(4aR,8aR)-8a-allyl-4a-methylhexahydronaphthalene-1,6-(2H,7H)-dione | 1224845-39-9

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (4aR,8aR)-8a-allyl-4a-methylhexahydronaphthalene-1,6-(2H,7H)-dione
• 英文别名: (4aR,8aR)-4a-methyl-8a-prop-2-enyl-2,3,4,5,7,8-hexahydronaphthalene-1,6-dione
• CAS: 1224845-39-9
• 化学式: C₁₄H₂₀O₂
• 分子量: 220.312
• InChiKey: PYQBZQLNWNIJTJ-ZIAGYGMSSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  16
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.71
• 拓扑面积：
  34.1
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  2-乙基-2-甲基-1,3-二氧杂烷 、 (4aR,8aR)-8a-allyl-4a-methylhexahydronaphthalene-1,6-(2H,7H)-dione 在 对甲苯磺酸 作用下， 反应 1.0h， 生成 (4aR,8aR)-4a-allyl-8a-methylhexahydro-1H-spiro[naphthalene-2,2'-[1,3]dioxolan]-5(3H)-one
  参考文献：
  名称：

  Total Synthesis of (−)-Anominine

  摘要：

  The first total synthesis of anominine has been achieved, and the absolute configuration of the product has been determined. The key features include the development of a new, highly efficient organocatalyzed method for the asymmetric synthesis of Wieland-Miescher ketone building blocks, an unusual selenoxide [2,3]-sigmatropic rearrangement, and a ZrCl(4)-catalyzed indole coupling as well as several chemoselective transformations controlled by the structurally congested nature of the bicyclic core.

  DOI：

  10.1021/ja101994q
• 作为产物：
  描述：

  甲基锂 、 (R)-3,4,8,8a-tetrahydro-8a-allyl-1,6-(2H,7H)-naphthalenedione 在 copper(l) iodide 、 水 、 氯化铵 作用下， 以 乙醚 为溶剂， 反应 3.5h， 以79%的产率得到(4aR,8aR)-8a-allyl-4a-methylhexahydronaphthalene-1,6-(2H,7H)-dione
  参考文献：
  名称：

  Total Synthesis of (−)-Anominine

  摘要：

  The first total synthesis of anominine has been achieved, and the absolute configuration of the product has been determined. The key features include the development of a new, highly efficient organocatalyzed method for the asymmetric synthesis of Wieland-Miescher ketone building blocks, an unusual selenoxide [2,3]-sigmatropic rearrangement, and a ZrCl(4)-catalyzed indole coupling as well as several chemoselective transformations controlled by the structurally congested nature of the bicyclic core.

  DOI：

  10.1021/ja101994q

文献信息

• Total Synthesis of (−)-Anominine
  作者：Ben Bradshaw、Gorka Etxebarria-Jardí、Josep Bonjoch

  DOI：10.1021/ja101994q

  日期：2010.5.5

  The first total synthesis of anominine has been achieved, and the absolute configuration of the product has been determined. The key features include the development of a new, highly efficient organocatalyzed method for the asymmetric synthesis of Wieland-Miescher ketone building blocks, an unusual selenoxide [2,3]-sigmatropic rearrangement, and a ZrCl(4)-catalyzed indole coupling as well as several chemoselective transformations controlled by the structurally congested nature of the bicyclic core.