<1S-(1α,3aβ,7aα)>-Octahydro-1-<(tert-butyldimethylsilyl)oxy>-7a-methyl-4H-inden-4-one | 140659-42-3

• 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,3aβ,7aα)>-Octahydro-1-<(tert-butyldimethylsilyl)oxy>-7a-methyl-4H-inden-4-one
• 英文别名: (1S,3aR,7aS)-1-[tert-butyl(dimethyl)silyl]oxy-7a-methyl-2,3,3a,5,6,7-hexahydro-1H-inden-4-one
• CAS: 140659-42-3
• 化学式: C₁₆H₃₀O₂Si
• 分子量: 282.498
• InChiKey: JZTJWVUUDLVCNT-NOLJZWGESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.55
• 重原子数：
  19
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.94
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  <1S-(1α,3aβ,7aα)>-Octahydro-1-<(tert-butyldimethylsilyl)oxy>-7a-methyl-4H-inden-4-one 在 sodium tetrahydroborate 、 氢氟酸 作用下， 以 乙醇 、 乙腈 为溶剂， 反应 1.0h， 生成 <1S-(1α,3aβ,4α,7aα)>-Octahydro-1,4-dihydroxy-7a-methyl-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
• 作为产物：
  描述：

  <1S-(1α,7aα)>-2,3,5,6,7,7a-Hexahydro-1-<(tert-butyldimethylsilyl)oxy>-7a-methyl-4-<(trimethylsilyl)oxy>-1H-indene 在 三乙基硼 、 三正丁基氢锡 作用下， 以 乙醚 、 甲苯 为溶剂， 反应 0.75h， 生成 <1S-(1α,3aβ,7aα)>-Octahydro-1-<(tert-butyldimethylsilyl)oxy>-7a-methyl-4H-inden-4-one
  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

文献信息

• Synthesis of hydrindan derivatives related to vitamin D
  作者：Benito Fernandez、Jose A. Martinez Perez、Juan R. Granja、Luis Castedo、Antonio Mourino

  DOI：10.1021/jo00037a039

  日期：1992.5

  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.