dodec-5-yn-2-one | 132716-18-8

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: dodec-5-yn-2-one
• 英文别名: 5-dodecyn-2-one
• CAS: 132716-18-8
• 化学式: C₁₂H₂₀O
• 分子量: 180.29
• InChiKey: NLLNPWHYJAZQIZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  13
• 可旋转键数：
  6
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.75
• 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：

  dodec-5-yn-2-one 在 双(乙腈)氯化钯(II) 水 作用下， 以 乙腈 为溶剂， 反应 1.0h， 以81%的产率得到dodecane-2,5-dione
  参考文献：
  名称：

  Synthesis of substituted furans by palladium-catalyzed cyclization of acetylenic ketones

  摘要：

  Palladium-catalyzed cyclization of beta,gamma-acetylenic ketones gives furans by intramolecular oxypalladation and subsequent protodemetalation. 3-Allylfurans were exclusively obtained by trapping the intermediate 3-furyl-palladium species with allyl halides in the presence of 2,2-dimethyloxirane as a proton scavenger.

  DOI：

  10.1021/jo00020a024
• 作为产物：
  描述：

  Dodec-5-yn-2-ol 在 jones reagent 作用下， 生成 dodec-5-yn-2-one
  参考文献：
  名称：

  Palladium-catalyzed intramolecular addition of amines to acetylenes. Synthesis of cyclic imines

  摘要：

  Intramolecular aminopalladation of alkynylamines gave intermediary alkenylpalladium compounds that hydrolyzed and isomerized to thermodynamically stable cyclic imines. Treatment of 3-alkynylamines with a catalytic amount of PdCl2(MeCN)2 gave exclusively 1-pyrrolines in good yields; 5-alkynylamines afforded 2,3,4,5-tetrahydropyridines selectively. Treatment of 4-alkynylamines with Pd(II) afforded mixtures of both 5- and 6-membered cyclic imines. Applications to the synthesis of some naturally occurring alkaloids are also described.

  DOI：

  10.1021/jo00020a023

文献信息

• Palladium-catalyzed 1,4-addition of terminal alkynes to unsaturated carbonyl compounds promoted by electron-rich ligands
  作者：Lei Zhou、Liang Chen、Rachid Skouta、Huan-feng Jiang、Chao-Jun Li

  DOI：10.1039/b805946m

  日期：——

  The efficient palladium-catalyzed conjugate addition of terminal alkynes to α,β-unsaturated carbonyl compounds has been developed using electron-rich ligands, producing the corresponding γ,δ-alkynyl ketone and γ,δ-alkynyl esters in good yields.

  利用富电子配体，已经开发出了高效的钯催化端炔对α,β-不饱和羰基化合物的共轭加成反应，产率良好地得到了相应的γ,δ-炔基酮和γ,δ-炔基酯。
• New type formation of 1,3-enynes (or internal alkynes) via coupling of organoboranes with alkynylcopper compounds mediated by copper(II)
  作者：Yuzuru Masuda、Kaname Sato

  DOI：10.1039/a800242h

  日期：——

  The copper(II)—mediated coupling reaction of alkenyldialkyl- or trialkyl-boranes with alkynylcopper compounds (generated in situ), in the presence of appropriate solvents and a small amount of water, gives (E)-1,3-enynes (or disubstituted alkynes) with various functional groups in reasonable yields.

  铜(II)介导的烯烃二烷基或三烷基硼酸盐与烷炔铜化合物（原位生成）的偶联反应，在适当溶剂和少量水的存在下，能够以合理的产率生成各种功能团的(E)-1,3-烯炔（或二取代烷炔）。
• Rhodium-catalyzed 1,4-addition of terminal alkynes to vinyl ketones
  作者：Ronald V. Lerum、John D. Chisholm

  DOI：10.1016/j.tetlet.2004.07.036

  日期：2004.8

  useful catalyst system for the 1,4-addition of alkynes to unsubstituted vinyl ketones. Best yields are obtained when the transformation is performed in benzene at reflux with an excess of vinyl ketone. Both aryl and alkyl substituted alkynes participate in the reaction. Primary alcohols and alkyl chlorides are well tolerated under these reaction conditions. The reaction also proceeds in aqueous solvent

  在等摩尔量的三（邻甲氧基苯基）膦存在下，金属络合物Rh（acac）（CO）2为炔烃1,4-加成至未取代的乙烯基酮提供了有用的催化剂体系。当在苯中以过量的乙烯基酮在回流下进行转化时，可获得最佳产率。芳基和烷基取代的炔烃均参与该反应。在这些反应条件下，伯醇和烷基氯具有良好的耐受性。与大多数有机金属加成反应不同，该反应还可以在水性溶剂混合物中进行。
• The first palladium-catalyzed 1,4-addition of terminal alkynes to conjugated enones
  作者：Liang Chen、Chao-Jun Li

  DOI：10.1039/b407936a

  日期：——

  The first palladium-catalyzed 1,4-addition of terminal alkynes to conjugated enones has been developed in water and in acetone, producing the corresponding gamma,delta-alkynyl ketones in high yields.

  在水和丙酮中​​已经开发出钯在末端炔烃与共轭烯酮的第一种钯催化的1,4-加成反应，可高产率地生产相应的γ-δ-炔基酮。
• Synthesis and Antibacterial Evaluation of a New Series of N-Alkyl-2-alkynyl/(E)-alkenyl-4-(1H)-quinolones
  作者：Abraham Wube、Juan-David Guzman、Antje Hüfner、Christina Hochfellner、Martina Blunder、Rudolf Bauer、Simon Gibbons、Sanjib Bhakta、Franz Bucar

  DOI：10.3390/molecules17078217

  日期：——

  To gain further insight into the structural requirements of the aliphatic group at position 2 for their antimycobacterial activity, some N-alkyl-4-(1H)-quinolones bearing position 2 alkynyls with various chain length and triple bond positions were prepared and tested for in vitro antibacterial activity against rapidly-growing strains of mycobacteria, the vaccine strain Mycobacterium bovis BCG, and

  为了进一步了解 2 位脂肪族基团的抗分枝杆菌活性的结构要求，一些 N-烷基-4-(1H)-喹诺酮类在 2 位具有不同链长和三键位置的炔基被制备和测试。对快速生长的分枝杆菌菌株、疫苗菌株牛分枝杆菌 BCG 和耐甲氧西林金黄色葡萄球菌菌株 EMRSA-15 和 -16 的体外抗菌活性。还评估了化合物对结核分枝杆菌的 ATP 依赖性 MurE 连接酶的抑制作用。对偶发分枝杆菌和耻垢分枝杆菌的最低 MIC 值为 0.5 mg/L (1.2–1.5 µM)。这些化合物在 100 µM 浓度下对人肺成纤维细胞系 MRC-5 没有或只有微弱的毒性。喹诺酮衍生物对流行的 MRSA 菌株（EMRSA-15 和 -16）表现出显着的活性，MIC 值为 2–128 mg/L（5.3–364.7 µM），对牛分枝杆菌 BCG 的 MIC 值为 25 mg/L (66.0–77.4 µM)。此外，这些化合物抑制结核分枝杆菌的