(1R,4S,4aR,8aR)-8a-allyl-4,4a-dimethyl-8-methylene-1,4,4a,5,6,7,8,8a-octahydronaphthalen-1-ol | 1224845-46-8

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (1R,4S,4aR,8aR)-8a-allyl-4,4a-dimethyl-8-methylene-1,4,4a,5,6,7,8,8a-octahydronaphthalen-1-ol
• 英文别名: (1R,4S,4aR,8aR)-4,4a-dimethyl-8-methylidene-8a-prop-2-enyl-4,5,6,7-tetrahydro-1H-naphthalen-1-ol
• CAS: 1224845-46-8
• 化学式: C₁₆H₂₄O
• 分子量: 232.366
• InChiKey: XBIUSDYTGRCAER-XZDPQHSOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4
• 重原子数：
  17
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.62
• 拓扑面积：
  20.2
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  (1R,4S,4aR,8aR)-8a-allyl-4,4a-dimethyl-8-methylene-1,4,4a,5,6,7,8,8a-octahydronaphthalen-1-ol 、 三乙基硅基三氟甲磺酸酯 在 2,6-二甲基吡啶 作用下， 以 二氯甲烷 为溶剂， 反应 0.5h， 以83%的产率得到
  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：

  在 乙醇 、 sodium methylate 作用下， 反应 0.5h， 以740 mg的产率得到(1R,4S,4aR,8aR)-8a-allyl-4,4a-dimethyl-8-methylene-1,4,4a,5,6,7,8,8a-octahydronaphthalen-1-ol
  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.