1,4-bis(trimethylsilyl)-2,5-piperazinedione | 3553-95-5

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: 1,4-bis(trimethylsilyl)-2,5-piperazinedione
• 英文别名: 2,5-Piperazinedione, 1,4-bis(trimethylsilyl)-；1,4-bis(trimethylsilyl)piperazine-2,5-dione
• CAS: 3553-95-5
• 化学式: C₁₀H₂₂N₂O₂Si₂
• 分子量: 258.468
• InChiKey: AGYQHDRWVGBTKU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.33
• 重原子数：
  16
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.8
• 拓扑面积：
  40.6
• 氢给体数：
  0
• 氢受体数：
  2

安全信息

• 海关编码：
  2933599090

反应信息

• 作为反应物：
  描述：

  氯甲基二甲基氯硅烷 、 1,4-bis(trimethylsilyl)-2,5-piperazinedione 以 苯 为溶剂， 反应 3.0h， 以69%的产率得到1,4-bis(dimethylchlorosilylmethyl)-2,5-piperazinedione
  参考文献：
  名称：

  Shipov, A. G.; Artamkina, O. B.; Kramarova, E. P., Journal of general chemistry of the USSR, 1991, vol. 61, # 8.2, p. 1770 - 1771

  摘要：

  DOI：
• 作为产物：
  描述：

  甘氨酸酐 、 N,O-双(三甲基硅烷基)三氟乙酰胺 以 乙腈 为溶剂， 以90%的产率得到1,4-bis(trimethylsilyl)-2,5-piperazinedione
  参考文献：
  名称：

  Study of Binuclear Silicon Complexes of Diketopiperazine at S_N2 Reaction Profile

  摘要：

  A series of binuclear pentacoordinate silicon complexes of diketopiperazine have been synthesized and substituent (leaving group) effects on the Si-O bond coordination have been studied by comparison of the five differently substituted analogous structures (X = F, Cl, OTf, Br, and I). Variable-temperature NMR spectroscopy supported by X-ray crystallography shows, for the first time in binuclear pentacoordinate silicon complexes, a complex equilibrium with both nonionic (O-Si) and ionic (Si-X) dissociation of the axial bonds in the silicon-centered trigonal bipyramids. The two dissociation pathways are consistent with a model for nucleophilic substitution in a binuclear pentacoordinate silicon compound at the silicon atom.

  DOI：

  10.1021/om1009318

文献信息

• N-[difluoro(methyl)silyl]carboxamides: Synthesis, structural features and theoretical estimating of Si←O dative bond energy
  作者：Nataliya F. Lazareva、Irina V. Sterkhova、Alexander V. Vashchenko

  DOI：10.1016/j.molstruc.2020.129130

  日期：2021.2

  original method of the synthesis of N-[difluoro(methyl)silyl]methylcarboxamides and related compounds based on the reaction of alkylation of N-trimethylsilyl derivatives by bifunctional silane ClCH2SiF2Me was use to prepare of N-[difluoro(methyl)silyl]methyl}-N-methylacetamide, N-[difluoro-(methyl)silyl]methyl}benzanilide and phenyl-N-phenyl-N-[difluoro(methyl)silyl]methyl}carbamate. The structures

  摘要 采用双官能硅烷 ClCH2SiF2Me 对 N-三甲基甲硅烷基衍生物进行烷基化反应，合成 N-[二氟（甲基）甲硅烷基]甲基甲酰胺及相关化合物的新方法，制备了 N-[二氟（甲基）甲硅烷基]甲硅烷基]甲基}-N-甲基乙酰胺、N-[二氟-(甲基)甲硅烷基]甲基}苯甲酰苯胺和苯基-N-苯基-N-[二氟(甲基)甲硅烷基]甲基}氨基甲酸酯。这些化合物的结构通过 NMR、FTIR 和 X 射线分析确认。根据 X 射线分析数据，所研究化合物中配位键 C=O→Si 的长度分别为 1.969、2.000 和 2.176 A。Si-Fax 的长度。分别包括 1.686、1.661 和 1.632 A。QTAIM 分析用于估计这些酰胺中配位键 C=O→Si 的能量。
• Synthesis and Antiviral Properties of Arabino and Ribonucleosides of 1,3‐Dideazaadenine, 4‐Nitro‐1, 3‐dideazaadenine and Diketopiperazine
  作者：Sarika Sinha、Richa Srivastava、Erik De Clercq、Ramendra K. Singh

  DOI：10.1081/ncn-200040614

  日期：2004.1.12

  Different arabinosides and ribosides, viz. Ara-DDA or 9(1-beta-(D)-arabinofuranosyl) 1,3-dideazaadenine (6), Ara-NDDP or 9(1-beta-D-arabinofuranosyl) 4-nitro-1,3-dideazapurine (7), Ara-DKP or I(1-beta-D-arabinofuranosyl) diketopiperazine (8), Ribo-DDA or 9(1-beta-D-ribofuranosyl) 1,3-dideazaadenine (9) and Ribo-NDDP or 9(1-beta-D-ribofuranosyl) 4-nitro-1,3-dideazapurine (10) have been synthesized as probable antiviral agents. The arabinosides have been synthesized using the catalyst TDA-1 that causes stereospecific formation of beta-nucleosides while a one-pot synthesis procedure was adopted for the synthesis of the ribonucleosides where beta-anomers were obtained in higher yields. All the five nucleoside analogs have been screened for antiviral property against HIV-1 ((IIIB)), HSV-1 and 2, parainfluenza-3, reovirus-1 and many others. It was observed that arabinosides had greater inhibitory action than ribosides. The compound 7 or Ara-NDDP has shown maximum inhibition of HIV-1 replication than the rest of the molecules with an IC50 of 79.4 mug/mL.
• KRAMAROVA, E. N.;OLENEVA, G. I.;SHIPOV, A. G.;XAUSTOVA, T. N.;ZUEVA, G. Y+, METALLORGAN. XIMIYA, 4,(1991) N, S. 468-470
  作者：KRAMAROVA, E. N.、OLENEVA, G. I.、SHIPOV, A. G.、XAUSTOVA, T. N.、ZUEVA, G. Y+

  DOI：——

  日期：——
• Shipov, A. G.; Artamkina, O. B.; Kramarova, E. P., Journal of general chemistry of the USSR, 1991, vol. 61, # 8.2, p. 1770 - 1771
  作者：Shipov, A. G.、Artamkina, O. B.、Kramarova, E. P.、Oleneva, G. I.、Baukov, Yu. I.

  DOI：——

  日期：——
• Study of Binuclear Silicon Complexes of Diketopiperazine at S_N2 Reaction Profile
  作者：Sohail Muhammad、Alan R. Bassindale、Peter G. Taylor、Louise Male、Simon J. Coles、Michael B. Hursthouse

  DOI：10.1021/om1009318

  日期：2011.2.14

  A series of binuclear pentacoordinate silicon complexes of diketopiperazine have been synthesized and substituent (leaving group) effects on the Si-O bond coordination have been studied by comparison of the five differently substituted analogous structures (X = F, Cl, OTf, Br, and I). Variable-temperature NMR spectroscopy supported by X-ray crystallography shows, for the first time in binuclear pentacoordinate silicon complexes, a complex equilibrium with both nonionic (O-Si) and ionic (Si-X) dissociation of the axial bonds in the silicon-centered trigonal bipyramids. The two dissociation pathways are consistent with a model for nucleophilic substitution in a binuclear pentacoordinate silicon compound at the silicon atom.