(1R,7aR)-1-[(2R)-4-hydroxybutan-2-yl]-7a-methyl-2,5,6,7-tetrahydro-1H-inden-4-one | 146434-07-3

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (1R,7aR)-1-[(2R)-4-hydroxybutan-2-yl]-7a-methyl-2,5,6,7-tetrahydro-1H-inden-4-one
• CAS: 146434-07-3
• 化学式: C₁₄H₂₂O₂
• 分子量: 222.327
• InChiKey: ZGYIHEMMTJJXFU-JTNHKYCSSA-N

物化性质

• 沸点：
  356.7±11.0 °C(predicted)
• 密度：
  1.05±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  16
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.79
• 拓扑面积：
  37.3
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (1R,7aR)-1-[(2R)-4-hydroxybutan-2-yl]-7a-methyl-2,5,6,7-tetrahydro-1H-inden-4-one 在 palladium on activated charcoal 、 RhCl(PPh₃)3 咪唑 、 sodium tetrahydroborate 、 lithium aluminium tetrahydride 、 重铬酸吡啶 、 cerium(III) chloride 、 四丁基氟化铵 、 氢气 、 potassium hydride 、 sodium hydride 、 magnesium 作用下， 以 四氢呋喃 、 乙醚 、 乙醇 、 二氯甲烷 、 N,N-二甲基甲酰胺 、 paraffin 为溶剂， -78.0~25.0 ℃ 、101.33 kPa 条件下， 反应 140.67h， 生成 (1R,3aR,7aR)-1-{(1R)-1,5-dimethyl-5-[(trimethylsilyl)oxy]hexyl}-7a-methyloctahydro-4H-inden-4-one
  参考文献：
  名称：

  Stereoselective synthesis of cyclopentanones by reductive cleavage of 6-oxonorbornane-2-carboxylates and its application to the synthesis of 1.alpha.,25-dihydroxyvitamin D3 CD ring

  摘要：

  A novel chiral synthesis of the CD-ring 2 of 1alpha,25-dihydroxyvitamin D3 (1a) is described. The optically active D-ring keto ester 3c was prepared by reductive cleavage of 6-oxonorbornane-2-carboxylate 4c with lithium naphthalenide. 1,2-Transposition of enone 15, which was obtained by Robinson annulation of 14, was accomplished via thermolysis of the allylic carbonate 29 at 100-degrees-C to give enone 16. Reduction of ketone 16 with NaBH4-CeCl3 followed by hydrogenation with RhCl-(PPh3)3 catalyst gave trans-indanol 32, which was transformed to intermediate 2.

  DOI：

  10.1021/jo00058a032
• 作为产物：
  描述：

  <1R-(1α,5α,7aα)>-1-<(1R)-3-<(tert-butyldiphenylsilyl)oxy>-1-methylpropyl>-2,3,5,6,7,7a-hexahydro-4-methoxy-7a-methyl-1H-inden-5-ol 在 吡啶 、 4-二甲氨基吡啶 作用下， 以 二氯甲烷 、 二甲基亚砜 为溶剂， 反应 2.67h， 生成 (1R,7aR)-1-[(2R)-4-hydroxybutan-2-yl]-7a-methyl-2,5,6,7-tetrahydro-1H-inden-4-one
  参考文献：
  名称：

  Stereoselective synthesis of cyclopentanones by reductive cleavage of 6-oxonorbornane-2-carboxylates and its application to the synthesis of 1.alpha.,25-dihydroxyvitamin D3 CD ring

  摘要：

  A novel chiral synthesis of the CD-ring 2 of 1alpha,25-dihydroxyvitamin D3 (1a) is described. The optically active D-ring keto ester 3c was prepared by reductive cleavage of 6-oxonorbornane-2-carboxylate 4c with lithium naphthalenide. 1,2-Transposition of enone 15, which was obtained by Robinson annulation of 14, was accomplished via thermolysis of the allylic carbonate 29 at 100-degrees-C to give enone 16. Reduction of ketone 16 with NaBH4-CeCl3 followed by hydrogenation with RhCl-(PPh3)3 catalyst gave trans-indanol 32, which was transformed to intermediate 2.

  DOI：

  10.1021/jo00058a032