4-(4-fluorophenyl)-4-oxobutanal | 84819-46-5

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 4-(4-fluorophenyl)-4-oxobutanal
• CAS: 84819-46-5
• 化学式: C₁₀H₉FO₂
• 分子量: 180.179
• InChiKey: IUPCCVUTZAKOGW-UHFFFAOYSA-N

物化性质

• 沸点：
  302.4±22.0 °C(Predicted)
• 密度：
  1.158±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.1
• 重原子数：
  13
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  34.1
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  4-(4-fluorophenyl)-4-oxobutanal 在 N-溴代丁二酰亚胺(NBS) 作用下， 以 二甲基亚砜 、 乙腈 为溶剂， 反应 30.0h， 生成 C₂₅H₁₆BrFN₂O₂
  参考文献：
  名称：

  Sequential multicomponent catalytic synthesis of pyrrole-3-carboxaldehydes: evaluation of antibacterial and antifungal activities along with docking studies

  摘要：

  开发了一种顺序多组分方法，用于合成高度取代的N-芳基吡咯-3-甲醛，并针对细菌菌株进行抗菌和抗真菌活性测试。

  DOI：

  10.1039/d0nj03575k
• 作为产物：
  描述：

  3-(1,3-dioxolan-2-yl)-1-(4-fluorophenyl)propan-1-one 在 盐酸 作用下， 生成 4-(4-fluorophenyl)-4-oxobutanal
  参考文献：
  名称：

  Kruse, Chris G.; Bouw, Jan P.; Hes, Roelof van, Heterocycles, 1987, vol. 26, # 12, p. 3141 - 3151

  摘要：

  DOI：

文献信息

• Organocatalytic Redox Isomerization of Electron-Deficient Allylic Alcohols: Synthesis of 1,4-Ketoaldehydes
  作者：Keshab Mondal、Buddhadeb Mondal、Subhas Chandra Pan

  DOI：10.1021/acs.joc.6b00243

  日期：2016.6.3

  An organocatalytic redox isomerization strategy has been developed for the synthesis of 1,4-ketoaldehydes. DABCO was found to be the best catalyst for the isomerization of γ-hydroxy enones. With 20 mol % of DABCO as catalyst and DMSO as the solvent high yields have been achieved for different 1,4-ketoaldehydes.

  已经开发了用于合成1，4-酮醛的有机催化氧化还原异构化策略。发现DABCO是γ-羟基烯酮异构化的最佳催化剂。用20mol％的DABCO作为催化剂和DMSO作为溶剂，对于不同的1，4-酮醛已经实现了高收率。
• Copper-Catalyzed Alkylation of Nitroalkanes with α-Bromonitriles: Synthesis of β-Cyanonitroalkanes
  作者：Kirk W. Shimkin、Peter G. Gildner、Donald A. Watson

  DOI：10.1021/acs.orglett.6b00093

  日期：2016.3.4

  Copper catalysis now enables the efficient C-alkylation of nitroalkanes with α-bromonitriles. Using a simple and inexpensive catalyst, this process provides access to β-cyanonitroalkanes. The method is highly tolerant of various functional groups and substitution patterns. These functionally dense products serve as orthogonally masked 1,3-diamines, which can be revealed selectively for access to differentially

  铜催化现在可以使硝基链烷烃与α-溴腈高效C-烷基化。使用简单且廉价的催化剂，该方法提供了获得β-氰基硝基链烷的途径。该方法高度耐受各种官能团和取代模式。这些功能密集的产物用作正交掩蔽的1,3-二胺，可以选择性地显示出它们以获取差异取代的二胺。这些产物也可用于形成复杂的氰基烯烃和5-氨基异恶唑。
• An Unprecedented Pseudo-[3+2] Annulation between <i>N</i> -(4-Methoxyphenyl)aldimines and Aqueous Glutaraldehyde: Direct Synthesis of Pyrrole-2,4-dialdehydes
  作者：Panduga Ramaraju、Nisar A. Mir、Deepika Singh、Preetika Sharma、Rajni Kant、Indresh Kumar

  DOI：10.1002/ejoc.201700500

  日期：2017.6.30

  A new method for the direct one-pot synthesis of substituted pyrrole-2,4-dialdehdyes was developed. This overall pseudo-[3+2]-annulation reaction between glutaraldehyde and N-(4-methoxyphenyl)aldimines proceeds through proline-catalyzed direct Mannich reaction/cyclization, followed by 2-iodoxybenzoic acid mediated oxidative rearrangement of the in situ generated intermediate to give pyrrole-2,4-dialdehydes

  提出了一种直接一锅法合成取代吡咯-2,4-二醛的新方法。戊二醛和N-（4-甲氧基苯基）醛亚胺之间的总体假[3 + 2]环化反应是通过脯氨酸催化的直接曼尼希反应/环化进行的，然后由2-碘氧基苯甲酸介导的原位生成的中间体与中间体的氧化重排以高收率（最高80％）得到吡咯-2,4-二醛。
• Direct catalytic synthesis of densely substituted 3-formylpyrroles from imines and 1,4-ketoaldehydes
  作者：Indresh Kumar、Nisar A. Mir、Panduga Ramaraju、Deepika Singh、Vivek K. Gupta、Rajnikant Rajnikant

  DOI：10.1039/c4ra06581f

  日期：——

  An organocatalytic formal [3 + 2] cycloaddition have been developed between 1,4-ketoaldehydes and imines to synthesize densely substituted 3-formylpyrroles in high yields (up to 70%) under mild conditions at room temperature.

  已开发出一种在室温下在温和条件下，通过1,4-酮醛和亚胺之间的有机催化形式[3 + 2]环加成反应，合成高产率（高达70%）的密集取代的3-甲酰吡咯。
• Enantioselective Synthesis of N−N Biaryl Atropisomers through Iridium(I)‐Catalyzed C−H Alkylation with Acrylates
  作者：Si‐Yong Yin、Qiansujia Zhou、Chen‐Xu Liu、Qing Gu、Shu‐Li You

  DOI：10.1002/anie.202305067

  日期：2023.9.11

  A highly efficient iridium-catalyzed asymmetric C−H alkylation reaction is described. A series of structurally diverse indole-pyrrole and pyrrole-pyrrole N−N atropisomers were obtained in good yields (up to 98 %) with excellent enantioselectivity (up to 99 % ee). This reaction features perfect atom economy, wide substrate scope, and multifunctionalized products allowing diverse transformations.

  描述了一种高效的铱催化不对称 CH 烷基化反应。以良好的收率（高达 98%）和优异的对映选择性（高达 99% ee）获得了一系列结构多样的吲哚-吡咯和吡咯-吡咯 N−N 阻转异构体。该反应具有完美的原子经济性、广泛的底物范围以及允许多种转化的多功能化产物。