2-(pent-1-yn-1-yl)-5-(trifluoromethyl)benzaldehyde | 743468-26-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 2-(pent-1-yn-1-yl)-5-(trifluoromethyl)benzaldehyde
• 英文别名: 2-Pent-1-ynyl-5-trifluoromethyl-benzaldehyde；2-Pent-1-ynyl-5-(trifluoromethyl)benzaldehyde
• CAS: 743468-26-0
• 化学式: C₁₃H₁₁F₃O
• 分子量: 240.225
• InChiKey: PSCGJRZEDFJWFO-UHFFFAOYSA-N

物化性质

• 沸点：
  290.3±40.0 °C(Predicted)
• 密度：
  1.19±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4
• 重原子数：
  17
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  17.1
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2-(pent-1-yn-1-yl)-5-(trifluoromethyl)benzaldehyde 在 silver trifluoromethanesulfonate 作用下， 以 乙醇 、 乙腈 为溶剂， 反应 20.0h， 生成
  参考文献：
  名称：

  Silver(I)-Catalyzed Addition-Cyclization of Alkyne-Functionalized Azomethines

  摘要：

  AgOTf can catalyze an addition-cyclization tandem between alkyne-azomethine and a nucleophile such as ketone, nitroalkane, water, and terminal alkyne to give a polycyclic amide via six-exo-trig selectivity.

  DOI：

  10.1021/ol4000108
• 作为产物：
  描述：

  1-戊炔 、 3-氟-5-甲氧基苯甲醛 生成 2-(pent-1-yn-1-yl)-5-(trifluoromethyl)benzaldehyde
  参考文献：
  名称：

  PtBr₂-Catalyzed Consecutive Enyne Metathesis−Aromatization of 1-(1-Methoxy-but-3-enyl)-2-(1-alkynyl)benzenes:  Dual Role of the Pt Catalyst

  摘要：

  1,7-Enynes 1, connected through an aromatic ring and bearing a leaving methoxy group at the 4-position, underwent the PtBr2-catalyzed enyne metathesis followed by aromatization in one pot to afford vinyl naphthalenes 3 in good to acceptable yields. The cyclobutene intermediate 11a and another intermediate 2a were isolated, indicating that PtBr2 acts as a dual role catalyst: (1) as a transition metal catalyst, it induces the eryne metathesis to produce 11a starting from 1a, and (2) as a Lewis acid catalyst, it facilitates elimination of MeOH from 2a to give the aromatized product 3a.

  DOI：

  10.1021/jo048273q

文献信息

• Synthesis of Cyclic Alkenyl Ethers via Intramolecular Cyclization of <i>O</i>-Alkynylbenzaldehydes. Importance of Combination between CuI Catalyst and DMF
  作者：Nitin T. Patil、Yoshinori Yamamoto

  DOI：10.1021/jo049416b

  日期：2004.7.1

  remarkably general method for the synthesis of cyclic alkenyl ethers via the Cu(I)-catalyzed intramolecular cyclization of O-alkynylbenzaldehydes has been developed. The survey of metal catalysts and solvents revealed that the combination of copper(I) iodide and DMF was the catalytic system of choice. The reaction most probably proceeds via the nucleophilic addition of alcohols 2 to O-alkynylbenzaldehydes

  已经开发了一种通过Cu（I）催化的O-炔基苯甲醛的分子内环化反应合成环状烯基醚的有效且非常通用的方法。对金属催化剂和溶剂的调查显示，碘化铜（I）和DMF的组合是选择的催化体系。该反应很可能是通过将醇2亲核加成到O-炔基苯甲醛1上来生成相应的半缩醛，随后半缩醛氧对铜配位炔烃的亲核攻击将得到环状产物3。在所有情况下，反应均以区域特异性方式进行，通过6- endo - dig环化反应生成六元内环产物。
• Synthesis of Isoquinolines and Related Heterocycles under Visible-Light Conditions
  作者：Yurong Yuan、Clara Faure、Doriane Menigaux、Mathieu Berthelot、Philippe Belmont、Etienne Brachet

  DOI：10.1021/acs.joc.3c01782

  日期：2023.11.17

  compounds cannot be synthesized due to structural sensitivity. In this context, a seamless reaction pathway toward 6-membered ring nitrogen-containing heterocycles is presented here, offering access to isoquinoline derivatives and related heterocycles.

  可见光催化现在被广泛认为是有效构建各种类型框架的有效方法，特别是高产率的生物活性化合物。然而，这些方法仍然迫切需要进一步发展，因为由于结构敏感性而无法合成某些精致的化合物。在此背景下，本文提出了通往六元环含氮杂环的无缝反应途径，提供了获得异喹啉衍生物和相关杂环的途径。
• Harnessing the Potential of Electron Donor–Acceptor Complexes and N-Centered Radicals: Expanding the Frontiers of Isoquinoline Derivative Synthesis
  作者：Yurong Yuan、Clara Faure、Mathieu Berthelot、Philippe Belmont、Etienne Brachet

  DOI：10.1021/acs.joc.4c00086

  日期：2024.3.1

  alkaloids’ family. In our study, we propose a new method to synthesize the isoquinoline core using an electron donor–acceptor (EDA) complex strategy. Our mechanistic investigations have confirmed that our synthesis process operates through an EDA mechanism, which is not extensively discussed in the literature, particularly regarding its applications on alkynyl substrates. This EDA strategy has proven to be a

  合成含氮杂环支架的研究很重要，因为这些结构在自然界中常见，例如在生物碱家族中。在我们的研究中，我们提出了一种使用电子供体-受体（EDA）复合策略合成异喹啉核心的新方法。我们的机理研究证实，我们的合成过程通过 EDA 机制进行，该机制在文献中没有广泛讨论，特别是在其在炔基底物上的应用方面。这种 EDA 策略已被证明是一种无需金属催化剂即可生产异喹啉支架及其衍生物的简单直接的方法。