(4aR,8aR)-4a-allyl-8a-methyl-5-methylene-4a,5,6,7,8,8a-hexahydronaphthalen-2(1H)-one | 1224845-42-4

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (4aR,8aR)-4a-allyl-8a-methyl-5-methylene-4a,5,6,7,8,8a-hexahydronaphthalen-2(1H)-one
• 英文别名: (4aR,8aR)-8a-methyl-5-methylidene-4a-prop-2-enyl-1,6,7,8-tetrahydronaphthalen-2-one
• CAS: 1224845-42-4
• 化学式: C₁₅H₂₀O
• 分子量: 216.323
• InChiKey: HUTZRXSDYKUCPG-HUUCEWRRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  16
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.53
• 拓扑面积：
  17.1
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  (4aR,8aR)-4a-allyl-8a-methyl-5-methylene-4a,5,6,7,8,8a-hexahydronaphthalen-2(1H)-one 、 n,n-二甲基亚甲基碘化胺 在 lithium hexamethyldisilazane 作用下， 以 四氢呋喃 为溶剂， 反应 2.08h， 生成
  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：

  (4aS,8aR)-8a-methyl-5-methylidene-4a-prop-2-enyl-1,3,4,6,7,8-hexahydronaphthalen-2-one 在 对甲苯磺酸 、 2-碘酰基苯甲酸 作用下， 以 二甲基亚砜 为溶剂， 反应 16.0h， 以65%的产率得到(4aR,8aR)-4a-allyl-8a-methyl-5-methylene-4a,5,6,7,8,8a-hexahydronaphthalen-2(1H)-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

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.