(+)-anominine | 120991-21-1

• 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: (+)-anominine
• 英文别名: anominine；nominine；(1S,4R,4aS,8R,8aS)-8-(1H-indol-3-ylmethyl)-4,4a-dimethyl-7-methylidene-8a-(4-methylpent-3-enyl)-2,3,4,5,6,8-hexahydro-1H-naphthalen-1-ol
• CAS: 120991-21-1
• 化学式: C₂₈H₃₉NO
• 分子量: 405.624
• InChiKey: BSSPRCKKWJRAJZ-LSKARBNJSA-N

物化性质

• 沸点：
  543.6±33.0 °C(Predicted)
• 密度：
  1.06±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  7.2
• 重原子数：
  30
• 可旋转键数：
  5
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.57
• 拓扑面积：
  36
• 氢给体数：
  2
• 氢受体数：
  1

反应信息

• 作为产物：
  描述：

  (R)-[(2R,3aS,6R,6aS,10R,10aS)-2-ethoxy-6,6a-dimethyl-9-methylidene-2,3a,4,5,6,7,8,10-octahydro-1H-benzo[d][1]benzofuran-10-yl]-[1-(benzenesulfonyl)indol-3-yl]methanol 在 4-二甲氨基吡啶 、 四(三苯基膦)钯 、 高氯酸 、 Hoveyda-Grubbs catalyst second generation 、 偶氮二异丁腈 、 四丁基氟化铵 、 三正丁基氢锡 、 甲酸铵 、 双(三甲基硅烷基)氨基钾 、 二异丁基氢化铝 、 三乙胺 作用下， 以 四氢呋喃 、 hexanes 、 二氯甲烷 、 水 、 甲苯 为溶剂， 反应 15.17h， 生成 (+)-anominine
  参考文献：
  名称：

  Total Syntheses of Anominine and Tubingensin A

  摘要：

  A divergent strategy for the total syntheses of the indole terpenoid anominine (1) and its natural congener tubingensin A (2) has been developed. The common intermediate 11 bearing all of the required stereogenic centers for both natural products was first assembled by employing a Ueno-Stork radical cyclization and a Sc(OTf)(3)-mediated Mukaiyama aldol reaction to form the key C-C bonds in a stereocontrolled manner. The route to anominine features a radical deoxygenation followed by an efficient side-chain installation, while the path to tubingensin A exploits a CuOTf-promoted 6 pi-electrocyclization/aromatization sequence to forge the central region of the pentacyclic scaffold.

  DOI：

  10.1021/ja302765m

文献信息

• Total Syntheses of Anominine and Tubingensin A
  作者：Ming Bian、Zhen Wang、Xiaochun Xiong、Yu Sun、Carlo Matera、K. C. Nicolaou、Ang Li

  DOI：10.1021/ja302765m

  日期：2012.5.16

  A divergent strategy for the total syntheses of the indole terpenoid anominine (1) and its natural congener tubingensin A (2) has been developed. The common intermediate 11 bearing all of the required stereogenic centers for both natural products was first assembled by employing a Ueno-Stork radical cyclization and a Sc(OTf)(3)-mediated Mukaiyama aldol reaction to form the key C-C bonds in a stereocontrolled manner. The route to anominine features a radical deoxygenation followed by an efficient side-chain installation, while the path to tubingensin A exploits a CuOTf-promoted 6 pi-electrocyclization/aromatization sequence to forge the central region of the pentacyclic scaffold.