5-thiocyanatopent-1-ene | 20243-54-3

• 分子结构分类: 有机化合物 - 有机硫化合物
• 英文名称: 5-thiocyanatopent-1-ene
• 英文别名: 1-Pentenyl thiocyanate；4-pentenyl thiocyanate；pent-4-enyl thiocyanate
• CAS: 20243-54-3
• 化学式: C₆H₉NS
• mdl: MFCD08457797
• 分子量: 127.21
• InChiKey: DDXWRFXSAYFRRE-UHFFFAOYSA-N

物化性质

• 沸点：
  196.9±19.0 °C(Predicted)
• 密度：
  0.978±0.06 g/cm3(Predicted)
• LogP：
  2.550 (est)

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  8
• 可旋转键数：
  4
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  49.1
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  5-thiocyanatopent-1-ene 在 Hoveyda-Grubbs catalyst second generation 作用下， 以 二氯甲烷 为溶剂， 反应 0.5h， 以45 mg的产率得到1,8-dithiocyanatooct-4-ene
  参考文献：
  名称：

  Microwave-Assisted Cross-Metathesis of Unsaturated Thiocyanates: Application to the Synthesis of Thiocyanatins A and B and Analogues

  摘要：

  硫氰酸铂 B 和相关二硫代氰酸酯的合成是通过不饱和硫氰酸盐在钌催化剂的促进下进行交叉偏析来实现的。反应的效率在很大程度上取决于催化剂的性质、烯基链的长度和活化方式（传统加热或微波活化）。在后一种情况下，双键发生了异构化，改变了反应的进程。另外，硫氰酸盐 A 和 B 也分别只需三步和两步就能从现成的对甲苯磺酸盐中合成。

  DOI：

  10.1055/s-0029-1217089
• 作为产物：
  描述：

  sodium thiocyanide 、 5-溴-1-戊烯 生成 5-thiocyanatopent-1-ene
  参考文献：
  名称：

  The Potential of Semiochemicals for Control ofPhorodon humuli(Homoptera: Aphididae)

  摘要：

  Field experiments employing yellow water-traps with vials releasing methyl salicylate, butyl isothiocyanate, 4-pentenyl isothiocyanate and diethyltoluamide were conducted during the spring migration of Phorodon humuli (Schrank), with the aim of identifying substances which might be used in the field to deter landing on hop plants. Methyl salicylate and the two isothiocyanates reduced trap catches of P. humuli. During the spring of 1994 a slow-release formulation of methyl salicylate and a beta-acid-rich hop resin sprayed on to hop plants did not reduce aphid infestations significantly. In autumn cis,cis-nepetalactol the main component of P. humuli's sex pheromone, prepared by various synthetic routes, increased trap catches of males and gynoparae equally. Catches of males in pheromone traps situated in a hop garden decreased with increasing trap height. Catches of males in traps charged with increasing doses of the cis,cis-nepetalactol peaked at 1 mg and then plateaued, whereas catches of gynoparae peaked similarly at 1 mg and then decreased. The effects of kairomones from an extract of the primary host, sex pheromone and a visual cue from yellow compared with clear water-traps were additive. The prospects for developing a semiochemicals-based control strategy against P. humuli, using some or all of the above elements, are discussed.

  DOI：

  10.1002/(sici)1096-9063(199612)48:4<293::aid-ps479>3.0.co;2-5

文献信息

• Trialkyl(alkenylthio)stannanes
  作者：M. G. Voronkov、E. L. Dubinskaya、G. N. Legov、O. S. Stankevich、L. E. Protasova、S. G. Shevchenko、T. N. Aksamentova

  DOI：10.1007/bf00698892

  日期：1993.12

  Previously unknown trialkyl(alkenylthio)stannanes were obtained by the interaction of alkenyl thiocyanates with trialkyl(methoxy)stannanes; some of their properties and transformations were studied.

  以前未知的三烷基（链烯硫基）锡烷是通过链烯基硫氰酸酯与三烷基（甲氧基）锡烷的相互作用获得的；研究了它们的一些性质和转换。
• Structure–Activity Relationship Study on Isothiocyanates: Comparison of TRPA1-Activating Ability between Allyl Isothiocyanate and Specific Flavor Components of Wasabi, Horseradish, and White Mustard
  作者：Yuko Terada、Hideki Masuda、Tatsuo Watanabe

  DOI：10.1021/acs.jnatprod.5b00272

  日期：2015.8.28

  Allyl isothiocyanate (ITC) (4) is the main pungent component in wasabi, and it generates an acrid sensation by activating TRPAL The flavor and pungency of ITCs vary depending on the compound. However, the differences in activity to activate TRPA1 between ITCs are effect of carbon chain length and substituents of ITCs, the not known except for a few compounds. To investigate the TRPA1-activiting ability ITCs was measured. Since most of the ITCs showed nearly equal TRPA1-activiting potency,. the ITC moiety is likely the predominant contributor to their TRPA1-activating abilities, and contributions of other functional groups to their activities to activate TRPA1 are comparatively small.