Nominine | 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: Nominine
• 英文别名: (1R,4S,4aR,8S,8aR)-8-[(1H-indol-3-yl)methyl]-4,4a-dimethyl-7-methylene-8a-(4-methylpent-3-enyl)decahydronaphthalen-1-ol；(-)-anominine；(1R,4S,4aR,8S,8aR)-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-HBDSXALQSA-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：

  在 四丁基氟化铵 作用下， 以 四氢呋喃 为溶剂， 反应 16.0h， 以7 mg的产率得到Nominine
  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 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.