4-(4-Methylphenyl)sulfonyl-4-azatetracyclo[9.2.1.02,10.03,7]tetradeca-2,5,7,9,12-pentaen-9-ol | 850888-80-1

• 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: 4-(4-Methylphenyl)sulfonyl-4-azatetracyclo[9.2.1.02,10.03,7]tetradeca-2,5,7,9,12-pentaen-9-ol
• CAS: 850888-80-1
• 化学式: C₂₀H₁₇NO₃S
• 分子量: 351.426
• InChiKey: LJLMGTATHGHFOG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.2
• 重原子数：
  25
• 可旋转键数：
  2
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  67.7
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  4-(4-Methylphenyl)sulfonyl-4-azatetracyclo[9.2.1.02,10.03,7]tetradeca-2,5,7,9,12-pentaen-9-ol 在 bis-triphenylphosphine-palladium(II) chloride 2,3,5-三甲基吡啶 、 sodium periodate 、 四氧化锇 、 N-甲基吲哚酮 、 2,6-二叔丁基-4-甲基苯酚 、 lithium chloride 作用下， 以 四氢呋喃 、 二氯甲烷 、 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 7.29h， 生成 Methanesulfonic acid (6S,8R)-5-((E)-but-1-enyl)-6-methanesulfonyloxymethyl-1-(toluene-4-sulfonyl)-1,6,7,8-tetrahydro-cyclopenta[g]indol-8-ylmethyl ester
  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 碘苯二乙酸 作用下， 以 二氯甲烷 为溶剂， 反应 3.0h， 生成 4-(4-Methylphenyl)sulfonyl-4-azatetracyclo[9.2.1.02,10.03,7]tetradeca-2,5,7,9,12-pentaen-9-ol
  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

文献信息

• Total Synthesis of (±)-Herbindole A, (±)-Herbindole B, and (±)-<i>cis</i>-Trikentrin A
  作者：Stephen K. Jackson、Michael A. Kerr

  DOI：10.1021/jo062350v

  日期：2007.2.1

  [GRAPHIC]Herein we describe a divergent total synthesis of the title compounds utilizing Diels-Alder reactions of monoimine quinoids, followed by cyclization of the aromatized adducts to generate the tricyclic skeletons. Elaboration to iodinated or triflated indole derivatives allows for installation of the requisite alkyl substitution via cross-coupling reactions.