<1S-(1α,4β,7aα)>-2,4,5,6,7,7a-Hexahydro-1-<(tert-butyldimethylsilyl)oxy>-7a-methyl-1H-inden-4-ol | 140659-37-6

• 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,4β,7aα)>-2,4,5,6,7,7a-Hexahydro-1-<(tert-butyldimethylsilyl)oxy>-7a-methyl-1H-inden-4-ol
• 英文别名: (1S,4R,7aS)-1-[tert-butyl(dimethyl)silyl]oxy-7a-methyl-1,2,4,5,6,7-hexahydroinden-4-ol
• CAS: 140659-37-6
• 化学式: C₁₆H₃₀O₂Si
• 分子量: 282.498
• InChiKey: RROCFLXIFFVBLB-YCPHGPKFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.26
• 重原子数：
  19
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.88
• 拓扑面积：
  29.5
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  <1S-(1α,4β,7aα)>-2,4,5,6,7,7a-Hexahydro-1-<(tert-butyldimethylsilyl)oxy>-7a-methyl-1H-inden-4-ol 在 Crabtree catalyst 氢气 作用下， 以 二氯甲烷 为溶剂， 反应 30.0h， 以92%的产率得到<1S-(1α,3aα,4β,7aα)>-Octahydro-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)>-1,2,5,6,7,7a-Hexahydro-1-<(tert-butyldimethylsilyl)oxy>-7a-methyl-4H-inden-4-one 在 sodium tetrahydroborate 、 cerium(III) chloride 作用下， 以 甲醇 为溶剂， 反应 0.25h， 以92%的产率得到<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