1-(1-ethyl-1H-indole-2-yl)ethanone | 172840-56-1

• 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-(1-ethyl-1H-indole-2-yl)ethanone
• 英文别名: 1-(1-ethyl-1H-indol-2-yl)ethanone；1-(1-Ethylindol-2-yl)ethanone
• CAS: 172840-56-1
• 化学式: C₁₂H₁₃NO
• 分子量: 187.241
• InChiKey: ARUPMPPIUWFUTC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  14
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  22
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  1-(1-ethyl-1H-indole-2-yl)ethanone 在 sodium hydroxide 作用下， 以 甲醇 为溶剂， 反应 9.0h， 生成
  参考文献：
  名称：

  Design and Synthesis of Novel Indole β-Diketo Acid Derivatives as HIV-1 Integrase Inhibitors

  摘要：

  Diketo acids such as S-1360 (1A) and L-731,988 (2) are potent and selective inhibitors of HIV-1 integrase (IN). A plethora of diketo acid-containing compounds have been claimed in patent literature without disclosing much biological activities and synthetic details (reviewed in Neamati, N. Exp. Opin. Ther. Pat. 2002, 12, 709-724). To establish a coherent structure-activity relationship among the substituted indole nucleus bearing a beta-diketo acid moiety, a series of substituted indole-beta-diketo acids (4a-f and 5a-e) were synthesized. All compounds tested showed anti-IN activity at low micromolar concentrations with varied selectivity against the strand transfer process. Three compounds, the indole-3-beta-diketo acids 5a and 5c, and the parent ester 9c, have shown an antiviral activity in cell-based assays. We further confirmed a keto-enolic structure in the 2,3-position of the diketo acid moiety of a representative compound (4c) using NMR and X-ray crystallographic analysis. Using this structure as a lead for all of our computational studies, we found that the title compounds extensively interact with the essential amino acids on the active site of IN.

  DOI：

  10.1021/jm049944f
• 作为产物：
  描述：

  吲哚-2-羧酸乙酯 在 氢氧化钾 作用下， 以 乙醚 、 水 、 二甲基亚砜 为溶剂， 反应 6.0h， 生成 1-(1-ethyl-1H-indole-2-yl)ethanone
  参考文献：
  名称：

  Design and Synthesis of Novel Indole β-Diketo Acid Derivatives as HIV-1 Integrase Inhibitors

  摘要：

  Diketo acids such as S-1360 (1A) and L-731,988 (2) are potent and selective inhibitors of HIV-1 integrase (IN). A plethora of diketo acid-containing compounds have been claimed in patent literature without disclosing much biological activities and synthetic details (reviewed in Neamati, N. Exp. Opin. Ther. Pat. 2002, 12, 709-724). To establish a coherent structure-activity relationship among the substituted indole nucleus bearing a beta-diketo acid moiety, a series of substituted indole-beta-diketo acids (4a-f and 5a-e) were synthesized. All compounds tested showed anti-IN activity at low micromolar concentrations with varied selectivity against the strand transfer process. Three compounds, the indole-3-beta-diketo acids 5a and 5c, and the parent ester 9c, have shown an antiviral activity in cell-based assays. We further confirmed a keto-enolic structure in the 2,3-position of the diketo acid moiety of a representative compound (4c) using NMR and X-ray crystallographic analysis. Using this structure as a lead for all of our computational studies, we found that the title compounds extensively interact with the essential amino acids on the active site of IN.

  DOI：

  10.1021/jm049944f

文献信息

• An efficient synthesis of carbazoles from PtCl2-catalyzed cyclization of 1-(indol-2-yl)-2,3-allenols
  作者：Wangqing Kong、Chunling Fu、Shengming Ma

  DOI：10.1039/b909649c

  日期：——

  The PtCl2-catalyzed reaction of 1-(indol-2-yl)-2,3-allenols occurred smoothly to form carbazoles by connecting the 3-carbon atom of indole with the 4-carbon atom of the allenol moiety, referring to the carbon atom connected to the hydroxyl group.

  PtCl2催化的1-(吲哚-2-基)-2,3-烯醇反应顺利进行，通过将吲哚的3号碳原子与烯醇部分的4号碳原子连接，形成了卡巴唑，后者是指与羟基相连的碳原子。
• Studies on [PtCl₂]- or [AuCl]-Catalyzed Cyclization of 1-(Indol-2-yl)-2,3-Allenols: The Effects of Water/Steric Hindrance and 1,2-Migration Selectivity
  作者：Youai Qiu、Chunling Fu、Xue Zhang、Shengming Ma

  DOI：10.1002/chem.201402423

  日期：2014.8.11

  migration of the gold carbene intermediate was observed: compared with the methyl group, the isopropyl, cyclopropyl, cyclobutyl, and cyclohexyl groups migrate exclusively; the cyclopropyl group shifts selectively over the ethyl group; the 1,2‐migration of a non‐methyl linear alkyl is faster than methyl group; the phenyl group migrates exclusively over methyl or ethyl group. DFT calculations show that

  1-（吲哚-2-基）-2-3,3-烯醇的[PtCl 2 ]-或[AuCl]催化的反应在室温下平稳进行，从而有效地提供了一系列多取代的咔唑。与[PtCl 2 ]催化的方法相比，[AuCl]催化的反应在范围和选择性方面都取得了重大进展。观察到金卡宾中间体的选择性1,2-烷基或芳基迁移：与甲基相比，异丙基，环丙基，环丁基和环己基仅迁移；环丙基选择性地转移到乙基上；非甲基直链烷基的1,2-迁移比甲基快；苯基仅在甲基或乙基上迁移。DFT计算表明水消除了H2 O所需的能量要低得多，并且验证了观察到的不同烷基或苯基的迁移偏好。
• Exclusive 1,2-Aryl Shift in Platinum(II) Chloride-Catalyzed Cyclization of 1-(Indol-2-yl)-2,3-allenols
  作者：Wangqing Kong、Youai Qiu、Xue Zhang、Chunling Fu、Shengming Ma

  DOI：10.1002/adsc.201100935

  日期：2012.8.13

  An efficient cyclization of 1-(indole-2-yl)-2,3-allenols in the presence of platinum(II) chloride leading to polysubstituted carbazoles via 1,2-methyl or an exclusive 1,2-aryl migration of the metal-carbene intermediate was observed. The reaction proceeds via the intermediacy of a metal carbene intermediate, which induces the carbon-carbon bond cleavage via 1,2-migration to afford the products.

  1-（吲哚-2-基）-2,3-烯丙醇在氯化铂（II）的存在下有效环化，从而通过金属的1,2-甲基或排他的1,2-芳基迁移导致多取代的咔唑观察到-卡宾中间体。该反应通过金属卡宾中间体的中间体进行，该中间体通过1，2-迁移诱导碳-碳键裂解，得到产物。
• Ferrer, Pedro; Avendano, Carmen; Soellhuber, Monica, Liebigs Annalen, 1995, # 10, p. 1895 - 1900
  作者：Ferrer, Pedro、Avendano, Carmen、Soellhuber, Monica

  DOI：——

  日期：——