(Z)-Pent-2-endinitril | 91028-12-5

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: (Z)-Pent-2-endinitril
• 英文别名: Z-glutacononitrile；cis-1,3-Dicyanpropen；(Z)-Glutacinonitril；(Z)-pent-2-enedinitrile
• CAS: 91028-12-5
• 化学式: C₅H₄N₂
• 分子量: 92.1002
• InChiKey: UVNWMIHXIIMNHU-UPHRSURJSA-N

物化性质

• 沸点：
  270.2±23.0 °C(Predicted)
• 密度：
  1.007±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.1
• 重原子数：
  7
• 可旋转键数：
  1
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  47.6
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  1-Aminobuta-1,3-dien-1,4-dicarbonitril 在 quartz 作用下， 440.0 ℃ 、40.0 Pa 条件下， 生成 E-glutacononitrile 、 (Z)-Pent-2-endinitril
  参考文献：
  名称：

  Chemie vonα-氨基三烯。12. Mitteilung。Sondierungenüberthermische Umwandlungen vonα-Aminonitrilen †

  摘要：

  α-氨基腈的化学1 。α-氨基腈热反应的探索性实验

  DOI：

  10.1002/hlca.19940770814

文献信息

• 2-Pyridylnitrene and 3-Pyridazylcarbene and Their Relationship via Ring-Expansion, Ring-Opening, Ring-Contraction, and Fragmentation
  作者：David Kvaskoff、Pawel Bednarek、Curt Wentrup

  DOI：10.1021/jo902570d

  日期：2010.3.5

  photolysis. Nitrenes 19 and 23 were detected by ESR spectroscopy, and cumulene 21 by IR and UV spectroscopy. FVT of 22T/22A also affords 2-pyridylnitrene 19 and diazacycloheptatetraene 21, as well as glutacononitriles 27Z,E and 2- and 3-cyanopyrroles 28 and 29. Photolysis of 21 above 300 nm yields the novel spiroazirene 25, identified by its matrix IR spectrum. The reaction pathways connecting the four

  通过红外光谱检测，在Ar基质中分离的三唑并[1,5- b ]哒嗪8发生光解，生成重氮甲基哒嗪9Z和9E以及重氮戊烯炔11Z和11E。ESR光谱检测到分别由一个和两个N 2分子的损失形成的3-吡啶基卡宾10以及戊-2-烯-3-炔-1-亚基12。进一步的光解作用导致羧甲基重排至1,2-戊二烯-4-炔13和3-乙炔基环丙烯14。闪蒸真空热解（FVT）在400-500°C下为8，并分离出Ar产物13，14，和1,4- pentadiyne 15。在较高温度下，也形成了戊二腈27Z和27E以及少量的2-和3-氰基吡咯28和29。Tetrazolo [1,5- a ]吡啶/ 2-叠氮吡啶22T / 22A产生2-吡啶基硝烯19以及新型的开链氰基二烯基氮杂烯23和环扩环的1,3-二氮杂环庚-1,2,4,6-丁烯21在短波长下光解。氮宾19和23是由ESR光谱，和cumulene检测通过红外和紫外光谱分析21。FVT的22T
• 2-Pyridylnitrene from Tetrazolo[1,5-<i>a</i>]pyridine and Pyrido[2,3-<i>a</i>][1,2,4]oxadiazol-2-one
  作者：Adam McCluskey、Curt Wentrup

  DOI：10.1021/jo800899t

  日期：2008.8.1

  Flash vacuum thermolyses of tetrazolo[1,5-a]pyridine and pyrido[2,3-a][1,2,4]oxadiazol-2-one generate 2-pyridylnitrene, which was detected by Ar matrix ESR spectroscopy. The thermolysis products are 2-aminopyridine, Z- and E-glutacononitriles, and 2- and 3-cyanopyrroles. The products are formed in the same ratios from the two precursors.

  对四唑并[1,5- a ]吡啶和吡啶并[2,3- a ] [1,2,4]恶二唑-2-one进行闪蒸真空热解生成2-吡啶基硝烯，并通过Ar矩阵ESR光谱法对其进行了检测。热分解产物是2-氨基吡啶，Z-和E-戊二腈以及2-和3-氰基吡咯。产物是由两种前体以相同的比例形成的。
• A13C and1H NMR study of the geometries of the 1,3-dicyanoallyl anion: Thermal and photochemical interconversion
  作者：D. R. Boate、D. H. Hunter

  DOI：10.1002/mrc.1270220307

  日期：1984.3

  AbstractGlutacononitrile (1,3‐dicyanopropene) (2) was converted to its anion (1) by treatment with sodium hydride in tetrahydrofuran. Both 13C and 1 NMR showed that the sodium salt of 1 in THF existed in three slowly interconverting geometries (U, W and S). These geometries were present in similar amounts but the relative amounts of each proved to be concentration dependent. Irradiation of a 0.01 M solution of 1 at −80°C led to the conversion of a mixture of the U, W and S forms of 1 to only the W and S forms. Upon warming to 0°C equilibrium was re‐established with a half‐life of approximately 8 h.
• Chemie von ?-Aminonitrilen. 12. Mitteilung. Sondierungen �ber thermische Umwandlungen von ?-Aminonitrilen
  作者：Yi-Bin Xiang、Susanne Drenkard、Karl Baumann、Deirde Hickey、Albert Eschenmoser

  DOI：10.1002/hlca.19940770814

  日期：1994.12.14

  Chemistry of α-Amino Nitriles1 . Exploratory Experiments on Thermal Reactions of α-Amino Nitriles

  α-氨基腈的化学1 。α-氨基腈热反应的探索性实验