1-(1-ethynyl)-2-(2-phenyl-1-ethynyl)-1-cyclohexene | 303142-40-7

• 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: 1-(1-ethynyl)-2-(2-phenyl-1-ethynyl)-1-cyclohexene
• 英文别名: (2-ethynyl-cyclohex-1-enylethynyl)benzene；1-ethynyl-2-(phenylethynyl)-1-cyclohexene；[(2-Ethynylcyclohex-1-en-1-yl)ethynyl]benzene；2-(2-ethynylcyclohexen-1-yl)ethynylbenzene
• CAS: 303142-40-7
• 化学式: C₁₆H₁₄
• 分子量: 206.287
• InChiKey: RFUJPJYENUHANK-UHFFFAOYSA-N

物化性质

• 沸点：
  299.1±40.0 °C(Predicted)
• 密度：
  1.04±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  16
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.25
• 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-(1-ethynyl)-2-(2-phenyl-1-ethynyl)-1-cyclohexene 在 对甲苯磺酸 作用下， 以 苯 为溶剂， 反应 30.0h， 以75%的产率得到3-(1-环己烯-1-基)-2-丙炔-1-醇
  参考文献：
  名称：

  Gold-Catalyzed Intramolecular [3 + 2]-Cycloaddition of Arenyne-Yne Functionalities

  摘要：

  We report a new efficient intramolecular [3 + 2]-cycloaddition of unactivated arenyne (or enyne)-yne functionalities, catalyzed mainly by the AuPPh3SbF6 complex (2 mol %) under ambient conditions. The value of this cyclization is reflected by its applicability to a wide range of diyne substrates bearing various functional groups.

  DOI：

  10.1021/ja0643826
• 作为产物：
  描述：

  2-溴-1-环己烯-1-甲醛 在 copper(l) iodide 、 四(三苯基膦)钯 三乙胺 、 三苯基膦 、 lithium diisopropyl amide 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 16.0h， 生成 1-(1-ethynyl)-2-(2-phenyl-1-ethynyl)-1-cyclohexene
  参考文献：
  名称：

  Gold-Catalyzed Intramolecular [3 + 2]-Cycloaddition of Arenyne-Yne Functionalities

  摘要：

  We report a new efficient intramolecular [3 + 2]-cycloaddition of unactivated arenyne (or enyne)-yne functionalities, catalyzed mainly by the AuPPh3SbF6 complex (2 mol %) under ambient conditions. The value of this cyclization is reflected by its applicability to a wide range of diyne substrates bearing various functional groups.

  DOI：

  10.1021/ja0643826

文献信息

• Novel Chemistry of α-Tosyloxy Ketones:  Applications to the Solution- and Solid-Phase Synthesis of Privileged Heterocycle and Enediyne Libraries
  作者：K. C. Nicolaou、T. Montagnon、T. Ulven、P. S. Baran、Y.-L. Zhong、F. Sarabia

  DOI：10.1021/ja012146j

  日期：2002.5.1

  preparation and elaboration of alpha-tosyloxy ketones in solution- and on solid-phase are described. Both olefins and ketones serve as precursors to these relatively stable chemical entities: olefins via a novel one-pot epoxidation, arylsulfonic acid displacement, and oxidation sequence, and ketones by direct exposure to arylsulfonic acids in the presence of diacetoxy iodobenzene. Reaction of these substrates

  描述了在溶液和固相中制备和加工 α-甲苯磺酰氧基酮的新合成技术。烯烃和酮都是这些相对稳定的化学实体的前体：烯烃通过新型的一锅环氧化、芳基磺酸置换和氧化序列，以及酮通过在二乙酰氧基碘苯存在下直接暴露于芳基磺酸。这些底物与 O-、S-或 N-中心亲核试剂的反应导致亲核试剂的掺入并伴随磺酸盐的排出，而暴露于双功能亲核试剂提供环状杂环系统。此外，还探讨了以碳为中心的亲核试剂与 α-甲苯磺酰氧基酮的反应。所有这些亲核试剂的整理数据为以下提议提供了令人信服的证据，即当 α-甲苯磺酰氧基酮被“硬”亲核试剂与“软”亲核试剂结合时，会遵循不同的反应途径。此处展示的化学的可及性和位点选择性为该部分在固相库构建中的扩展用途提供了希望，特别是在有机合成领域，一般而言。
• Synthesis and Protein Degradation Capacity of Photoactivated Enediynes
  作者：Farid S. Fouad、Justin M. Wright、Gary Plourde II,、Ajay D. Purohit、Justin K. Wyatt、Ahmed El-Shafey、George Hynd、Curtis F. Crasto、Yiqing Lin、Graham B. Jones

  DOI：10.1021/jo051403q

  日期：2005.11.1

  The viability of proteins as targets of thermally and photoactivated enediynes has been confirmed at the molecular level. Model studies using a labeled substrate confirmed the efficacy of atom transfer from diyl radicals produced from enediynes to form captodatively stabilized carbon centered aminoacyl radicals, which then undergo either fragmentation or dimerization. To exploit this finding, a family of enediynes was developed using an intramolecular coupling strategy. Derivatives were prepared and used to target specific proteins, showing good correlation between affinity and photoinduced protein degrading activity. The findings have potential applications in the design of artificial chemical proteases and add to our understanding of the mechanism of action of the clinically important enediyne antitumor antibiotics.
• Synthesis and Photochemical Activity of Designed Enediynes
  作者：Graham B. Jones、Justin M. Wright、Gary Plourde、Ajay D. Purohit、Justin K. Wyatt、George Hynd、Farid Fouad

  DOI：10.1021/ja000766z

  日期：2000.10.1
• Protein degradation with photoactivated enediyne-amino acid conjugates
  作者：Gary Plourde, II、Ahmed El-Shafey、Farid S. Fouad、Ajay S. Purohit、Graham B. Jones

  DOI：10.1016/s0960-894x(02)00618-2

  日期：2002.10

  A series of photoactivated enediynes was prepared, and successfully employed for the selective degradation of target proteins.
• Gold-Catalyzed Intramolecular [3 + 2]-Cycloaddition of Arenyne-Yne Functionalities
  作者：Jian-Jou Lian、Po-Chiang Chen、Yau-Ping Lin、Hao-Chun Ting、Rai-Shung Liu

  DOI：10.1021/ja0643826

  日期：2006.9.1

  We report a new efficient intramolecular [3 + 2]-cycloaddition of unactivated arenyne (or enyne)-yne functionalities, catalyzed mainly by the AuPPh3SbF6 complex (2 mol %) under ambient conditions. The value of this cyclization is reflected by its applicability to a wide range of diyne substrates bearing various functional groups.