N,N-dimethyl-selenoacetamide | 25355-77-5

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: N,N-dimethyl-selenoacetamide
• 英文别名: N,N-dimethylselenoacetamide；N,N-dimethylethaneselenoamide
• CAS: 25355-77-5
• 化学式: C₄H₉NSe
• 分子量: 150.082
• InChiKey: RAEXYNFSJGRHJB-UHFFFAOYSA-N

物化性质

• 熔点：
  84.5 °C(Solv: hexane (110-54-3))
• 沸点：
  134.6±23.0 °C(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -0.13
• 重原子数：
  6
• 可旋转键数：
  1
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.75
• 拓扑面积：
  3.2
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  N,N-dimethyl-selenoacetamide 、 碘甲烷 生成 N,N,S-Trimethyl-selenoacetamidinium
  参考文献：
  名称：

  Jensen,K.A.; Nielsen,P.H., Acta Chemica Scandinavica (1947), 1966, vol. 20, p. 597 - 629

  摘要：

  DOI：
• 作为产物：
  描述：

  N,N-二甲基乙酰胺 在 bis(1,5-cyclooctanediylboryl)monoselenide 作用下， 以 二氯甲烷 、 均三甲苯 为溶剂， 反应 5.0h， 以34%的产率得到N,N-dimethyl-selenoacetamide
  参考文献：
  名称：

  An Efficient Synthesis of Selenocarbonyl Compounds by the Treatment of Carbonyl Compounds with Bis[1,5-cyclooctanediylboryl] Selenide

  摘要：

  通过使用双[1,5-环辛二基硼烷]硒化物处理羰基化合物，实现了硒醛、硒酮和硒酰胺的高效合成。

  DOI：

  10.1246/cl.1992.1843

文献信息

• Acyclic Selenoiminium Salts:  Isolation, First Structural Characterization, and Reactions
  作者：Yuichiro Mutoh、Toshiaki Murai

  DOI：10.1021/ol034334f

  日期：2003.4.1

  [reaction: see text] A variety of selenoiminium salts were obtained by reacting the corresponding selenoamides with methyl triflate at room temperature for 30 s. All of the salts were stable under air. The structures of the selenoiminium salts were determined by X-ray molecular analysis. An aromatic selenoiminium salt reacted with BuLi (3 equiv) to give two types of ketones. In a reaction with LiAlH(4)/Te

  [反应：见正文]通过使相应的硒酰胺与三氟甲磺酸甲酯在室温下反应30 s，可获得多种硒亚胺盐。所有的盐在空气中都是稳定的。硒亚胺盐的结构通过X射线分子分析确定。芳香族硒亚胺盐与BuLi（3当量）反应生成两种类型的酮。在与LiAlH（4）/ Te的反应中，硒亚胺盐被转化为碲酰胺。
• Reaction of diisobutylaluminium hydride with selenium and tellurium: new reagents for the synthesis of seleno- and telluro-amides
  作者：Guang Ming Li、Ralph A. Zingaro

  DOI：10.1039/a707792k

  日期：——

  Diisobutylaluminium hydride (Bui2AlH) undergoes reaction with elemental selenium and tellurium to afford new reagents having an Al–Se or an Al–Te bond. These directly convert amides to selenoamides and telluroformamides. This affords a one-pot route to selenoamides and telluroformamides starting from Se and Te, and may be suitable for large scale syntheses.

  二异丁基铝氢（Bui2AlH）与元素硒和碲反应，生成具有Al-Se或Al-Te键的新试剂。这些试剂可以直接将酰胺转化为硒酰胺和碲酰亚胺。这提供了一条从硒和碲出发，一步制备硒酰胺和碲酰亚胺的一锅法路线，可能适用于大规模合成。
• MeOTf-Mediated Alkynylation of Selenoamides Leading to β-Methylselenenyl α,β-Unsaturated Ketones and Their Characterization
  作者：Toshiaki Murai、Yuichiro Mutoh、Shinzi Kato

  DOI：10.1021/ol015968u

  日期：2001.6.1

  [reaction: see text] beta-Methylselenenyl alpha,beta-unsaturated ketones were effectively synthesized by treating selenoamides with methyl triflate, followed by reaction with lithium acetylides. The reaction proceeded with high stereoselectivity to give exclusively Z-isomers. (77)Se NMR studies and X-ray molecular structure analysis of beta-methylselenenyl alpha,beta-unsaturated ketones suggested that

  [反应：见正文]通过用三氟甲磺酸甲酯处理硒酰胺，然后与乙炔化锂反应，可以有效地合成β-甲基硒烯基α，β-不饱和酮。反应以高立体选择性进行，仅得到Z-异构体。（77）Se NMR研究和β-甲基硒烯α，β-不饱和酮的X射线分子结构分析表明，该产品显示出硒原子和羰基氧原子之间的1,5-非键相互作用。
• Efficient Synthesis of Selenocarbonyl Compounds by Treating Carbonyl Compounds with Bis(1,5-cyclooctanediylboryl) Selenide
  作者：Kazuaki Shimada、Norikazu Jin、Michiko Kawaguchi、Kumiko Dobashi、Yumi Nagano、Manabu Fujimura、Eiichi Kudoh、Tomonari Kai、Noboru Saito、Jun-ichi Masuda、Masaki Iwaya、Hiroyuki Fujisawa、Shigenobu Aoyagi、Yuji Takikawa

  DOI：10.1246/bcsj.70.197

  日期：1997.1

  Selenoaldehydes and selenoketones were generated in situ, by treating aldehydes or ketones, respectively, with bis(1,5-cyclooctanediylboryl) selenide; the resulting selenocarbonyl compounds were trapped with 2,3-dimethyl-1,3-butadiene to give the corresponding [4+2] cycloadducts. The treatment of amides, an ester, and ketones possessing bulky substituents with the reagent also afforded the corresponding selenoamides, a selenoester, and sterically protected selones, respectively, in modest yields. On the other hand, a similar treatment of cinnamaldehyde with the reagent gave the 2,3-dihydroselenophene derivative, which originated from a [4+2]-type self-dimerization of in situ generated 3-phenyl-2-propeneselenal.

  在原位生成硒醛和硒酮，通过将醛或酮与双(1,5-环辛烷二基)硒化物处理；由此得到的硒羰基化合物与2,3-二甲基-1,3-丁二烯反应，形成相应的[4+2]环加成物。将具有体积较大取代基的酰胺、酯和酮与该试剂处理，亦分别得到相应的硒酰胺、硒酯和体积保护的硒酮，产率适中。另一方面，将肉桂醛与该试剂处理，得到2,3-二氢硒苯衍生物，这源于原位生成的3-苯基-2-丙烯硒醛的[4+2]型自聚合反应。
• Conversion of Amides,<i>N</i>,<i>N</i>,<i>N</i>′,<i>N</i>′-Tetramethylurea, and Esters to the Corresponding Selenoxo Compounds by Treatment with Bis(trimethylsilyl) Selenide and BF₃·OEt₂
  作者：Yuji Takikawa、Hiroyuki Watanabe、Ryuji Sasaki、Kazuaki Shimada

  DOI：10.1246/bcsj.67.876

  日期：1994.3

  The reactions of amides and N,N,N′,N′-tetramethylurea with (Me3Si)2Se in the presence of BF3·OEt2 afforded the corresponding slelenoxo compounds in good yields. On the other hand, selenation of ethyl and butyl benzoates in a similar manner gave benzoin and 2,3,5,6-tetraphenyl-1,4-diselenin via selenoesters. The trapping of selenoesters was also achieved by 2,3-dimethyl-1,3-butadiene to afford [4+2] cycloadducts.

  酰胺和N,N,N′,N′-四甲基尿素与(Me3Si)2Se在BF3·OEt2存在下反应，得到相应的硒氧化合物，产率良好。另一方面，以类似方式对乙基和丁基苯甲酸酯进行硒化，得到了苯醇和2,3,5,6-四苯基-1,4-二硒烯，反应通过硒酯实现。通过2,3-二甲基-1,3-丁二烯捕获硒酯也成功地得到[4+2]环加成产物。