2,2-bis(methylseleno)acetaldehyde

• 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: 2,2-bis(methylseleno)acetaldehyde
• 英文别名: bis(methylseleno)acetaldehyde；(MeSe) CHCHO；2,2-Bis(methylselanyl)acetaldehyde
• 化学式: C₄H₈OSe₂
• 分子量: 230.027
• InChiKey: CMIHPYHWCIAORK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.44
• 重原子数：
  7
• 可旋转键数：
  3
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.75
• 拓扑面积：
  17.1
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为产物：
  描述：

  1,1-diethoxy-2-methylselenoethane 在 盐酸 、 水 作用下， 以 四氢呋喃 为溶剂， 反应 96.0h， 以17%的产率得到2,2-bis(methylseleno)acetaldehyde
  参考文献：
  名称：

  3-亚甲基四氢呋喃-2-酮衍生物的简便合成方法及相关体系

  摘要：

  使用Shapiro反应，由两个酮或醛和酮与二氧化碳缩合，在“一锅”中制备标题化合物。例如，依次用正丁基锂（–50°C），丙酮（–50°C），正丁基锂（–78至0至– 78°C），二氧化碳（–78°C）和三氟乙酸（25°C）生成5,5-二甲基-3-亚甲基四氢呋喃-2-酮。扩展反应以制备3-亚甲基四氢吡喃-2-酮和3，5-二亚甲基四氢呋喃-2-酮的衍生物。

  DOI：

  10.1039/p19810002848

文献信息

• Organoselenides from Nicotiana tabacum genetically modified to accumulate selenium
  作者：Adam J. Matich、Marian J. McKenzie、David A. Brummell、Daryl D. Rowan

  DOI：10.1016/j.phytochem.2009.06.001

  日期：2009.6

  Nicotiana tabacum L. (tobacco) plants were transformed to overexpress a selenocysteine methyltransferase gene from the selenium hyperaccumulator Astragalus bisulcatus (Hook.) A. Gray (two-grooved milk-vetch), and an ATP-sulfurylase gene from Brassica oleracea L. var. italica (broccoli). Solvent extraction of leaves harvested from plants treated with selenate revealed five selenium-containing compounds, of which four were identified by chemical synthesis as 2-(methylseleno)acetaldehyde, 2,2-bis(methylseleno)acetaldehyde, 4-(methylseleno)-(2E)-nonenal, and 4-(methylseleno)-(2E,6Z)-nonadienal. These four compounds have not previously been reported in nature. (C) 2009 Elsevier Ltd. All rights reserved.
• Selenoglucosinolates and their metabolites produced in Brassica spp. fertilised with sodium selenate
  作者：Adam J. Matich、Marian J. McKenzie、Ross E. Lill、David A. Brummell、Tony K. McGhie、Ronan K.-Y. Chen、Daryl D. Rowan

  DOI：10.1016/j.phytochem.2011.11.021

  日期：2012.3

  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.
• ADLINGTON, R. M.;BARRETT, A. G. M., J. CHEM. SOC. PERKIN TRANS., 1981, N 11, 2848-2863
  作者：ADLINGTON, R. M.、BARRETT, A. G. M.

  DOI：——

  日期：——
• Concise syntheses of 3-methylenetetrahydrofuran-2-one derivatives and related systems
  作者：Robert M. Adlington、Anthony G. M. Barrett

  DOI：10.1039/p19810002848

  日期：——

  Using the Shapiro reaction, the title compounds were prepared in ‘one pot’ from the condensation of two ketones, or an aldehyde and a ketone, with carbon dioxide. For example, acetone 2,4,6-tri-isopropylbenzenesulphonylhydrazone was treated in sequence with n-butyl-lithium (–50 °C), acetone (–50 °C), n-butyl-lithium (–78 to 0 to –78 °C), carbon dioxide (–78 °C), and trifluoroacetic acid (25 °C) to

  使用Shapiro反应，由两个酮或醛和酮与二氧化碳缩合，在“一锅”中制备标题化合物。例如，依次用正丁基锂（–50°C），丙酮（–50°C），正丁基锂（–78至0至– 78°C），二氧化碳（–78°C）和三氟乙酸（25°C）生成5,5-二甲基-3-亚甲基四氢呋喃-2-酮。扩展反应以制备3-亚甲基四氢吡喃-2-酮和3，5-二亚甲基四氢呋喃-2-酮的衍生物。