12-(Benzenesulfonyl)-6α-methoxy-5aβ,6β,12aβ,12bβ-tetrahydro-12H-naphtho<2,3-a>carbazole-5,13-dione | 134924-11-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 蒽
• 英文名称: 12-(Benzenesulfonyl)-6α-methoxy-5aβ,6β,12aβ,12bβ-tetrahydro-12H-naphtho<2,3-a>carbazole-5,13-dione
• 英文别名: 6α-methoxy-12-(phenylsulfonyl)-5aβ,6β,12aβ,12bβ-tetrahydro-12H-naphtho<2,3-a>carbazol-5,13-dion；6α-methoxy-12-(phenylsulfonyl)-5aβ,6β,12aβ,12bβ-tetrahydro-12H-naphtho[2,3-a]carbazol-5,13-dion；(5aR,6S,12aS,12bS)-12-(benzenesulfonyl)-6-methoxy-5a,6,12a,12b-tetrahydronaphtho[3,2-a]carbazole-5,13-dione
• CAS: 134924-11-1
• 化学式: C₂₇H₂₁NO₅S
• 分子量: 471.533
• InChiKey: QMQGBXSTEWANNU-OJJQZRKESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  34
• 可旋转键数：
  3
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.19
• 拓扑面积：
  89.1
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  12-(Benzenesulfonyl)-6α-methoxy-5aβ,6β,12aβ,12bβ-tetrahydro-12H-naphtho<2,3-a>carbazole-5,13-dione 在 2,3-二氯-5,6-二氰基-1,4-苯醌 作用下， 以 甲苯 为溶剂， 反应 12.0h， 以39%的产率得到12-(Benzenesulfonyl)-12H-naphtho<2,3-a>carbazole-5,13-dione
  参考文献：
  名称：

  [a]-Anellierte Carbazole mit Antitumoraktivit�t: Synthese und Cytotoxizit�t

  摘要：

  The cycloadducts 3, 5, and 7, readily available from methoxy-substituted 3-vinylindoles 1 and 2, were dehydrogenated with DDQ to the coplanar [a]-anellated carbazoles 4, 6, and 8. Compound 4a, also characterized by X-ray structural analysis, shows significant cytotoxicity against K562 und RXF393 human tumor cell lines.

  DOI：

  10.1007/bf00807414
• 作为产物：
  描述：

  (E)-1-(Phenylsulfonyl)-3-(β-methoxyvinyl)indole 、 1,4-萘醌 以 乙醇 为溶剂， 反应 12.0h， 以86%的产率得到12-(Benzenesulfonyl)-6α-methoxy-5aβ,6β,12aβ,12bβ-tetrahydro-12H-naphtho<2,3-a>carbazole-5,13-dione
  参考文献：
  名称：

  New Diels-Alder reactions of (E/Z)-2'-methoxy-substituted 3-vinylindoles with carbo- and heterodienophiles: regio- and stereoselective access to [b]-annelated indoles and functionalized or [a]-annelated carbazoles

  摘要：

  The (E/Z)-2'-methoxy-substituted 3-vinylindoles 1a,b react with some carbo- and azodienophiles to furnish new carbazoles and pyridazinoindoles. The conservation of the E and Z stereochemistry of 1 in these Diels-Alder reactions was investigated, and a mechanistic rationalization is given for the stereoselective and regioselective results observed.

  DOI：

  10.1021/jo00029a023

文献信息

• Diels-Alder-Reaktionen von Vinylindolen mit Arin und 1,4-Benzochinonen: Neue potentielle DNA-Interkalatoren
  作者：Ulf Pindur、Ludwig Pfeuffer、Manfred Eitel、Martina Rogge、Manfred Haber

  DOI：10.1007/bf00810830

  日期：1991.4

  Diels-Alder reactions of 2- and 3-vinylindoles with aryne, 1,4-benzo- and 1,4-naphthoquinone lead to new six-ring annellated carbazoles. Molecular modeling studies predict that the compounds with coplanar framework are able to intercalate with the B-DNA.
• [a]-Anellierte Carbazole mit Antitumoraktivit�t: Synthese und Cytotoxizit�t
  作者：M. Rogge、G. Fischer、U. Pindur、D. Schollmeyer

  DOI：10.1007/bf00807414

  日期：1996.1

  The cycloadducts 3, 5, and 7, readily available from methoxy-substituted 3-vinylindoles 1 and 2, were dehydrogenated with DDQ to the coplanar [a]-anellated carbazoles 4, 6, and 8. Compound 4a, also characterized by X-ray structural analysis, shows significant cytotoxicity against K562 und RXF393 human tumor cell lines.
• New Diels-Alder reactions of (E/Z)-2'-methoxy-substituted 3-vinylindoles with carbo- and heterodienophiles: regio- and stereoselective access to [b]-annelated indoles and functionalized or [a]-annelated carbazoles
  作者：Ulf Pindur、Myung Hwa Kim、Martina Rogge、Werner Massa、Michel Molinier

  DOI：10.1021/jo00029a023

  日期：1992.1

  The (E/Z)-2'-methoxy-substituted 3-vinylindoles 1a,b react with some carbo- and azodienophiles to furnish new carbazoles and pyridazinoindoles. The conservation of the E and Z stereochemistry of 1 in these Diels-Alder reactions was investigated, and a mechanistic rationalization is given for the stereoselective and regioselective results observed.