1-selenocarbamoylpiperidine | 61934-60-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 哌啶类
• 英文名称: 1-selenocarbamoylpiperidine
• 英文别名: Piperidine-1-carboximidoselenoic acid；piperidine-1-carboximidoselenoic acid
• CAS: 61934-60-9
• 化学式: C₆H₁₂N₂Se
• 分子量: 191.135
• InChiKey: XXZIQFQUTMFDSM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.31
• 重原子数：
  9
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.83
• 拓扑面积：
  27.1
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  1-selenocarbamoylpiperidine 在 cesium fluoride 作用下， 以 乙腈 为溶剂， 反应 19.0h， 生成 2-piperidin-1-yl-4H-1,3-benzoselenazine
  参考文献：
  名称：

  Rao, U. Narasimha; Sathunuru, Ramadas; Biehl, Edward R., Heterocycles, 2004, vol. 63, # 5, p. 1067 - 1075

  摘要：

  DOI：
• 作为产物：
  描述：

  chloropiperidylformiminium chloride 在 LiAlHSeH 作用下， 以 四氢呋喃 为溶剂， 反应 3.0h， 以91%的产率得到1-selenocarbamoylpiperidine
  参考文献：
  名称：

  由氰胺制备N，N-未取代的硒脲和硫脲

  摘要：

  在乙醚中的HCl存在下，氰酰胺与LiAlHSeH和LiAlHSH反应，分别以中等至高收率提供了相应的N，N-未取代的硒脲和硫脲。

  DOI：

  10.1016/s0040-4039(01)01251-5
• 作为试剂：
  描述：

  methyl [phenyl 4,7,8-tri-O-acetyl-9-O-chloroacetyl-5-(2,2,2-trichloroethoxycarbamoyl)-3,5-dideoxy-2-thio-D-glycero-β-D-galacto-2-nonulopyranosid]onate 在 1-selenocarbamoylpiperidine 、 溶剂黄146 、 三乙胺 、 锌 、 2,4,6-三叔丁基嘧啶 作用下， 以 四氢呋喃 、 1,2-二氯乙烷 、 N,N-二甲基甲酰胺 、 乙腈 为溶剂， 反应 12.0h， 生成
  参考文献：
  名称：

  First Synthesis of a Pentasaccharide Moiety of Ganglioside GAA-7 Containing Unusually Modified Sialic Acids through the Use of N-Troc-sialic Acid Derivative as a Key Unit

  摘要：

  The pentasaccharide part of the potent neuritogenic ganglioside GAA-7 has been synthesized for the first time. The unique branched terminus constituting partially modified sialic acids and N-acetylgalactosamine was successfully established by stereoselective double-sialylation using 8-O-methyl-N-Troc-sialic acid as a donor. The final 4 + 1 coupling reaction provided a high yield of pentasaccharide, which was deprotected to deliver the target molecule.

  DOI：

  10.1021/ol303122w

文献信息

• Facile Preparation of 2-Imino-1,3-selenazolidin-4-one Derivatives by Reaction of <b><i>N</i></b>,<b><i>N’</i></b>-Disubstituted Selenoureas with α-Haloacyl Halides
  作者：Mamoru Koketsu、Hideharu Ishihara、Futoshi Nada

  DOI：10.1055/s-2002-19800

  日期：——

  2-Imino-1,3-selenazolidin-4-one derivatives were synthesized by the reaction of N,N'-disubstituted selenoureas with u-haloacyl halides in the presence of pyridine.

  2-Imino-1,3-selenazolidin-4-one 衍生物是由N,N'-二取代硒脲与u-卤代酰卤在吡啶存在下反应合成的。
• PREPARATION AND CHARACTERISATION OF <i>N,N</i>-DISUBSTITUTED 2-AMINO-SELENAZOLES
  作者：Dietmar Keil、Horst Hartmann

  DOI：10.1080/10426509908031628

  日期：1999.9.1

  Abstract As a result of checking suited methods for preparing N,N-disubstituted 2-amino-selenazoles 14 as a nearly unknown class of highly reactive selenazoles a simple route starting from N,N-disubstituted selenoureas 12 has been elaborated and used for the synthesis of a series of these compounds. The necessary selenium-containing starting compounds 12 are available from N,N-disubstituted cyanamides

  摘要 作为一种几乎未知的高反应性硒唑类 N,N-二取代 2-氨基硒唑 14 制备方法的结果，已经制定了一条从 N,N-二取代硒脲 12 开始的简单路线并用于合成一系列这些化合物。必要的含硒起始化合物12可得自N，N-二取代的氰胺18和硒化氢。
• Synthesis of 2-Amino-1,3-selenazoles by Reaction of N,N-Unsubstituted Selenoureas with a,b-Unsaturated Aldehydes
  作者：Mamoru Koketsu、Koichi Kanoh、Hideharu Ishihara

  DOI：10.3987/com-06-10893

  日期：——

  2-Dialkylamino-l,3-selenazoles were obtained by the reaction of N,N-unsubstituted selenoureas with α,β-unsaturated aldehydes in alcohol in the presence of ferric chloride at room temperature.

  2-二烷基氨基-1,3-硒唑是由N,N-未取代的硒脲与α,β-不饱和醛在氯化铁存在下室温反应得到。
• A Simple Route to <i>N</i>,<i>N</i>-Disubstituted Selenoureas from N,N-Disubstituted Cyanamides­
  作者：Horst Hartmann、Dietmar Keil

  DOI：10.1055/s-2003-44349

  日期：——

  N,N-Disubstituted selenoureas 4 can be obtained in satisfactory yields by addition of an acid to a mixture of freshly prepared sodium selenide and N,N-disubstituted cyanamides 5.

  N,N-二取代的硒脲 4 可以通过将酸添加到新制备的硒化钠和 N,N-二取代的氰胺 5 的混合物中以令人满意的收率获得。
• Inhibition of Tyrosinase Activity by N,N-Unsubstituted Selenourea Derivatives
  作者：Sang Keun Ha、Mamoru Koketsu、Kunho Lee、Sang Yoon Choi、Ji-Ho Park、Hideharu Ishihara、Sun Yeou Kim

  DOI：10.1248/bpb.28.838

  日期：——

  This study investigated inhibitory effects of N,N-unsubstituted selenourea derivatives on tyrosinase activity. Three types of N,N-unsubstituted selenoureas derivatives exhibited inhibitory effect on dopa (3,4-dihydroxyphenylalanine) oxidase activity of mushroom tyrosinase. Compound D at a concentration of 200 μM exhibited 55.5% of inhibition on dopa oxidase activity of mushroom tyrosinase. This inhibitory effect was higher than that of kojic acid (39.4%), a well known tyrosinase inhibitor. Moreover, the compound D identified as a noncompetitive inhibitor by Lineweaver–Burk plot analysis. In addition, compound D also inhibited the melanin production in melan-a cells.

  本研究探讨了 N,N-未取代硒脲衍生物对酪氨酸酶活性的抑制作用。三种 N,N-未取代硒脲衍生物对蘑菇酪氨酸酶的多巴（3,4-二羟基苯丙氨酸）氧化酶活性有抑制作用。浓度为 200 μ<小>M的化合物 D 对蘑菇酪氨酸酶多巴氧化酶活性的抑制率为 55.5%。这种抑制效果高于众所周知的酪氨酸酶抑制剂曲酸（39.4%）。此外，化合物 D 通过 Lineweaver-Burk plot 分析被确定为一种非竞争性抑制剂。此外，化合物 D 还能抑制黑色素-a 细胞中黑色素的生成。