(2R,3aS,6R,6aS,10R,10aS)-2-ethoxy-10-(hydroxymethyl)-6,6a-dimethyl-2,3a,4,5,6,7,8,10-octahydro-1H-benzo[d][1]benzofuran-9-one | 1374409-86-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 氧烷类
• 英文名称: (2R,3aS,6R,6aS,10R,10aS)-2-ethoxy-10-(hydroxymethyl)-6,6a-dimethyl-2,3a,4,5,6,7,8,10-octahydro-1H-benzo[d][1]benzofuran-9-one
• CAS: 1374409-86-5
• 化学式: C₁₇H₂₈O₄
• 分子量: 296.407
• InChiKey: ODTGKXINDIZWSV-UMKNANMMSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  21
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.94
• 拓扑面积：
  55.8
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (2R,3aS,6R,6aS,10R,10aS)-2-ethoxy-10-(hydroxymethyl)-6,6a-dimethyl-2,3a,4,5,6,7,8,10-octahydro-1H-benzo[d][1]benzofuran-9-one 在 咪唑 、 正丁基锂 、 四丁基氟化铵 、 戴斯-马丁氧化剂 作用下， 以 四氢呋喃 、 hexanes 、 乙醚 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 3.5h， 生成 (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
  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
• 作为产物：
  描述：

  在 偶氮二异丁腈 、 水 、 三正丁基氢锡 、 lithium hexamethyldisilazane 、 scandium tris(trifluoromethanesulfonate) 作用下， 以 四氢呋喃 、 甲苯 为溶剂， 生成 (2R,3aS,6R,6aS,10R,10aS)-2-ethoxy-10-(hydroxymethyl)-6,6a-dimethyl-2,3a,4,5,6,7,8,10-octahydro-1H-benzo[d][1]benzofuran-9-one
  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