(1R,4aR,5S,8R,8aR)-1-[(1H-indol-3-yl)methyl]-8a-(3-hydroxypropyl)-4a,5-dimethyl-8-(triethylsilyloxy)octahydro-1H-naphthalen-2-one | 1224845-50-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吲哚及其衍生物
• 英文名称: (1R,4aR,5S,8R,8aR)-1-[(1H-indol-3-yl)methyl]-8a-(3-hydroxypropyl)-4a,5-dimethyl-8-(triethylsilyloxy)octahydro-1H-naphthalen-2-one
• 英文别名: (1R,4aR,5S,8R,8aR)-8a-(3-hydroxypropyl)-1-(1H-indol-3-ylmethyl)-4a,5-dimethyl-8-triethylsilyloxy-3,4,5,6,7,8-hexahydro-1H-naphthalen-2-one
• CAS: 1224845-50-4
• 化学式: C₃₀H₄₇NO₃Si
• 分子量: 497.794
• InChiKey: WEVBFHHCLZPGNG-URPBTUBFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.28
• 重原子数：
  35
• 可旋转键数：
  10
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.7
• 拓扑面积：
  62.3
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (1R,4aR,5S,8R,8aR)-1-[(1H-indol-3-yl)methyl]-8a-(3-hydroxypropyl)-4a,5-dimethyl-8-(triethylsilyloxy)octahydro-1H-naphthalen-2-one 在 四丙基高钌酸铵 、 N-甲基吗啉氧化物 作用下， 以 二氯甲烷 为溶剂， 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：

  3-((1S,4R,4aR,8aR)-5-((1H-indol-3-yl)methyl)-1,8a-dimethyl-6-oxo-4-((triethylsilyl)oxy)octahydronaphthalen-4a(2H)-yl)propyl acetate 在 potassium fluoride 、 乙醇 作用下， 反应 72.0h， 以63 mg的产率得到(1R,4aR,5S,8R,8aR)-1-[(1H-indol-3-yl)methyl]-8a-(3-hydroxypropyl)-4a,5-dimethyl-8-(triethylsilyloxy)octahydro-1H-naphthalen-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

• 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.