyl-1,3,4,4a,5,6,6a,12,12a,12b-decahydro-2H-benzo[a]xanthene-10-carboxylic acid methyl ester 在 氢氧化钾 、 potassium carbonate 作用下， 以 丙酮 为溶剂， 反应 20.0h， 生成 (4aS,6aR,12aR,12bS)-8-Methoxy-4,4,6a,12b-tetramethyl-1,3,4,4a,5,6,6a,12,12a,12b-decahydro-2H-benzo[a]xanthene-10-carboxylic acid
  参考文献：
  名称：

  Smenochromenes, unusual macrocyclic sesquiterpene hydroquinone derivatives from a Seychelles sponge of the genus Smenospongia

  摘要：

  Smenochromenes A-D (2-5) are four unusual macrocyclic chromenes that can be derived by cyclization of farnesyl hydroquinone. The structure of smenochromene A (2) was determined by X-ray analysis and the structures of the remaining compounds were elucidated by interpretation of spectral data. The unusual geometry of smenochromene A gives rise to some unexpected spectral data. The sponge Smenospongia sp. also contains smenodiol (6), which is related to compounds previously found in this genus.

  DOI：

  10.1021/jo00022a011
• 作为产物：
  描述：

  smenodiol 在 盐酸 作用下， 以 乙醇 为溶剂， 反应 10.0h， 以8 mg的产率得到(4aS,6aR,12aR,12bS)-8-Hydroxy-4,4,6a,12b-tetramethyl-1,3,4,4a,5,6,6a,12,12a,12b-decahydro-2H-benzo[a]xanthene-10-carboxylic acid methyl ester
  参考文献：
  名称：

  线虫的细胞毒性倍半萜醌的结构和立体化学

  摘要：

  线虫（Dactylospongia elegans）粗提物的细胞毒性刺激了对活性成分的寻找。的结构和绝对立体化学被阐明为四个新的9，11,18，19，和13先前所描述的化合物，3，4，图6a，7，8，10，12 - 17，21。这些化合物是从斐济，巴布亚新几内亚和泰国三个不同的印度太平洋地区获得的秀丽线虫的集合中分离出来的。与其他海绵或海藻相比，该物种似乎更详细地描述了混合生物发生倍半萜烯-氢醌（-醌）代谢产物。三种化合物，4,9，和13，分别为有效的（IC 50小于1μg/ mL）。醌环对于这种体外活性似乎是必不可少的。

  DOI：

  10.1016/s0040-4020(01)80012-0

文献信息

• The structures and stereochemistry of cytotoxic sesquiterpene quinones from dactylospongia elegans
  作者：Jaime Rodríguez、Emilio Quiñoá、Ricardo Riguera、Barbara M. Peters、Leif M. Abrell、Phillip Crews

  DOI：10.1016/s0040-4020(01)80012-0

  日期：1992.1

  The cytotoxicity of a crude extract from Dactylospongia elegans stimulated a search for the active constituents. The structures and absolute stereochemistry are elucidated for four new 9, 11,18, 19, and thirteen previously described compounds, 3, 4, 6a, 7, 8, 10, 12 - 17, 21. These compounds were isolated from collections of D. elegans obtained from three different Indo-Pacific regions, Fiji, Papua

  线虫（Dactylospongia elegans）粗提物的细胞毒性刺激了对活性成分的寻找。的结构和绝对立体化学被阐明为四个新的9，11,18，19，和13先前所描述的化合物，3，4，图6a，7，8，10，12 - 17，21。这些化合物是从斐济，巴布亚新几内亚和泰国三个不同的印度太平洋地区获得的秀丽线虫的集合中分离出来的。与其他海绵或海藻相比，该物种似乎更详细地描述了混合生物发生倍半萜烯-氢醌（-醌）代谢产物。三种化合物，4,9，和13，分别为有效的（IC 50小于1μg/ mL）。醌环对于这种体外活性似乎是必不可少的。
• Smenochromenes, unusual macrocyclic sesquiterpene hydroquinone derivatives from a Seychelles sponge of the genus Smenospongia
  作者：Yenmandra Venkateswarlu、D. John Faulkner、Jorge L. Rios Steiner、Ethan Corcoran、Jon Clardy

  DOI：10.1021/jo00022a011

  日期：1991.10

  Smenochromenes A-D (2-5) are four unusual macrocyclic chromenes that can be derived by cyclization of farnesyl hydroquinone. The structure of smenochromene A (2) was determined by X-ray analysis and the structures of the remaining compounds were elucidated by interpretation of spectral data. The unusual geometry of smenochromene A gives rise to some unexpected spectral data. The sponge Smenospongia sp. also contains smenodiol (6), which is related to compounds previously found in this genus.