(cyclohexene-1,2-diyl-bisethynyl)-bisbenzene | 31144-31-7

• 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: (cyclohexene-1,2-diyl-bisethynyl)-bisbenzene
• 英文别名: 1,2-di(2-phenyl-1-ethynyl)-1-cyclohexene；1,2-bis-(phenylethinyl)cyclohexene；1,2-Bis(phenylethynyl)cyclohexene；1,2-bis-phenylethynylcyclohexene；1,2-Bis-(phenylethinyl)-cyclohexen-1；2-[2-(2-Phenylethynyl)cyclohexen-1-yl]ethynylbenzene
• CAS: 31144-31-7
• 化学式: C₂₂H₁₈
• 分子量: 282.385
• InChiKey: FNSQKUHSRIPRPA-UHFFFAOYSA-N

物化性质

• 熔点：
  72 °C
• 沸点：
  419.0±45.0 °C(Predicted)
• 密度：
  1.10±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.6
• 重原子数：
  22
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.18
• 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：

  (cyclohexene-1,2-diyl-bisethynyl)-bisbenzene 在 1,4-环己二烯 作用下， 以 二苯醚 为溶剂， 以80%的产率得到6,7-diphenyl-1,2,3,4-tetrahydronaphthalene
  参考文献：
  名称：

  Polar Effects in the Transition State of the Bergman Cyclization

  摘要：

  从烯二炔 1a-c 的动力学数据得出结论，吸电子取代基通过降低面内 π 轨道的排斥力来降低伯格曼环芳构化中的自由活化能。

  DOI：

  10.1246/cl.1995.953
• 作为产物：
  描述：

  己二酰氯 在 manganese(II) iodide 、 正丁基锂 、 四氯化钛 、 锌 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 反应 2.0h， 生成 (cyclohexene-1,2-diyl-bisethynyl)-bisbenzene
  参考文献：
  名称：

  Synthesis and Protein Degradation Capacity of Photoactivated Enediynes

  摘要：

  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.

  DOI：

  10.1021/jo051403q

文献信息

• Formation of enediynes by reductive coupling followed by alkyne metathesis
  申请人：——

  公开号：US20040215028A1

  公开（公告）日：2004-10-28

  One aspect of the present invention relates to methods of preparing enedialkylidyne complexes, enediynes, and alkyne metathesis catalysts, as well as methods of catalyzing alkyne metathesis reactions. The present invention also relates to methods of activating enedialkylidyne complexes for metathesis. The present invention also relates to enedialkylidyne complexes.

  本发明的一个方面涉及制备烯二烷基炔基化合物、烯二炔和炔基重排催化剂的方法，以及催化炔基重排反应的方法。本发明还涉及激活烯二烷基炔基化合物进行重排反应的方法。本发明还涉及烯二烷基炔基化合物。
• 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.
• Fancy bioisosteres: synthesis and dopaminergic properties of the endiyne FAUC 88 as a novel non-aromatic D3 agonist
  作者：Carola Lenz、Christian Haubmann、Harald Hübner、Frank Boeckler、Peter Gmeiner

  DOI：10.1016/j.bmc.2004.09.044

  日期：2005.1

  Enlargement of the pi-electronic system of the non-aromatic D3 agonist FAUC 73 led to dopaminergic endiynes of type 1 being synthesized via the bromovinyl triflate 7a as a key intermediate when palladium catalyzed coupling reactions were exploited for the introduction of the (aza)alkyne substituents. As the first neuroreceptor active endiyne, FAUC 88 (1c) displayed high and selective dopamine D3 receptor affinity (K-i high = 3.2 nM) and substantial ligand efficacy (72%, EC50 = 2.5 nM). Similarities between molecular electrostatic potentials induced by the catechol subunit of the genuine neurotransmitter and those of its non-aromatic endiyne bioisostere are discussed. (C) 2004 Elsevier Ltd. All rights reserved.
• 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
• Mueller,E. et al., Justus Liebigs Annalen der Chemie, 1971, vol. 750, p. 63 - 75
  作者：Mueller,E. et al.

  DOI：——

  日期：——