1,5-diphenylpent-1-en-4-yne | 24765-03-5

• 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: 1,5-diphenylpent-1-en-4-yne
• 英文别名: 1,5-Diphenyl-pent-4-en-1-in；5-Phenylpent-1-en-4-ynylbenzene；5-phenylpent-1-en-4-ynylbenzene
• CAS: 24765-03-5
• 化学式: C₁₇H₁₄
• 分子量: 218.298
• InChiKey: VRWZXXZADIOAKU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.9
• 重原子数：
  17
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.06
• 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：

  1,5-diphenylpent-1-en-4-yne 在 dicobalt octacarbonyl 、 cerric ammonium sulphate 、 溴 作用下， 生成 4,5-dibromo-1,5-diphenylpent-1-yne
  参考文献：
  名称：

  Drewes, Siegfried E.; Slater-Kinghorn, Barbara J., Synthetic Communications, 1986, vol. 16, # 5, p. 603 - 610

  摘要：

  DOI：
• 作为产物：
  描述：

  1,5-diphenyl-4-penten-1-yn-3-ol 在 三乙基硅烷 、 [(η⁵-C5Me5)RuCl(μ₂-SMe)2Ru(η⁵-C5Me5)(OH2)]OTf 作用下， 以 1,2-二氯乙烷 为溶剂， 反应 1.0h， 以51%的产率得到1,5-diphenylpent-1-en-4-yne
  参考文献：
  名称：

  钌催化的炔丙醇与硅烷的炔丙基还原。

  摘要：

  DOI：

  10.1002/anie.200601181

文献信息

• Copper catalyzed regioselective coupling of allylic halides and alkynes promoted by weak inorganic bases
  作者：Lothar W. Bieber、Margarete F. da Silva

  DOI：10.1016/j.tetlet.2007.08.010

  日期：2007.10

  Allylic halides and terminal alkynes couple under CuI catalysis in DMSO or DMF solution. In most cases, sodium carbonate or bicarbonate is sufficient to promote the reaction; less reactive alkynes require catalytic amounts of DBU. Bifunctional alkynes and halides can be reacted selectively according to the stoichiometry used. Trimethylsilyl, hydroxyl, ester and halide groups are tolerated in the alkyne

  烯丙基卤化物和末端炔烃在CuI催化下在DMSO或DMF溶液中偶联。在大多数情况下，碳酸钠或碳酸氢钠足以促进反应。反应性较低的炔烃需要催化量的DBU。双官能炔烃和卤化物可以根据所用的化学计量选择性地反应。炔烃中可容忍三甲基甲硅烷基，羟基，酯和卤化物基团。大多数卤化物反应时不进行烯丙基重排。该方法适合于官能化的炔烃的合成。
• Recyclable heterogeneous metal foil-catalyzed cyclopropenation of alkynes and diazoacetates under solvent-free mechanochemical reaction conditions
  作者：Longrui Chen、Devonna Leslie、Michael G. Coleman、James Mack

  DOI：10.1039/c8sc00443a

  日期：——

  cyclopropenation of terminal and internal alkynes under mechanochemical reaction conditions. This methodology enables the functionalization of a wide range of terminal or internal alkynes under ambient, aerobic, and solvent-free conditions. Finally, we have demonstrated a unique and versatile one-pot domino Sonogashira-cyclopropenation mechanochemical reaction for the formation of complex cyclopropenes.

  发现银和铜箔是在机械化学反应条件下用于末端炔烃和内部炔烃环丙烷化的有效，通用和选择性的非均相催化剂。这种方法可以在环境，好氧和无溶剂条件下使各种末端或内部炔烃官能化。最后，我们展示了一种独特而通用的一锅多米诺多米诺Sonogashira-环丙烷化机械化学反应，用于形成复杂的环丙烯。
• Decarboxylative/Sonogashira-type cross-coupling using PdCl₂(Cy*Phine)₂
  作者：Yong Yang、Yee Hwee Lim、Edward G. Robins、Charles W. Johannes

  DOI：10.1039/c6ra12916a

  日期：——

  Expedient protocol to access a wide range of internal alkynes and symmetrical di(heteroaryl)alkynesviatandem decarboxylative–Sonogashira cross-coupling.

  通过串联脱羧化-Sonogashira交叉偶联方法访问广泛的内部炔烃和对称的双(杂环烷基)炔烃。
• One-Pot Synthesis of Decahydropyrene via Tandem C–H Activation/Intramolecular Diels–Alder/1,3-Dipolar Cycloaddition
  作者：Hui Lin、Lin Dong

  DOI：10.1021/acs.orglett.6b02768

  日期：2016.11.4

  A novel decahydropyrene synthesis has been successfully developed involving a tandem rhodium-catalyzed C–H activation/intramolecular Diels–Alder reaction/1,3-dipolar cycloaddition cascade process by using diazole as a traceless directing group. The advantage of this one-pot strategy is a quite simple, efficient, highly stereoselective, and unique product structure.

  已成功开发了一种新颖的十氢involving合成方法，该方法以重氮为直接基，通过串联铑催化的C–H活化/分子间Diels–Alder反应/ 1,3-偶极环加成级联过程。这种一站式策略的优势是非常简单，高效，高度立体选择性和独特的产品结构。
• Iridium-Catalyzed Enantioselective Allylic Alkynylation
  作者：James Y. Hamilton、David Sarlah、Erick M. Carreira

  DOI：10.1002/anie.201302731

  日期：2013.7.15

  No leaving group needed: With an Ir(P,olefin) complex as catalyst, the direct enantioselective allylic alkynylation of secondary allylic alcohols with potassium alkynyltrifluoroborates as alkynylating reagents has been achieved. High levels of enantioselectivity and high yields were achieved with this operationally easy and robust protocol, the use of which was demonstrated in the synthesis of GPR40 receptor agonist AMG 837. cod = 1,5-cyclooctadiene.