2-(2,2-二乙氧基乙基二硒)-1,1-二乙氧基乙烷 | 90466-79-8

• 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
• 中文名称: 2-(2,2-二乙氧基乙基二硒)-1,1-二乙氧基乙烷
• 英文名称: 1,2-bis(2,2-diethoxyethyl)diselane
• 英文别名: bis(2,2-diethoxyethyl) diselenide；bis(2,2-diethoxyethyl)diselenide；Diselenide, bis(2,2-diethoxyethyl)-；2-(2,2-diethoxyethyldiselanyl)-1,1-diethoxyethane
• CAS: 90466-79-8
• 化学式: C₁₂H₂₆O₄Se₂
• 分子量: 392.256
• InChiKey: DNYWGZLSHKFTRS-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.94
• 重原子数：
  18
• 可旋转键数：
  13
• 环数：
  0.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  36.9
• 氢给体数：
  0
• 氢受体数：
  4

制备方法与用途

类别：有毒物品
毒性分级：剧毒
急性毒性：静脉-小鼠 LD50: 1.8 毫克/公斤
可燃性危险特性：可燃；受热产生有毒硒氧化物烟雾
储运特性：库房通风低温干燥；与食品原料分开存放
灭火剂：干粉、泡沫、沙土、二氧化碳、雾状水
职业标准：TWA 0.2 毫克/立方米

反应信息

• 作为反应物：
  描述：

  2-(2,2-二乙氧基乙基二硒)-1,1-二乙氧基乙烷 在 甲酸 作用下， 反应 1.0h， 生成 bis(2-oxoethyl)diselenide
  参考文献：
  名称：

  二硒化物与双（N，N-二烷基硒代氨基甲酰基）硒化物之间的新型交换反应。在四硒富勒烯（TSF）合成中的应用

  摘要：

  报道了高产率合成四硒富勒烯（TSF），涉及二硒化物与双（N，N-二烯丙基硒代氨基甲酰基）硒化物之间的新型酸催化的交换反应。

  DOI：

  10.1039/c39840000089
• 作为产物：
  描述：

  2-溴-1,1-二乙氧基乙烷 在 potassium selenocyanate 、 potassium carbonate 作用下， 以 N,N-二甲基甲酰胺 、 水 为溶剂， 反应 8.0h， 生成 2-(2,2-二乙氧基乙基二硒)-1,1-二乙氧基乙烷
  参考文献：
  名称：

  Direct synthesis of sensitive selenocysteine peptides by the Ugi reaction

  摘要：

  氨和硒醛都是 Ugi 反应中的问题成分。在此，我们报告了在不使用可转化（保护）伯胺的情况下直接多组分合成敏感硒半胱氨酸肽的高效方法，包括硒醇的合适脱保护方案。

  DOI：

  10.1039/c2ob26552d

文献信息

• Lithium diselenide in aprotic medium - a convenient reagent for synthesis of organic diselenides
  作者：Ludwik Syper、Jacek Mlochowski

  DOI：10.1016/s0040-4020(01)89801-x

  日期：1988.1

  The reduction of selenium with lithium in THF in the presence of diphenylacetylene as a catalyst afforded lithium diselenide, which reacted with electrophiles giving alkyl or aryl diselenides 1 - 3 and selenides 4, as by-products. The useful method for preparation of diselenides based on this reaction was elaborated.

  在二苯乙炔作为催化剂的存在下，用锂在THF中还原硒，得到二硒化锂，其与亲电试剂反应生成副产物烷基或芳基二硒化物1-3和硒化物4。阐述了基于该反应制备二硒化物的有用方法。
• One pot synthesis of selenocysteine containing peptoid libraries by Ugi multicomponent reactions in water
  作者：Muhammad Abbas、John Bethke、Ludger A. Wessjohann

  DOI：10.1039/b514597j

  日期：——

  Selenocysteine containing peptoids and peptide–peptoid conjugates were synthesized by combinatorial Ugi-MCRs (multicomponent reactions) in water: for the first time, an acetal (selenoacetal 2a) was used in Ugi-MCR to furnish selenocysteine peptoids in one step as model compounds for selenocysteine peptides and proteins.

  在水中通过组合式 Ugi-MCR（多组分反应）合成了含硒半胱氨酸的类肽和肽-类肽结合物：首次在 Ugi-MCR 中使用缩醛（硒乙缩醛 2a），一步生成硒半胱氨酸类肽，作为硒半胱氨酸肽和蛋白质的模型化合物。
• Catalysis of Thiol–Thioester Exchange by Water-Soluble Alkyldiselenols Applied to the Synthesis of Peptide Thioesters and SEA-Mediated Ligation
  作者：Marine Cargoët、Vincent Diemer、Benoît Snella、Rémi Desmet、Annick Blanpain、Hervé Drobecq、Vangelis Agouridas、Oleg Melnyk

  DOI：10.1021/acs.joc.8b01903

  日期：2018.10.19

  N-Alkyl bis(2-selanylethyl)amines catalyze the synthesis of peptide thioesters or peptide ligation from bis(2-sulfanylethyl)amido (SEA) peptides. These catalysts are generated in situ by reduction of the corresponding cyclic diselenides by tris(2-carboxyethyl)phosphine. They are particularly efficient at pH 4.0 by accelerating the thiol–thioester exchange processes, which are otherwise rate-limiting

  N-烷基双（2-硒基乙基）胺催化双（2-硫烷基乙基）酰胺基（SEA）肽的硫代酸酯的合成或肽的连接。这些催化剂通过用三（2-羧乙基）膦还原相应的环状二硒化物而原位产生。通过加速硫醇-硫酯交换过程，它们在pH 4.0时特别有效，否则在该pH值下会受到速率的限制。通过在弱酸性pH值下促进SEA介导的反应，它们有助于合成复杂的肽，例如很难通过其他途径获得的环状O-酰基异肽。
• Multicomponent reactions for the synthesis of multifunctional agents with activity against cancer cells
  作者：Saad Shabaan、Lalla A. Ba、Muhammad Abbas、Torsten Burkholz、Annika Denkert、André Gohr、Ludger A. Wessjohann、Florenz Sasse、Wolfgang Weber、Claus Jacob

  DOI：10.1039/b823149d

  日期：——

  Multicomponent Passerini and Ugi reactions enable the fast and efficient synthesis of redox-active multifunctional selenium and tellurium compounds, of which some show considerable cytotoxicity against specific cancer cells.

  多组分 Passerini 和 Ugi 反应能够快速高效地合成具有氧化还原作用的多功能硒和碲化合物，其中一些化合物对特定癌细胞具有相当强的细胞毒性。
• Synthesis and Selective Anticancer Activity of Organochalcogen Based Redox Catalysts
  作者：Mandy Doering、Lalla A. Ba、Nils Lilienthal、Carole Nicco、Christiane Scherer、Muhammad Abbas、Abdul Ali Peer Zada、Romain Coriat、Torsten Burkholz、Ludger Wessjohann、Marc Diederich、Frederic Batteux、Marco Herling、Claus Jacob

  DOI：10.1021/jm100576z

  日期：2010.10.14

  Many tumor cells exhibit a disturbed intracellular redox state resulting in higher levels of reactive oxygen species (ROS). As these contribute to tumor initiation and sustenance, catalytic redox agents combining significant atctivity with substrate specificity promise high activity andselectivity L. Must oxidatively stressed malignant cells. We describe here the design and synthesis of novel organochalcogen based redox sensor/effector catalysts. Their selective anticancer activity at submicromolar and low micromolar concentrations was established here in a range of tumor entities in various biological systems including cell lines, primary tumor cell cultures, and animal models. In the B-cell derived chronic lymphocytic leukemia (CLL), for instance, such compounds preferentially induce apoptosis in the cancer cells while peripheral blood mononuclear cells (PBMC) from healthy donors and the subset of normal 13-cells remain largely unaffected. In support of the concept of sensor/effector based ROS amplification, we are able to demonstrate that underlying this selective activity against CI.I. cells are pre-existing, elevated ROS levels in the leukemic cells compared to their nonmalignant counterparts. Furthermore, the catalysts act in concert with certain chemotherapeutic drugs in several carcinoma cell lines to decrease cell proliferation while showing no such interactions in normal cells. Overall, the high efficacy and selectivity of. (redox) catalytic sensor/effector compounds warrant further, extensive testing toward transfer into the clinical arena.