2-cyano-6-methylsulfonyl-3-methylcarbonatomethylindole | 706790-13-8

• 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: 2-cyano-6-methylsulfonyl-3-methylcarbonatomethylindole
• 英文别名: (2-cyano-6-methylsulfonyl-1H-indol-3-yl)methyl methyl carbonate
• CAS: 706790-13-8
• 化学式: C₁₃H₁₂N₂O₅S
• 分子量: 308.315
• InChiKey: NZHGOWVXEIJPOZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  21
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.23
• 拓扑面积：
  118
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  碘苯 、 2-cyano-6-methylsulfonyl-3-methylcarbonatomethylindole 在 magnesium 、 zinc(II) chloride 、 四(三苯基膦)钯 作用下， 以 四氢呋喃 为溶剂， 生成 3-benzyl-6-methylsulfonyl-1H-indole-2-carbonitrile
  参考文献：
  名称：

  Preparation of 3-arylmethylindoles as selective COX-2 inhibitors

  摘要：

  The 3-arylmethylation of indoles using TMSOTf/Et3SiH with a wide variety of substituted benzaldehydes has been accomplished. Under these mild Lewis acid mediated reductive conditions, it was demonstrated that indoles bearing both 6-MeSO2, and 2-methyl substituents could be 3-arylmethylated in good to excellent yields to afford the corresponding 3-arylmethyl indoles, effective as selective COX-2 inhibitors. I it addition, the viability of this method for the reductive alkylation of indoles by ketones was demonstrated and shown to be C-3 regioselective. For indoles bearing both a 6-MeSO2, and 2-cyano substituent where this indole reductive alkylation methodology was unsuccessful, all unprecedented Pd(0) mediated arylorganozinc Coupling With the requisite Substituted 3-methylcarbonatomethylindole proved Successful in affording the desired 2-cyano-6-MeSO2-3-arylmethylindoles effective as selective COX-2 inhibitors. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2004.03.068
• 作为产物：
  描述：

  3-formyl-6-methylsulfonyl-1H-indole-2-carbonitrile 在 sodium tetrahydroborate 、 三乙胺 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 生成 2-cyano-6-methylsulfonyl-3-methylcarbonatomethylindole
  参考文献：
  名称：

  Preparation of 3-arylmethylindoles as selective COX-2 inhibitors

  摘要：

  The 3-arylmethylation of indoles using TMSOTf/Et3SiH with a wide variety of substituted benzaldehydes has been accomplished. Under these mild Lewis acid mediated reductive conditions, it was demonstrated that indoles bearing both 6-MeSO2, and 2-methyl substituents could be 3-arylmethylated in good to excellent yields to afford the corresponding 3-arylmethyl indoles, effective as selective COX-2 inhibitors. I it addition, the viability of this method for the reductive alkylation of indoles by ketones was demonstrated and shown to be C-3 regioselective. For indoles bearing both a 6-MeSO2, and 2-cyano substituent where this indole reductive alkylation methodology was unsuccessful, all unprecedented Pd(0) mediated arylorganozinc Coupling With the requisite Substituted 3-methylcarbonatomethylindole proved Successful in affording the desired 2-cyano-6-MeSO2-3-arylmethylindoles effective as selective COX-2 inhibitors. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2004.03.068

文献信息

• Preparation of 3-arylmethylindoles as selective COX-2 inhibitors
  作者：Jeffrey A Campbell、Viola Bordunov、Chris A Broka、John Dankwardt、Robert T Hendricks、James M Kress、Keith A.M Walker、Jin-Hai Wang

  DOI：10.1016/j.tetlet.2004.03.068

  日期：2004.5

  The 3-arylmethylation of indoles using TMSOTf/Et3SiH with a wide variety of substituted benzaldehydes has been accomplished. Under these mild Lewis acid mediated reductive conditions, it was demonstrated that indoles bearing both 6-MeSO2, and 2-methyl substituents could be 3-arylmethylated in good to excellent yields to afford the corresponding 3-arylmethyl indoles, effective as selective COX-2 inhibitors. I it addition, the viability of this method for the reductive alkylation of indoles by ketones was demonstrated and shown to be C-3 regioselective. For indoles bearing both a 6-MeSO2, and 2-cyano substituent where this indole reductive alkylation methodology was unsuccessful, all unprecedented Pd(0) mediated arylorganozinc Coupling With the requisite Substituted 3-methylcarbonatomethylindole proved Successful in affording the desired 2-cyano-6-MeSO2-3-arylmethylindoles effective as selective COX-2 inhibitors. (C) 2004 Elsevier Ltd. All rights reserved.