4-(methylselenyl)butyronitrile | 1357478-88-6

• 分子结构分类: 有机化合物 - 有机金属化合物 - 有机类金属化合物
• 英文名称: 4-(methylselenyl)butyronitrile
• 英文别名: 4-(methylselanyl)butanenitrile；4-(methylseleno)butanenitrile；4-(Methylseleno)butanenitrile；4-methylselanylbutanenitrile
• CAS: 1357478-88-6
• 化学式: C₅H₉NSe
• 分子量: 162.093
• InChiKey: QXCFWBGPRMYUTM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.46
• 重原子数：
  7
• 可旋转键数：
  3
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.8
• 拓扑面积：
  23.8
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  4-(methylselenyl)butyronitrile 在 lithium aluminium tetrahydride 作用下， 以 乙醚 为溶剂， 反应 0.33h， 生成 4-(methylseleno)butamine
  参考文献：
  名称：

  Selenoglucosinolates and their metabolites produced in Brassica spp. fertilised with sodium selenate

  摘要：

  Glucosinolates are sulphur-containing glycosides found in many Brassica spp. that are important because their aglycone hydrolysis products protect the plant from herbivores and exhibit anti-cancer properties in humans. Recently, synthetically produced selenium analogues have been shown to be more effective at suppressing cancers than their sulphur counterparts. Although selenium is incorporated into a number of Brassica amino acids and peptides, firm evidence has yet to be presented for the presence of selenium in the glucosinolates and their aglycones in planta. In this study broccoli and cauliflower florets, and roots of forage rape, all obtained from plants treated with sodium selenate, were analysed for the presence of organoselenides. GC-MS analysis of pentane/ether extracts identified six organoselenium compounds including selenium analogues of known myrosinase-derived Brassica volatiles: 4-(methylseleno)butanenitrile, 5-(methylseleno)pentanenitrile, methylseleno)propylisothiocyanate, 4-(methylseleno)butylisothiocyanate, and 5-(methylseleno)pentylisothiocyanate. LC-MS analysis of ethanolic extracts identified three selenoglucosinolates: methylseleno)propylglucosinolate (glucoselenoiberverin), 4-(methylseleno)butylglucosinolate (glucoselenoerucin), and 5-(methylseleno)pentylglucosinolate (glucoselenoberteroin). LC-MS/MS analysis was used to locate the position of the selenium atom in the selenoglucosinolate and indicates preferential incorporation of selenium via selenomethionine into the methylselenyl moiety rather than into the sulphate or 0-thioglucose groups. In forage rape, selenoglucosinolates and their aglycones (mainly isothiocyanates), occurred at concentrations up to 10% and 70%, respectively, of their sulphur analogues. In broccoli, concentrations of the selenoglucosinolates and their aglycones (mainly nitriles) were up to 60% and 1300%, respectively of their sulphur analogues. These findings indicate the potential for the incorporation of high levels of selenium into Brassica glucosinolates. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.phytochem.2011.11.021
• 作为产物：
  描述：

  二甲基硒 、 4-溴丁腈 在 sodium tetrahydroborate 作用下， 以 乙醇 为溶剂， 反应 2.58h， 以50%的产率得到4-(methylselenyl)butyronitrile
  参考文献：
  名称：

  Selenoglucosinolates and their metabolites produced in Brassica spp. fertilised with sodium selenate

  摘要：

  Glucosinolates are sulphur-containing glycosides found in many Brassica spp. that are important because their aglycone hydrolysis products protect the plant from herbivores and exhibit anti-cancer properties in humans. Recently, synthetically produced selenium analogues have been shown to be more effective at suppressing cancers than their sulphur counterparts. Although selenium is incorporated into a number of Brassica amino acids and peptides, firm evidence has yet to be presented for the presence of selenium in the glucosinolates and their aglycones in planta. In this study broccoli and cauliflower florets, and roots of forage rape, all obtained from plants treated with sodium selenate, were analysed for the presence of organoselenides. GC-MS analysis of pentane/ether extracts identified six organoselenium compounds including selenium analogues of known myrosinase-derived Brassica volatiles: 4-(methylseleno)butanenitrile, 5-(methylseleno)pentanenitrile, methylseleno)propylisothiocyanate, 4-(methylseleno)butylisothiocyanate, and 5-(methylseleno)pentylisothiocyanate. LC-MS analysis of ethanolic extracts identified three selenoglucosinolates: methylseleno)propylglucosinolate (glucoselenoiberverin), 4-(methylseleno)butylglucosinolate (glucoselenoerucin), and 5-(methylseleno)pentylglucosinolate (glucoselenoberteroin). LC-MS/MS analysis was used to locate the position of the selenium atom in the selenoglucosinolate and indicates preferential incorporation of selenium via selenomethionine into the methylselenyl moiety rather than into the sulphate or 0-thioglucose groups. In forage rape, selenoglucosinolates and their aglycones (mainly isothiocyanates), occurred at concentrations up to 10% and 70%, respectively, of their sulphur analogues. In broccoli, concentrations of the selenoglucosinolates and their aglycones (mainly nitriles) were up to 60% and 1300%, respectively of their sulphur analogues. These findings indicate the potential for the incorporation of high levels of selenium into Brassica glucosinolates. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.phytochem.2011.11.021

文献信息

• Additive‐Free Generation of Cyanoalkyl Radicals via Photoinduced Single Electron Transfer from Dichalcogenides to Cycloketone Oxime Esters
  作者：Xiao‐Di Su、Bei‐Bei Zhang、Qiang Liu、Zhu‐Sheng Yang、Zhi‐Xiang Wang、Xiang‐Yu Chen

  DOI：10.1002/ejoc.202200890

  日期：2022.11.7

  A photoactive charge transfer complex protocol for the generation of cyanoalkyl radicals from cyclobutanone oxime esters with dichalcogenides is established.

  建立了从环丁酮肟酯与二硫属化物生成氰烷基自由基的光活性电荷转移复合物方案。
• 一种有机硒化合物的合成方法
  申请人：西南石油大学

  公开号：CN114805163A

  公开（公告）日：2022-07-29

  本发明属于合成药物化学技术领域，具体涉及一种有机硒化合物的合成方法。本发明在温和的条件下，以γ,δ‑不饱和肟酯与环酮肟酯(包括γ,δ‑不饱和肟酯衍生物与环酮肟酯衍生物)为原料，以二硒化物为硒化试剂，以廉价过渡金属镍或铁为催化剂，以实现γ,δ‑不饱和肟酯的氨基硒化与环酮肟酯的氰烷基硒化，从而制备出一系列有机硒吡咯啉衍生物与有机硒烷基腈衍生物。本发明不仅产物的收率高，反应条件温和，原料普遍适用性好，而且催化剂廉价易得，扩大量反应仍能表现出较好的重现性。因此，本发明为今后包含此结构的其他高价值化合物的工业化生产提供了一种有效的方案。