1-(but-1-yn-1-yl)cyclohex-1-ene | 5680-44-4

• 分子结构分类: 有机化合物 - 碳氢化合物 - 不饱和烃
• 英文名称: 1-(but-1-yn-1-yl)cyclohex-1-ene
• 英文别名: 1-(but-1-yn-1-yl)cyclohexene；1--but-1-in；Cyclohexen-(1)-yl-(1)-butin-(1)；1-(Cyclohex-1-enyl)-but-1-in；1-But-1-ynylcyclohexene
• CAS: 5680-44-4
• 化学式: C₁₀H₁₄
• 分子量: 134.221
• InChiKey: PJVXQLRWOFXZTH-UHFFFAOYSA-N

物化性质

• 沸点：
  204.8±10.0 °C(Predicted)
• 密度：
  0.88±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  10
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.6
• 拓扑面积：
  0
• 氢给体数：
  0
• 氢受体数：
  0

反应信息

• 作为反应物：
  描述：

  1-(but-1-yn-1-yl)cyclohex-1-ene 在 Lindlar's catalyst 喹啉 、 氢气 、 碘 作用下， 以 Petroleum ether 为溶剂， 生成 1-but-1-en-t-yl-cyclohexene
  参考文献：
  名称：

  Catalyst Selectivity in Semihydrogenation of Some Conjugated Acetylenes¹

  摘要：

  DOI：

  10.1021/jo01022a535
• 作为产物：
  描述：

  环己醇,1-(1-丁炔基)- 在 吡啶 、 甲基磺酰氯 作用下， 反应 60.0h， 以74%的产率得到1-(but-1-yn-1-yl)cyclohex-1-ene
  参考文献：
  名称：

  Synthesis of Isoquinolines and Pyridines by the Palladium-Catalyzed Iminoannulation of Internal Alkynes

  摘要：

  A wide variety of substituted isoquinoline, tetrahydroisoquinoline, 5,6-dihydrobenz[f]isoquinoline, pyrindine, and pyridine heterocycles have been prepared in good to excellent yields via annulation of internal acetylenes with the tert-butylimines of o-iodobenzaldehydes and 3-halo-2-alkenals in the presence of a palladium catalyst. The best results are obtained by employing 5 mol % of Pd(OAc)(2), an excess of the alkyne, 1 equiv of Na2CO3 as a base, and 10 mol % of PPh3 in DMF as the solvent. This annulation methodology is particularly effective for aryl- or alkenyl-substituted alkynes. When electron-rich imines are employed, this chemistry can be extended to alkyl-substituted alkynes. Trimethylsilyl-substituted alkynes also undergo this annulation process to afford monosubstituted heterocyclic products absent the silyl group.

  DOI：

  10.1021/jo0105540

文献信息

• Substituted quinolines as noncovalent proteasome inhibitors
  作者：Tanner J. McDaniel、Theresa A. Lansdell、Amila A. Dissanayake、Lauren M. Azevedo、Jacob Claes、Aaron L. Odom、Jetze J. Tepe

  DOI：10.1016/j.bmc.2016.04.005

  日期：2016.6

  Screening of a library of diverse heterocyclic scaffolds identified substituted quinolines as inhibitors of the human proteasome. The heterocyclic library was prepared via a novel titanium-catalyzed multicomponent coupling reaction, which rendered a diverse set of isoxazoles, pyrimidines, pyrroles, pyrazoles and quinolines. SAR of the parent lead compound indicated that hydrophobic residues on the

  对不同杂环支架文库的筛选鉴定出取代的喹啉作为人类蛋白酶体的抑制剂。该杂环库是通过一种新型钛催化多组分偶联反应制备的，该反应产生了多种异恶唑、嘧啶、吡咯、吡唑和喹啉。母体先导化合物的 SAR 表明苯并部分上的疏水残基显着提高了效力。先导化合物25抑制蛋白酶体的胰凝乳蛋白酶样蛋白水解活性 (IC 50 5.4 μM)，代表一类新的非肽、非共价蛋白酶体抑制剂。
• Metal free carboamination of internal alkynes – an easy access to polysubstituted quinolines
  作者：T. Stopka、M. Niggemann

  DOI：10.1039/c5cc10460b

  日期：——

  A transition metal free carboamination of unactivated alkynes towards highly substituted quinolines was realized in the presence of a synergistic Bronsted acid based catalyst system. The mechanism was confirmed to...

  在协同的布朗斯台德酸基催化剂体系的存在下，实现了未活化的炔烃向高度取代的喹啉的无过渡金属无碳氨化反应。该机制被确认为...
• Silver Triflate-Catalyzed Cyclopropenation of Internal Alkynes with Donor-/Acceptor-Substituted Diazo Compounds
  作者：John F. Briones、Huw M. L. Davies

  DOI：10.1021/ol201503j

  日期：2011.8.5

  Silver triflate was found to be an efficient catalyst for the cyclopropenation of internal alkynes using donor-/acceptor-substituted diazo compounds as carbenoid precursors. Highly substituted cyclopropenes, which cannot be synthesized directly via rhodium(II)-catalyzed carbenoid chemistry, can now be readily accessed.
• Gold(I)-Catalyzed Asymmetric Cyclopropenation of Internal Alkynes
  作者：John F. Briones、Huw M. L. Davies

  DOI：10.1021/ja304506g

  日期：2012.7.25

  Highly enantioselective cyclopropenation of internal alkynes with aryldiazoacetates was achieved using the binuclear gold catalyst (S)-xylylBINAP(AuCl)(2), activated by silver hexafluoroantimonate.
• DELBECQ F.; BADOUY R.; GORE J., NOUV. J. CHIM., 1979, 3, NO 5, 321-327
  作者：DELBECQ F.、 BADOUY R.、 GORE J.

  DOI：——

  日期：——