1,7-dihydroxy-3-methyl-5-methylphenyl-5H-benz[b]carbazole-6,11-dione | 139932-93-7

• 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: 1,7-dihydroxy-3-methyl-5-methylphenyl-5H-benz[b]carbazole-6,11-dione
• CAS: 139932-93-7
• 化学式: C₂₄H₁₇NO₄
• 分子量: 383.403
• InChiKey: BMMYAIDMTIXIHM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.18
• 重原子数：
  29.0
• 可旋转键数：
  2.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.08
• 拓扑面积：
  79.53
• 氢给体数：
  2.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  1,7-dihydroxy-3-methyl-5-methylphenyl-5H-benz[b]carbazole-6,11-dione 、 碘甲烷 在 sodium hydroxide 、 苄基三甲基氯化铵 作用下， 以 二氯甲烷 、 水 为溶剂， 反应 48.0h， 生成 1,7-dimethoxy-3-methyl-5-methylphenyl-5H-benzo[b]carbazole-6,11-dione
  参考文献：
  名称：

  Synthesis of benzo[b]carbazoloquinones by coupling of organostannanes with bromoquinones

  摘要：

  The synthesis of 5-carbonitrile-1,7-dihydroxy-3-methyl-5H-benzo[b]carbazole-6,11-dione, the quinone originally proposed as prekinamycin, was completed by using a palladium and copper catalyzed Stille reaction as the key step. A subsequent heterocyclization afforded a mixture of para(benzo[b]carbazole-6,11-dione) and ortho (benzo[a]carbazole-6,11-dione) quinones. A procedure for the N-cyanation of model indoles is also described. (C) 1997 Elsevier Science Ltd.

  DOI：

  10.1016/s0040-4020(97)10085-0
• 作为产物：
  描述：

  2-bromo-5-methoxy-[1,4]naphthoquinone 在 四(三苯基膦)钯 、 三溴化硼 、 copper(I) bromide 作用下， 以 1,4-二氧六环 、 二氯甲烷 为溶剂， 反应 1.0h， 生成 1,7-dihydroxy-3-methyl-5-methylphenyl-5H-benz[b]carbazole-6,11-dione
  参考文献：
  名称：

  Synthesis of benzo[b]carbazoloquinones by coupling of organostannanes with bromoquinones

  摘要：

  The synthesis of 5-carbonitrile-1,7-dihydroxy-3-methyl-5H-benzo[b]carbazole-6,11-dione, the quinone originally proposed as prekinamycin, was completed by using a palladium and copper catalyzed Stille reaction as the key step. A subsequent heterocyclization afforded a mixture of para(benzo[b]carbazole-6,11-dione) and ortho (benzo[a]carbazole-6,11-dione) quinones. A procedure for the N-cyanation of model indoles is also described. (C) 1997 Elsevier Science Ltd.

  DOI：

  10.1016/s0040-4020(97)10085-0

文献信息

• Regioselective synthesis of the kinamycin ABCD ring system
  作者：Patrick J. O'Sullivan、Rafael Moreno、William S. Murphy

  DOI：10.1016/s0040-4039(00)93989-3

  日期：1992.1

  The new bromoquinone-enamine annulation was successfully extended to acyclic enamino ketones resulting in a new synthesis of the ABC framework 6 of kinamycins and when applied to cyclic enamino ketones 8a–e the first synthesis of their ABCD ring system. Smooth aromatisation of compounds 4b,d to 9a,b respectively was effected with DDQ.

  新的溴醌-烯胺环化成功地扩展到了无环烯胺酮，从而产生了新的kinamycin ABC构架6的合成，当应用于环状烯胺酮8a-e时，它们的ABCD环系统也首次合成。用DDQ分别实现化合物4b，d至9a，b的平滑芳构化。