1-tosyl-6,9-dihydro-1H-6,9-methanobenzo[g]indol-5-yl trifluoromethanesulfonate | 850888-99-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 1-tosyl-6,9-dihydro-1H-6,9-methanobenzo[g]indol-5-yl trifluoromethanesulfonate
• CAS: 850888-99-2
• 化学式: C₂₁H₁₆F₃NO₅S₂
• 分子量: 483.489
• InChiKey: XOURNCUBALVUEZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.56
• 重原子数：
  32.0
• 可旋转键数：
  4.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.24
• 拓扑面积：
  82.44
• 氢给体数：
  0.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  1-tosyl-6,9-dihydro-1H-6,9-methanobenzo[g]indol-5-yl trifluoromethanesulfonate 在 四氧化锇 、 N-甲基吲哚酮 作用下， 以 四氢呋喃 、 水 为溶剂， 反应 1.0h， 以90%的产率得到[12,13-Dihydroxy-4-(4-methylphenyl)sulfonyl-4-azatetracyclo[9.2.1.02,10.03,7]tetradeca-2,5,7,9-tetraen-9-yl] trifluoromethanesulfonate
  参考文献：
  名称：

  Total Synthesis of (±)-Herbindole B and (±)-cis-Trikentrin B

  摘要：

  Herbindole B and cis-trikentrin B are naturally occurring indoles having the unusual and synthetically challenging pattern of carbon substitution at the 4-7 and 5-7 positions, respectively, with no substitution at the 1-3 positions. The total syntheses of these polyalkylated indoles have been achieved in 19 and 12 steps, respectively. The synthesis of herbindole B relies on two iterations of a quinine monoimine Diels-Alder reaction, while cis-trikentrin B uses a single cycloaddition of a suitable quinone monolmine. Indolization of the adducts provides suitably substituted benzopyrrole nuclei for elaboration to the natural products.

  DOI：

  10.1021/ol047498k
• 作为产物：
  描述：

  N-[2-(2,2-Dimethoxy-ethyl)-4-hydroxy-phenyl]-4-methyl-benzenesulfonamide 在 2,3,5-三甲基吡啶 、 碘苯二乙酸 作用下， 以 二氯甲烷 为溶剂， 反应 3.0h， 生成 1-tosyl-6,9-dihydro-1H-6,9-methanobenzo[g]indol-5-yl trifluoromethanesulfonate
  参考文献：
  名称：

  Total Synthesis of (±)-Herbindole B and (±)-cis-Trikentrin B

  摘要：

  Herbindole B and cis-trikentrin B are naturally occurring indoles having the unusual and synthetically challenging pattern of carbon substitution at the 4-7 and 5-7 positions, respectively, with no substitution at the 1-3 positions. The total syntheses of these polyalkylated indoles have been achieved in 19 and 12 steps, respectively. The synthesis of herbindole B relies on two iterations of a quinine monoimine Diels-Alder reaction, while cis-trikentrin B uses a single cycloaddition of a suitable quinone monolmine. Indolization of the adducts provides suitably substituted benzopyrrole nuclei for elaboration to the natural products.

  DOI：

  10.1021/ol047498k