(4aS,8aR)-8a-methyl-5-methylidene-4a-prop-2-enyl-1,3,4,6,7,8-hexahydronaphthalen-2-one

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (4aS,8aR)-8a-methyl-5-methylidene-4a-prop-2-enyl-1,3,4,6,7,8-hexahydronaphthalen-2-one
• 化学式: C₁₅H₂₂O
• 分子量: 218.339
• InChiKey: GKXUIPKWRFCBJO-HUUCEWRRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  16
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.67
• 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：

  (4aS,8aR)-8a-methyl-5-methylidene-4a-prop-2-enyl-1,3,4,6,7,8-hexahydronaphthalen-2-one 在 Hoveyda-Grubbs catalyst second generation 、 iron(III)-acetylacetonate 、 苯硅烷 作用下， 以 乙醇 为溶剂， 反应 72.0h， 生成 (1RS,3aSR,4SR,7aSR)-4,7a-dimethyl-3a-(3-methylbut-2-en-1-yl)octahydro-1H-1,4-methanoinden-1-ol
  参考文献：
  名称：

  氢原子转移引发的烯键式酮的自由基环化

  摘要：

  描述了在EtOH中使用Fe（acac）3和PhSiH 3通过氢原子转移实现烯烃与酮之间前所未有的C-C偶联反应。这种温和的方案具有很高的位点选择性，并允许构建含有叔醇和季中心的空间拥挤结构。整个过程为开环反应引入了一种新颖的策略性键断开。

  DOI：

  10.1002/anie.201709659
• 作为产物：
  描述：

  (4aS,8aR)-4a-allyl-8a-methyl-5-methyleneoctahydro-1H-spiro[naphthalene-2,2'-[1,3]dioxolane] 在 对甲苯磺酸 作用下， 以 丙酮 为溶剂， 以12.78 g的产率得到(4aS,8aR)-8a-methyl-5-methylidene-4a-prop-2-enyl-1,3,4,6,7,8-hexahydronaphthalen-2-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

• Radical Cyclization of Alkene-Tethered Ketones Initiated by Hydrogen-Atom Transfer
  作者：Mar Saladrigas、Caroline Bosch、Gisela V. Saborit、Josep Bonjoch、Ben Bradshaw

  DOI：10.1002/anie.201709659

  日期：2018.1.2

  An unprecedented C−C coupling reaction between alkenes and ketones by hydrogen‐atom transfer, using Fe(acac)3 and PhSiH3 in EtOH, is described. This mild protocol features high site selectivity and allows the construction of sterically congested structures containing tertiary alcohols and quaternary centers. The overall process introduces a novel strategic bond disconnection for ring‐closing reactions

  描述了在EtOH中使用Fe（acac）3和PhSiH 3通过氢原子转移实现烯烃与酮之间前所未有的C-C偶联反应。这种温和的方案具有很高的位点选择性，并允许构建含有叔醇和季中心的空间拥挤结构。整个过程为开环反应引入了一种新颖的策略性键断开。
• 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.