4-(indol-2-yl)but-3-en-2-one | 123217-72-1

• 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: 4-(indol-2-yl)but-3-en-2-one
• 英文别名: (Z)-4-(1H-Indol-2-yl)but-3-en-2-one
• CAS: 123217-72-1
• 化学式: C₁₂H₁₁NO
• 分子量: 185.225
• InChiKey: KOKGNUYOCCXQRV-SREVYHEPSA-N

物化性质

• 沸点：
  401.1±20.0 °C(Predicted)
• 密度：
  1.183±0.06 g/cm3(Predicted)

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：
  0.08
• 拓扑面积：
  32.9
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为产物：
  描述：

  1-乙酰吲哚 、 乙炔 、 alkaline earth salt of/the/ methylsulfuric acid 以 正庚烷 、 苯 为溶剂， 反应 3.5h， 以16%的产率得到4-(indol-2-yl)but-3-en-2-one
  参考文献：
  名称：

  Synthesis and alkyne-coupling chemistry of cyclomanganated 1- and 3-acetylindoles, 3-formylindole and analogues

  摘要：

  The syntheses are reported of new cyclomanganated indole derivatives (1-acetyl-kappa O-indolyl-kappa C-2)dicarbonylbis(trimethylphosphite)manganese (2), (1-methyl-3-acetyl-kappa O-indolyl-kappa C-2)tetracarbonylmanganese (4), (3-formyl-kappa O-indolyl-kappa C-2)tetracarbonylmanganese (5a) and (1-methyl-3-formyl-kappa O-indolyl-kappa C-2)tetracarbonylmanganese (5b). The unusually complicated crystal structure of 5b has been determined, the first for a cyclomanganated aryl aldehyde.The preparations of a mitomycin-related pyrrolo-indole and related products by thermally promoted and oxidatively (Me3NO) initiated alkyne-coupling reactions of the previously known complex (1-acetyl-kappa O-indolyl-kappa C-2)tetracarbonylmanganese (1) are reported for different alkynes and solvents. X-ray crystal structures are reported for the dimethyl acetylenedicarboxylate coupling product of 1 (dimethyl 1-methyl-1-hydroxypyrrolo[1,2a]-indole-2,3-dicarboxylate; 6a), and an unusually-cyclised triple insertion product 8 from the coupling of acetylene with 4, in which a cyclopentadiene moiety is eta(3)-allyl-coordinated to Mn through only one double bond and an exocyclic carbon, but which rearranges on heating to an eta(5)-cyclopentadienyl complex. (c) 2005 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.jorganchem.2005.09.049

文献信息

• Selective Wittig Reactions for the Synthesis of Variously Substituted 2-Vinylindoles
  作者：Manfred Eitel、Ulf Pindur

  DOI：10.1055/s-1989-27253

  日期：——

  Three selective variants of the Wittig reaction for the syntheses of 2-vinylindoles are described. The reactions are relatively easy to perform, exhibit E-selectivity, and are characterized by a good flexibility with regard to the functional groups present in the vinyl moiety.

  描述了三种选择性变体的威蒂格反应，用于合成2-乙烯基吲哚。这些反应相对容易进行，表现出E-选择性，并且在乙烯基部分的功能团方面具有良好的灵活性。
• EITEL, MANFRED;PINDUR, ULF, SUNTHESIS,(1989) N, C. 364-367
  作者：EITEL, MANFRED、PINDUR, ULF

  DOI：——

  日期：——
• Synthesis and alkyne-coupling chemistry of cyclomanganated 1- and 3-acetylindoles, 3-formylindole and analogues
  作者：Gary J. Depree、Lyndsay Main、Brian K. Nicholson、Nicholas P. Robinson、Geoffrey B. Jameson

  DOI：10.1016/j.jorganchem.2005.09.049

  日期：2006.2

  The syntheses are reported of new cyclomanganated indole derivatives (1-acetyl-kappa O-indolyl-kappa C-2)dicarbonylbis(trimethylphosphite)manganese (2), (1-methyl-3-acetyl-kappa O-indolyl-kappa C-2)tetracarbonylmanganese (4), (3-formyl-kappa O-indolyl-kappa C-2)tetracarbonylmanganese (5a) and (1-methyl-3-formyl-kappa O-indolyl-kappa C-2)tetracarbonylmanganese (5b). The unusually complicated crystal structure of 5b has been determined, the first for a cyclomanganated aryl aldehyde.The preparations of a mitomycin-related pyrrolo-indole and related products by thermally promoted and oxidatively (Me3NO) initiated alkyne-coupling reactions of the previously known complex (1-acetyl-kappa O-indolyl-kappa C-2)tetracarbonylmanganese (1) are reported for different alkynes and solvents. X-ray crystal structures are reported for the dimethyl acetylenedicarboxylate coupling product of 1 (dimethyl 1-methyl-1-hydroxypyrrolo[1,2a]-indole-2,3-dicarboxylate; 6a), and an unusually-cyclised triple insertion product 8 from the coupling of acetylene with 4, in which a cyclopentadiene moiety is eta(3)-allyl-coordinated to Mn through only one double bond and an exocyclic carbon, but which rearranges on heating to an eta(5)-cyclopentadienyl complex. (c) 2005 Elsevier B.V. All rights reserved.