Diethyl <<1-(phenylsulfonyl)-2-(β-carbethoxyvinyl)indol-3-yl>methyl>phosphonate | 1026929-37-2

• 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: Diethyl <<1-(phenylsulfonyl)-2-(β-carbethoxyvinyl)indol-3-yl>methyl>phosphonate
• 英文别名: ethyl (E)-3-[1-(benzenesulfonyl)-3-(diethoxyphosphorylmethyl)indol-2-yl]prop-2-enoate
• CAS: 1026929-37-2
• 化学式: C₂₄H₂₈NO₇PS
• 分子量: 505.529
• InChiKey: HPPDMVHRKXETIH-WUKNDPDISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  34
• 可旋转键数：
  12
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  109
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  6-硝基藜芦醛 、 Diethyl <<1-(phenylsulfonyl)-2-(β-carbethoxyvinyl)indol-3-yl>methyl>phosphonate 在 正丁基锂 作用下， 以 四氢呋喃 为溶剂， 反应 2.0h， 以84%的产率得到2-(β-Carbethoxyvinyl)-1-(phenylsulfonyl)-3-<β'-(6'-nitroveratryl)vinyl>indole
  参考文献：
  名称：

  A Versatile Construction of the 8H-Quino[4,3-b]carbazole Ring System as a Potential DNA Binder

  摘要：

  A short synthesis of the quino[4,3-b]- and quino[3,4-b]carbazoles is reported. The key step of the synthesis involves the preparation of suitable 2,3-divinylindoles by consecutive Wittig reactions. The thermal electrocyclic reaction of the divinylindole with concomitant dehydrogenation in the presence of Pd-C gave the (nitroaryl)carbazole which on reductive cyclization led to the quinocarbazole. The cleavage of the phenylsulfonyl group followed by phosphorus oxychloride treatment and subsequent displacement of the chlorine with 3-(dimethylamino)-1-propylamine gave the title compound in 25% overall yield.

  DOI：

  10.1021/jo00112a011
• 作为产物：
  描述：

  1-(苯磺酰基)-3-甲基吲哚-2-甲醛 在 N-溴代丁二酰亚胺(NBS) 、 过氧化氢苯甲酰 作用下， 以 四氢呋喃 、 四氯化碳 为溶剂， 生成 Diethyl <<1-(phenylsulfonyl)-2-(β-carbethoxyvinyl)indol-3-yl>methyl>phosphonate
  参考文献：
  名称：

  A Versatile Construction of the 8H-Quino[4,3-b]carbazole Ring System as a Potential DNA Binder

  摘要：

  A short synthesis of the quino[4,3-b]- and quino[3,4-b]carbazoles is reported. The key step of the synthesis involves the preparation of suitable 2,3-divinylindoles by consecutive Wittig reactions. The thermal electrocyclic reaction of the divinylindole with concomitant dehydrogenation in the presence of Pd-C gave the (nitroaryl)carbazole which on reductive cyclization led to the quinocarbazole. The cleavage of the phenylsulfonyl group followed by phosphorus oxychloride treatment and subsequent displacement of the chlorine with 3-(dimethylamino)-1-propylamine gave the title compound in 25% overall yield.

  DOI：

  10.1021/jo00112a011

文献信息

• Synthetic Studies on Indolocarbazoles: A Facile Synthesis of Staurosporinone Analogues
  作者：Potharaju Raju、Ganesan Gobi Rajeshwaran、Arasambattu K. Mohanakrishnan

  DOI：10.1002/ejoc.201500939

  日期：2015.11

  Synthesis of indolocarbazoles was achieved through thermal electrocyclization followed by triethyl phosphite-mediated nitrene insertion reactions. Total synthesis of staurosporinone analogues was achieved from commercially available 2-methylindole. The CDK5/p25 kinase inhibition potential of some representative staurosporinone analogues was explored by using the TRFRET kinase assay.

  通过热电环化和亚磷酸三乙酯介导的氮烯插入反应合成吲哚并咔唑。staurosporinone 类似物的全合成是从市售的 2-甲基吲哚中实现的。通过使用 TRFRET 激酶测定探索了一些代表性星形孢菌素类似物的 CDK5/p25 激酶抑制潜力。
• A Versatile Construction of the 8H-Quino[4,3-b]carbazole Ring System as a Potential DNA Binder
  作者：Arasambattu K. Mohanakrishnan、Panayencheri C. Srinivasan

  DOI：10.1021/jo00112a011

  日期：1995.4

  A short synthesis of the quino[4,3-b]- and quino[3,4-b]carbazoles is reported. The key step of the synthesis involves the preparation of suitable 2,3-divinylindoles by consecutive Wittig reactions. The thermal electrocyclic reaction of the divinylindole with concomitant dehydrogenation in the presence of Pd-C gave the (nitroaryl)carbazole which on reductive cyclization led to the quinocarbazole. The cleavage of the phenylsulfonyl group followed by phosphorus oxychloride treatment and subsequent displacement of the chlorine with 3-(dimethylamino)-1-propylamine gave the title compound in 25% overall yield.