2-(2-oxo-2-phenylethyl)-1H-indole-3-carbaldehyde | 1350934-42-7

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2-(2-oxo-2-phenylethyl)-1H-indole-3-carbaldehyde
• 英文别名: 2-phenacyl-1H-indole-3-carbaldehyde
• CAS: 1350934-42-7
• 化学式: C₁₇H₁₃NO₂
• 分子量: 263.296
• InChiKey: UDYYRACJDUTGOT-UHFFFAOYSA-N

物化性质

• 沸点：
  499.7±30.0 °C(Predicted)
• 密度：
  1.279±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  20
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.06
• 拓扑面积：
  49.9
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  2-(2-oxo-2-phenylethyl)-1H-indole-3-carbaldehyde 在 ammonium acetate 作用下， 以 1,4-二氧六环 为溶剂， 反应 2.0h， 以92.7 mg的产率得到3-phenyl-5H-pyrido[4,3-b]indole
  参考文献：
  名称：

  Metal-Free Carbonyl-Assisted Regioselective Hydration of Alkynes: An Access to Dicarbonyls

  摘要：

  Metal-free regioselective hydration of o-alkynylaldehydes with the assistance of neighboring carbonyl oxygen is disclosed. The developed protocol provides a facile route to synthesize a series of multisubstituted carbonyl containing scaffolds that enable the potential application toward the synthesis of highly diversified 5-azaindoles. gamma-Carbolines and 2,8-diazacarbazoles can also be accessed directly without isolating the dicarbonyl compounds. The developed methodology is operationally simple and environment-friendly, tolerates a wide variety of functional groups, and is applicable toward large scale synthesis.

  DOI：

  10.1021/acs.orglett.9b01649
• 作为产物：
  描述：

  苯乙炔 在 水 、 三乙胺 、 三苯基膦 、 palladium dichloride 作用下， 以 1,4-二氧六环 、 乙腈 为溶剂， 反应 6.0h， 生成 2-(2-oxo-2-phenylethyl)-1H-indole-3-carbaldehyde
  参考文献：
  名称：

  Metal-Free Carbonyl-Assisted Regioselective Hydration of Alkynes: An Access to Dicarbonyls

  摘要：

  Metal-free regioselective hydration of o-alkynylaldehydes with the assistance of neighboring carbonyl oxygen is disclosed. The developed protocol provides a facile route to synthesize a series of multisubstituted carbonyl containing scaffolds that enable the potential application toward the synthesis of highly diversified 5-azaindoles. gamma-Carbolines and 2,8-diazacarbazoles can also be accessed directly without isolating the dicarbonyl compounds. The developed methodology is operationally simple and environment-friendly, tolerates a wide variety of functional groups, and is applicable toward large scale synthesis.

  DOI：

  10.1021/acs.orglett.9b01649

文献信息

• A catalyst-free, efficient green MCR protocol for access to functionalized γ-carbolines in water
  作者：Anuradha Dagar、Soumen Biswas、Sampak Samanta

  DOI：10.1039/c5ra08422a

  日期：——

  functionalized γ-carboline derivatives has been successfully realized in water through a one-pot three-component reaction involving several aryl/hetero-aryl/alkyl/alkenyl/alkynyl/ferrocenyl aldehydes, 3-formyl indole derivatives and ammonium acetate as a cheap N-source. The most important feature of the current methodology is that this hetero-annulation reaction of indole to γ-carboline can occur in good

  通过涉及几个芳基/杂芳基/烷基/烯基/炔基/二茂铁基醛的一锅三组分反应，已经成功地在水中实现了构建官能化γ-咔啉衍生物的通用，温和，有效和实用的方法， 3-甲酰基吲哚衍生物和乙酸铵作为廉价的N源。当前方法学的最重要特征是，从室温下无催化剂和氧化剂的廉价廉价原料开始，吲哚与γ-咔啉的杂环化反应可以在室温下以较宽的底物范围以良好至极好的收率发生。无条件。此外，通过我们的方法，已经可以轻松获得五环喹啉酮稠合的咔啉衍生物。
• Novel Synthetic Method of 2-(2-Oxoethyl)-1H-indole-3-carbaldehydes
  作者：Inga Cikotiene、Rita Buksnaitiene

  DOI：10.1055/s-0030-1260317

  日期：2011.10

  The smooth and regioselective synthesis of 2-(2-oxo­ethyl)-1H-indole-3-carbaldehydes via silver-catalyzed 6-endo-dig acetalization-cyclization reaction followed by immediate hydrolysis of the unstable 1-alkoxypyrano[4,3-b]indole intermediates is described.

  本文报道了通过银催化的6-endo-dig缩酮化-环化反应，合成2-(2-氧代乙基)-1H-吲哚-3-甲醛，随后立即水解不稳定的1-烷氧基吡喃并[4,3-b]吲哚中间体的过程。
• Access to Substituted Carbazoles in Water by a One-Pot Sequential Reaction of α,β-Substituted Nitro Olefins with 2-(3-Formyl-1<i>H</i>-indol-2-yl)acetates
  作者：Soumen Biswas、Anuradha Dagar、Anvita Srivastava、Sampak Samanta

  DOI：10.1002/ejoc.201500470

  日期：2015.7

  interesting new multifunctional carbazole scaffolds have been prepared in good to excellent yields by an organocatalytic one-pot two-step sequential reaction between α-alkyl-β-substituted nitro olefins or α-alkyl-δ-substituted nitro-dienes and 2-(3-formyl-1H-indol-2-yl)acetates in water at room temperature followed by treatment with 2 n HCl under mild conditions. This one-pot, organocatalytic, oxidant-free

  通过α-烷基-β-取代硝基烯烃或α-烷基-δ-取代硝基二烯与2 -(3-formyl-1H-indol-2-yl)acetates 在室温下的水中，然后在温和条件下用 2n HCl 处理。这种一锅法、有机催化、无氧化剂、温和且环保的工艺可以提供一种强大的替代合成方案，以快速获得与生物活性天然咔唑结构相似的 3-烷基取代咔唑骨架。此外，使用这种合成方法已经有效地制备了具有生物学意义的环状酰亚胺和喹啉酮稠合咔唑。