pent-3-en-1-yn-3-ylbenzene

• 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: pent-3-en-1-yn-3-ylbenzene
• 英文别名: 3-phenyl-pent-2ξ-en-4-yne；3-Phenyl-pent-2ξ-en-4-in
• 化学式: C₁₁H₁₀
• 分子量: 142.2
• InChiKey: XLOOREWHRGQCNP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.72
• 重原子数：
  11.0
• 可旋转键数：
  1.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.09
• 拓扑面积：
  0.0
• 氢给体数：
  0.0
• 氢受体数：
  0.0

反应信息

• 作为反应物：
  描述：

  苯硅烷 、 pent-3-en-1-yn-3-ylbenzene 在 C₄₀H₄₈Cl₂FeN₂ 、 乙基溴化镁 作用下， 以 2-甲基四氢呋喃 、 四氢呋喃 为溶剂， 以73 %的产率得到
  参考文献：
  名称：

  Iron‐Catalyzed Allylic C(sp³)−H Silylation: Spin‐Crossover‐Efficiency‐Determined Chemoselectivity

  摘要：

  The nuanced role of spin effects remains a critical gap in designing proficient open‐shell catalysts. This study elucidates an iron‐catalyzed allylic C(sp³)−H silylation/alkyne hydrosilylation reaction, in which the spin state of the open‐shell iron catalyst dictates the reaction kinetics and pathway. Specifically, spin crossover led to alkyne hydrosilylation, whereas spin conservation resulted in a novel allylic C(sp³)−H silylation reaction. This chemoselectivity, governed by the spin‐crossover efficiency, reveals an unexpected dimension in spin effects and a first in the realm of transition‐metal‐catalyzed in situ silylation of allylic C(sp³)−H bonds, which had been previously inhibited by the heightened reactivity of alkenes in hydrosilylation reactions. Furthermore, this spin crossover can either accelerate or hinder the reaction at different stages within a single catalytic reaction, a phenomenon scarcely documented. Moreover, we identify a substrate‐assisted C−H activation mechanism, a departure from known ligand‐assisted processes, offering a fresh perspective on C−H activation strategies.

  DOI：

  10.1002/anie.202402044
• 作为产物：
  描述：

  3-phenyl-1-pentyn-3-ol 在 吡啶 、 三氯氧磷 作用下， 生成 pent-3-en-1-yn-3-ylbenzene
  参考文献：
  名称：

  Nasarow; Mistrjukow, Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya, 1958, p. 335,336; engl. Ausg. S. 315, 316

  摘要：

  DOI：

文献信息

• Tandem One-Pot Synthesis of Polysubstituted Pyridines Using the Blaise Reaction Intermediate and 1,3-Enynes
  作者：Yu Sung Chun、Jun Hee Lee、Ju Hyun Kim、Young Ok Ko、Sang-gi Lee

  DOI：10.1021/ol202691b

  日期：2011.12.16

  method for the construction of a pyridine moiety with selective control of substitution patterns has been developed through the sequential reactions of nitrile with a Reformatsky reagent and 1,3-enyne involving regio- and chemoselective addition of the Blaise reaction intermediate to 1,3-enyne, followed by isomerization, cyclization, and an aromatization cascade.

  通过腈与Reformatsky试剂和1,3-烯炔的顺序反应（涉及将Blaise反应中间体与Blaise的区域和化学选择性加成），开发了一种具有选择性控制取代模式的吡啶结构的串联一锅法。 1,3-烯炔，然后进行异构化，环化和芳构化级联。
• Allenyl ester precursors for 1H-inden-1-ol carboxylates: comparisons with their propargylic equivalents having terminal alkyne functions
  作者：Martta Asikainen、Simon Woodward

  DOI：10.1016/j.tet.2012.04.086

  日期：2012.7

  and their isomeric equivalents the terminal propargylic carboxylates, ArC(R1)(O2CR2)CCH, in gold-catalyzed carbocyclization to indenes provides information on 1,3 and 1,2-carboxylate shifts associated with their interconversion. Allenyl carboxylates transform specifically to 1H-inden-1-yl carboxylates in high yields, under AuI-catalysis. Their equivalent propargylic carboxylates give complex mixtures

  在金催化的碳环化反应中烯丙基羧酸盐Ar（R 1）CCCH（O 2 CR 2）的反应性及其端基炔丙基羧酸盐ArC（R 1）（O 2 CR 2）CCH的异构体等价物提供了有关与它们的相互转化有关的1，3和1，2-羧酸盐移位。在Au I-催化下，烯丙基羧酸盐可高产率地特异性转化为1 H-茚-1-基羧酸盐。它们的当量炔丙基羧酸盐提供了茚异构体和消除产物的复杂混合物。机理测试表明，在这种情况下，末端炔丙基碳酸酯向其丙二烯的互变至多缓慢。
• Tandem Transformations of Nitriles into N-Heterocyclic Compounds by Electrophilic Trapping of Blaise Reaction Intermediates
  作者：Hyunik Shin、Sang-gi Lee、Ju Kim、Yu Chun

  DOI：10.1055/s-0031-1290814

  日期：2012.6

  Tandem transformations of nitriles into various N-heterocycles have been accomplished through the reaction of electrophiles with Blaise reaction intermediates formed in situ. The reaction of the Blaise reaction intermediates with propiolates gives 2-pyridones through consecutive C- and N-nucleophilic reactions. The tandem reactions of the Blaise reaction intermediate with 1,3-enynes proceed through C-nucleophilic addition followed by an electrocyclization-aromatization cascade to give pyridines. Exocyclic enamino esters can be prepared by transformations of omega-chloroalkyl nitriles through chemoselective intramolecular alkylation of the Blaise reaction intermediate. Palladium-catalyzed intramolecular arylations or copper-catalyzed intermolecular cross-coupling reactions of the Blaise reaction intermediate give a range of indole derivatives. Combinations of tandem alkylations and palladium-catalyzed couplings of the Blaise reaction intermediates of omega-chloroalkyl nitriles give N-fused indoles.
• Kleijn,H. et al., Recueil des Travaux Chimiques des Pays-Bas, 1977, vol. 96, p. 251 - 254
  作者：Kleijn,H. et al.

  DOI：——

  日期：——