(4'aR,5'S,7'R,10'S,11'S,12'aR)-decahydro-4'a,13',13'-trimethylspiro<1,3-dithiolane-2,1'(2'H)-<7,10>methanobenzocyclodecene>-5',10',11'(5'H)-triol | 124126-53-0

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 异戊烯醇脂质
• 英文名称: (4'aR,5'S,7'R,10'S,11'S,12'aR)-decahydro-4'a,13',13'-trimethylspiro<1,3-dithiolane-2,1'(2'H)-<7,10>methanobenzocyclodecene>-5',10',11'(5'H)-triol
• CAS: 124126-53-0；132881-70-0
• 化学式: C₂₀H₃₄O₃S₂
• 分子量: 386.62
• InChiKey: NOHRSHZLKAASMA-FLDBGCDGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.65
• 重原子数：
  25.0
• 可旋转键数：
  0.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  60.69
• 氢给体数：
  3.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  (4'aR,5'S,7'R,10'S,11'S,12'aR)-decahydro-4'a,13',13'-trimethylspiro<1,3-dithiolane-2,1'(2'H)-<7,10>methanobenzocyclodecene>-5',10',11'(5'H)-triol 在 吡啶 、 N-[(2,4-二氯苯氧基)-甲氧基硫代膦酰]丙-2-胺 、 4-甲基苯磺酰溴 、 potassium carbonate 作用下， 以 甲醇 、 水 为溶剂， 生成 (4'aR,5'S,7'R,10'R,11'E,12'aR)-3',4',4'a,6',7',8',9',12'a-octahydro-4'a,13',13'-trimethylspiro<1,3-dithiolane-2,1'(2'H)-<7,10>methanobenzocyclodecene>-5',10'(5'H)-diol 5'-acetate
  参考文献：
  名称：

  Functionalization reactions of a medium-ring bridgehead enone that skirt transannular bond formation

  摘要：

  As a consequence of the close proximity of the olefinic and carbonyl centers in ketone 4, the molecule participates readily in transannular reactions. Sequences have been developed for enhancing the level of functionality in both of these sectors within the central medium-sized ring without incurring ring closure. Osmate ester 10 is especially serviceable, permitting direct access to triol 11 and to the olefinic hydroxy acetate 17. In a companion study, acetals 19a and 19b were prepared from 11 and dehydrated with the Burgess reagent. The trans cycloalkene generated in each instance was shown to possess the topography found in 21, a conclusion that was further supported by deuterium labeling experiments. Access to this diastereomer made possible the acquisition of diacetates 23a and 23b, where seven of the nine carbon atoms of the central ring are stereogenic and have well-defined absolute stereochemistry.

  DOI：

  10.1021/jo00007a038
• 作为产物：
  描述：

  在 吡啶 、 四氧化锇 、 lithium aluminium tetrahydride 作用下， 生成 (4'aR,5'S,7'R,10'S,11'S,12'aR)-decahydro-4'a,13',13'-trimethylspiro<1,3-dithiolane-2,1'(2'H)-<7,10>methanobenzocyclodecene>-5',10',11'(5'H)-triol
  参考文献：
  名称：

  Functionalization reactions of a medium-ring bridgehead enone that skirt transannular bond formation

  摘要：

  As a consequence of the close proximity of the olefinic and carbonyl centers in ketone 4, the molecule participates readily in transannular reactions. Sequences have been developed for enhancing the level of functionality in both of these sectors within the central medium-sized ring without incurring ring closure. Osmate ester 10 is especially serviceable, permitting direct access to triol 11 and to the olefinic hydroxy acetate 17. In a companion study, acetals 19a and 19b were prepared from 11 and dehydrated with the Burgess reagent. The trans cycloalkene generated in each instance was shown to possess the topography found in 21, a conclusion that was further supported by deuterium labeling experiments. Access to this diastereomer made possible the acquisition of diacetates 23a and 23b, where seven of the nine carbon atoms of the central ring are stereogenic and have well-defined absolute stereochemistry.

  DOI：

  10.1021/jo00007a038