[(1S,4R,7aR)-7a-methyl-1-(2-methyl-1,3-dioxolan-2-yl)-1,2,4,5,6,7-hexahydroinden-4-yl]methyl benzoate | 160146-85-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: [(1S,4R,7aR)-7a-methyl-1-(2-methyl-1,3-dioxolan-2-yl)-1,2,4,5,6,7-hexahydroinden-4-yl]methyl benzoate
• CAS: 160146-85-0
• 化学式: C₂₂H₂₈O₄
• 分子量: 356.462
• InChiKey: QBSASDWEDUOZEA-CUWPLCDZSA-N

物化性质

• 沸点：
  459.2±45.0 °C(predicted)
• 密度：
  1.16±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.2
• 重原子数：
  26
• 可旋转键数：
  5
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.59
• 拓扑面积：
  44.8
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  [(1S,4R,7aR)-7a-methyl-1-(2-methyl-1,3-dioxolan-2-yl)-1,2,4,5,6,7-hexahydroinden-4-yl]methyl benzoate 在 palladium on activated charcoal 氢气 、 碳酸氢钠 作用下， 反应 14.0h， 生成 [(1S,3aS,4R,7aS)-7a-methyl-1-(2-methyl-1,3-dioxolan-2-yl)-1,2,3,3a,4,5,6,7-octahydroinden-4-yl]methyl benzoate
  参考文献：
  名称：

  A New Candidate for a Properly Substituted CD Ring Component of Vitamin D3 via Intramolecular Asymmetric Olefination of a 1,3-Cyclopentanedione Derivative

  摘要：

  A highly diastereoselective synthesis of hydrindenone derivative 5 (98% de) was achieved via diastereotopic differentiation of 1,3-cyclopentanedione derivative 4 by intramolecular Horner-Emmons olefination. In addition, the compound 5 was converted to ketone 2, a new building block far 1 alpha,25-dihydroxyvitamin D-3 (1).

  DOI：

  10.1021/jo00099a002
• 作为产物：
  描述：

  [(1R,2S,5R)-5-methyl-2-(2-phenylpropan-2-yl)cyclohexyl] (1R,7aS)-1-methoxycarbonyloxy-7a-methyl-1-prop-1-en-2-yl-3,5,6,7-tetrahydro-2H-indene-4-carboxylate 在 bis(acetylacetonato)palladium(II) 、 三丁基膦 、 三氟甲磺酸三甲基硅酯 吡啶 、 sodium periodate 、 四氧化锇 、 lithium aluminium tetrahydride 、 甲酸 、 三乙胺 、 乙酰氯 、 lithium diisopropyl amide 作用下， 以 1,4-二氧六环 、 乙醚 、 二氯甲烷 、 水 、 丙酮 、 苯 为溶剂， 反应 13.17h， 生成 [(1S,4R,7aR)-7a-methyl-1-(2-methyl-1,3-dioxolan-2-yl)-1,2,4,5,6,7-hexahydroinden-4-yl]methyl benzoate
  参考文献：
  名称：

  A New Candidate for a Properly Substituted CD Ring Component of Vitamin D3 via Intramolecular Asymmetric Olefination of a 1,3-Cyclopentanedione Derivative

  摘要：

  A highly diastereoselective synthesis of hydrindenone derivative 5 (98% de) was achieved via diastereotopic differentiation of 1,3-cyclopentanedione derivative 4 by intramolecular Horner-Emmons olefination. In addition, the compound 5 was converted to ketone 2, a new building block far 1 alpha,25-dihydroxyvitamin D-3 (1).

  DOI：

  10.1021/jo00099a002

文献信息

• A New Candidate for a Properly Substituted CD Ring Component of Vitamin D3 via Intramolecular Asymmetric Olefination of a 1,3-Cyclopentanedione Derivative
  作者：Tadakatsu Mandai、Yuichi Kaihara、Jiro Tsuji

  DOI：10.1021/jo00099a002

  日期：1994.10

  A highly diastereoselective synthesis of hydrindenone derivative 5 (98% de) was achieved via diastereotopic differentiation of 1,3-cyclopentanedione derivative 4 by intramolecular Horner-Emmons olefination. In addition, the compound 5 was converted to ketone 2, a new building block far 1 alpha,25-dihydroxyvitamin D-3 (1).