<1S-(1α,7aα)>-2,3,5,6,7,7a-Hexahydro-1-<(tert-butyldimethylsilyl)oxy>-7a-methyl-4-<(trimethylsilyl)oxy>-1H-indene | 140676-27-3

• 分子结构分类: 有机化合物 - 有机金属化合物 - 有机类金属化合物
• 英文名称: <1S-(1α,7aα)>-2,3,5,6,7,7a-Hexahydro-1-<(tert-butyldimethylsilyl)oxy>-7a-methyl-4-<(trimethylsilyl)oxy>-1H-indene
• CAS: 140676-27-3
• 化学式: C₁₉H₃₈O₂Si₂
• 分子量: 354.681
• InChiKey: TVKFBLDZQOFVBJ-HKUYNNGSSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.47
• 重原子数：
  23.0
• 可旋转键数：
  4.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.89
• 拓扑面积：
  18.46
• 氢给体数：
  0.0
• 氢受体数：
  2.0

反应信息

• 作为反应物：
  描述：

  <1S-(1α,7aα)>-2,3,5,6,7,7a-Hexahydro-1-<(tert-butyldimethylsilyl)oxy>-7a-methyl-4-<(trimethylsilyl)oxy>-1H-indene 在 sodium tetrahydroborate 、 cerium(III) chloride 、 间氯过氧苯甲酸 作用下， 以 甲醇 、 乙醚 、 二氯甲烷 为溶剂， 反应 8.5h， 生成 <1S-(1α,4β,7aα)>-2,4,5,6,7,7a-Hexahydro-1-<(tert-butyldimethylsilyl)oxy>-7a-methyl-1H-inden-4-ol
  参考文献：
  名称：

  Synthesis of hydrindan derivatives related to vitamin D

  摘要：

  Two independent routes to the CD fragment of vitamin D metabolites and analogues are described. The trans-hydrindanol 4 was synthesized from enedione 5. The key step in this synthesis was the hydroxyl-directed hydrogenation of hydrindenols of type 15 in the presence of Wilkinson's catalyst. The trans-hydrindanone 6 was efficiently prepared by degradation of the Lythgoe-Inhoffen diol (3). Both 4 and 6 are suitable precursors for the preparation of new potentially useful analogues of 1-alpha,25-dihydroxyvitamin D3 that are functionalized at C20, C21, or ring D.

  DOI：

  10.1021/jo00037a039
• 作为产物：
  描述：

  <1S-(1α,7aα)>-2,3,5,6,7,7a-Hexahydro-1,5-bis(acetyloxy)-7a-methyl-1H-indene 在 咪唑 、 sodium hydroxide 、 重铬酸吡啶 、 氨 、 双氧水 、 lithium 、 六甲基二硅氮烷 、 lithium iodide 、 diborane(6) 作用下， 以 乙醚 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 49.5h， 生成 <1S-(1α,7aα)>-2,3,5,6,7,7a-Hexahydro-1-<(tert-butyldimethylsilyl)oxy>-7a-methyl-4-<(trimethylsilyl)oxy>-1H-indene
  参考文献：
  名称：

  Synthesis of hydrindan derivatives related to vitamin D

  摘要：

  Two independent routes to the CD fragment of vitamin D metabolites and analogues are described. The trans-hydrindanol 4 was synthesized from enedione 5. The key step in this synthesis was the hydroxyl-directed hydrogenation of hydrindenols of type 15 in the presence of Wilkinson's catalyst. The trans-hydrindanone 6 was efficiently prepared by degradation of the Lythgoe-Inhoffen diol (3). Both 4 and 6 are suitable precursors for the preparation of new potentially useful analogues of 1-alpha,25-dihydroxyvitamin D3 that are functionalized at C20, C21, or ring D.

  DOI：

  10.1021/jo00037a039