5-methoxy-1-phenylsulfonyl-3-hydroxymethyl-2-methylindole | 168326-86-1

• 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: 5-methoxy-1-phenylsulfonyl-3-hydroxymethyl-2-methylindole
• 英文别名: (1-Benzenesulfonyl-5-methoxy-2-methyl-1H-indol-3-yl)-methanol；[1-(benzenesulfonyl)-5-methoxy-2-methylindol-3-yl]methanol
• CAS: 168326-86-1
• 化学式: C₁₇H₁₇NO₄S
• 分子量: 331.392
• InChiKey: IYOACCSOXDYGGR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  23
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  76.9
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  5-methoxy-1-phenylsulfonyl-3-hydroxymethyl-2-methylindole 在 manganese(IV) oxide 、 N-溴代丁二酰亚胺(NBS) 、 过氧化氢苯甲酰 、 sodium hydride 作用下， 以 四氢呋喃 、 四氯化碳 、 二氯甲烷 为溶剂， 反应 11.0h， 生成 5-Methoxy-3-(β-carbethoxyvinyl)-1-(phenylsulfonyl)-2-<β'-(6'-nitropiperonyl)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-5-甲氧基-2-甲基吲哚-3-羧酸乙酯 在 lithium aluminium tetrahydride 作用下， 以 四氢呋喃 为溶剂， 反应 1.0h， 以95%的产率得到5-methoxy-1-phenylsulfonyl-3-hydroxymethyl-2-methylindole
  参考文献：
  名称：

  2 (或 3)-甲基吲哚衍生物与活性二氧化锰的异常氧化

  摘要：

  摘要 5-甲氧基-1-苯基磺酰基-2-甲基吲哚-3-醛(3) 与活性二氧化锰氧化成相应的吲哚-2,3-二醛(4) 和类似的反应。

  DOI：

  10.1080/00397919508015444

文献信息

• 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.
• Unusual Oxidation of 2 (or 3)-Methylindole Derivatives with Active Manganese Dioxide
  作者：Arasambattu K. Mohanakrishnan、Panayencheri C. Srinivasan

  DOI：10.1080/00397919508015444

  日期：1995.8

  Abstract Oxidation of 5-methoxy-1-phenylsulfonyl-2-methyl indole-3-aldehyde (3) with active manganese dioxide to the corresponding indole-2,3-dialdehyde (4) and similar reactions are reported.

  摘要 5-甲氧基-1-苯基磺酰基-2-甲基吲哚-3-醛(3) 与活性二氧化锰氧化成相应的吲哚-2,3-二醛(4) 和类似的反应。