4-pent-1-ynyl-benzaldehyde | 1426054-62-7

• 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: 4-pent-1-ynyl-benzaldehyde
• 英文别名: 4-Pent-1-ynylbenzaldehyde
• CAS: 1426054-62-7
• 化学式: C₁₂H₁₂O
• 分子量: 172.227
• InChiKey: JRQRDIPLTBRIFR-UHFFFAOYSA-N

物化性质

• 沸点：
  289.0±23.0 °C(Predicted)
• 密度：
  1.02±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  13
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  17.1
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  4-pent-1-ynyl-benzaldehyde 在 palladium 10% on activated carbon 、 氢气 作用下， 以 乙酸乙酯 为溶剂， 生成 4-正戊基苯甲醛
  参考文献：
  名称：

  Antimycobacterial activity evaluation, time-kill kinetic and 3D-QSAR study of C-(3-aminomethyl-cyclohexyl)-methylamine derivatives

  摘要：

  A series of C-(3-aminomethyl-cyclohexyl)-methylamine derivatives were synthesized and evaluated for their antitubercular activity. Some of the compounds exhibited potent activity against Mycobacterium tuberculosis H37Rv. One of the compound having t-butyl at para position of the benzene ring showed excellent activity even better than the standard drug ethambutol with MIC value 1.1 +/- 0.2 mu M. The time-kill kinetics study of two most active compounds showed rapid killing of the M. tuberculosis within 4 days. Additionally atom-based quantitative structure-activity relationship (QSAR) model was developed that gave a statistically satisfying result (R-2) = 0.92, Q(2) = 0.75, Pearson-R = 0.96 and effectively predicts the anti-tuberculosis activity of training and test set compounds. (c) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2012.12.083
• 作为产物：
  描述：

  1-戊炔 、 对溴苯甲醛 在 copper(l) iodide 、 bis(triphenylphosphine)palladium(II) dichloride 、 三乙胺 作用下， 以 四氢呋喃 为溶剂， 反应 12.0h， 生成 4-pent-1-ynyl-benzaldehyde
  参考文献：
  名称：

  Antimycobacterial activity evaluation, time-kill kinetic and 3D-QSAR study of C-(3-aminomethyl-cyclohexyl)-methylamine derivatives

  摘要：

  A series of C-(3-aminomethyl-cyclohexyl)-methylamine derivatives were synthesized and evaluated for their antitubercular activity. Some of the compounds exhibited potent activity against Mycobacterium tuberculosis H37Rv. One of the compound having t-butyl at para position of the benzene ring showed excellent activity even better than the standard drug ethambutol with MIC value 1.1 +/- 0.2 mu M. The time-kill kinetics study of two most active compounds showed rapid killing of the M. tuberculosis within 4 days. Additionally atom-based quantitative structure-activity relationship (QSAR) model was developed that gave a statistically satisfying result (R-2) = 0.92, Q(2) = 0.75, Pearson-R = 0.96 and effectively predicts the anti-tuberculosis activity of training and test set compounds. (c) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2012.12.083

文献信息

• [EN] SUBSTITUTED AMINO-AZA-CYCLOHEXANES<br/>[FR] AMINO-AZA-CYCLOHEXANES SUBSTITUES
  申请人：ACTELION PHARMACEUTICALS LTD

  公开号：WO2005019176A1

  公开（公告）日：2005-03-03

  The invention relates to novel amino-aza-cyclohexane derivatives and related compounds and their use as active ingredients in the preparation of pharmaceutical compositions. The invention also concerns related aspects including processes for the preparation of the compounds, pharmaceutical compositions containing one or more of those compounds and especially their use as inhibitors of plasmepsin II.

  本发明涉及新型氨基-氮杂环己烷衍生物及相关化合物，并将其用作制备制药组合物的活性成分。本发明还涉及相关方面，包括化合物的制备过程，含有其中一种或多种化合物的制药组合物，特别是它们作为血浆蛋白酶II的抑制剂的用途。
• Controlling Selectivity in Shuttle Hetero‐difunctionalization Reactions: Electrochemical Transfer Halo‐thiolation of Alkynes
  作者：Xichang Dong、Martin Klein、Siegfried R. Waldvogel、Bill Morandi

  DOI：10.1002/anie.202213630

  日期：2023.1.9

  Shuttle catalysis is emerging as a potent strategy to unleash unprecedented synthetic flexibility in organic synthesis. Herein, we disclose a rare example of shuttle hetero-difunctionalization to transfer two distinct functional groups between β-halosulfides and alkynes with excellent chemo-, regio-, and stereoselectivity via a paired electrolysis process. This unfolds new opportunities for selective

  穿梭催化正在成为释放有机合成中前所未有的合成灵活性的有效策略。在此，我们公开了一个罕见的穿梭异双官能化实例，通过配对电解过程在 β-卤硫化物和炔烃之间转移两个不同的官能团，具有出色的化学选择性、区域选择性和立体选择性。这为选择性穿梭双功能化反应提供了新的机会。
• Nickel‐Catalyzed Sonogashira Couplings: Extending the Reaction Scope to Aryl Bromides and Chlorides
  作者：Elena Braconi、Edouard Godineau、Tomas Smejkal、Simon Jäckh

  DOI：10.1002/adsc.202301423

  日期：2024.4.9

  documented, the coupling of more challenging yet cost-effective aryl bromides and chlorides lags significantly behind. Herein, we present a method for the nickel-catalyzed Sonogashira coupling of aryl bromides and chlorides, whose discovery was accelerated thanks to high-throughput experimentation. Fine-tuning of the bipyridine ligand was essential to activate chemoselectively C(sp2)–Br or C(sp2)–Cl bonds

  炔烃基序存在于几种天然存在的环分子和特种化学品中。 Sonogashira反应被认为是合成取代炔烃最常用的方法之一。虽然传统上使用钯催化剂，但最近的努力致力于开发基于地球丰富的金属（例如镍）的替代品。然而，镍催化的 Sonogashira 偶联仍然存在重要的底物限制。虽然反应性更强的芳基碘化物已得到充分证明，但更具挑战性但更具成本效益的芳基溴化物和氯化物的偶联却明显落后。在此，我们提出了一种镍催化的芳基溴化物和氯化物的 Sonogashira 偶联方法，由于高通量实验加速了该方法的发现。联吡啶配体的微调对于化学选择性激活 C(sp2)–Br 或 C(sp2)–Cl 键。只需一步即可获得多种功能多样的炔烃，包括活性成分及其中间体的示例，收率高达 98%。该方法有望被学术界和工业界广泛采用，标志着贱金属催化领域向前迈进了一步。
• Antimycobacterial activity evaluation, time-kill kinetic and 3D-QSAR study of C-(3-aminomethyl-cyclohexyl)-methylamine derivatives
  作者：Deepak Kumar、K. Kranthi Raj、MaiAnn Bailey、Torey Alling、Tanya Parish、Diwan S. Rawat

  DOI：10.1016/j.bmcl.2012.12.083

  日期：2013.3

  A series of C-(3-aminomethyl-cyclohexyl)-methylamine derivatives were synthesized and evaluated for their antitubercular activity. Some of the compounds exhibited potent activity against Mycobacterium tuberculosis H37Rv. One of the compound having t-butyl at para position of the benzene ring showed excellent activity even better than the standard drug ethambutol with MIC value 1.1 +/- 0.2 mu M. The time-kill kinetics study of two most active compounds showed rapid killing of the M. tuberculosis within 4 days. Additionally atom-based quantitative structure-activity relationship (QSAR) model was developed that gave a statistically satisfying result (R-2) = 0.92, Q(2) = 0.75, Pearson-R = 0.96 and effectively predicts the anti-tuberculosis activity of training and test set compounds. (c) 2012 Elsevier Ltd. All rights reserved.