N,N’-bis(tert-butyldimethylsilyl)ethylenediamine | 127612-02-6

• 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: N,N’-bis(tert-butyldimethylsilyl)ethylenediamine
• 英文别名: N,N-bis(tert-butyldimethylsilyl)ethylenediamine；N,N'-Bis(dimethyl-t-butylsilyl)ethylenediamine；N,N'-bis[tert-butyl(dimethyl)silyl]ethane-1,2-diamine
• CAS: 127612-02-6
• 化学式: C₁₄H₃₆N₂Si₂
• 分子量: 288.624
• InChiKey: VXMYWEPQOOPNGE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.18
• 重原子数：
  18
• 可旋转键数：
  7
• 环数：
  0.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  24.1
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  N,N’-bis(tert-butyldimethylsilyl)ethylenediamine 在 四氯化硅 、 三乙胺 作用下， 以 乙醚 为溶剂， 反应 3.0h， 以85%的产率得到1,3-bis(tert-butyldimethylsilyl)-2,2-dichloro-1,3-diaza-2-silacyclopentane
  参考文献：
  名称：

  N,N′-Bis(silyl)ethylendiamine und 1,3-Diaza-2-silacyclopentane – Synthese, Reaktionen, Strukturen/ N,N′-Bis(silyl)ethylenediamines and 1.3-Diaza-2-silacyclopentanes – Synthesis, Reactions, Crystal Structures

  摘要：

  乙二胺与氯硅烷反应形成N,N′-双(硅基)乙二胺[(H₂CNHSiRR′R″)₂, 3: R, R′ = Me; R″ = CMe₃; 4: R = H; R′, R″= CMe₃; 5: R,R′ = CMe₃, R″ = OH]。N,N,N′-三(三甲基硅基)乙二胺与SiF₄反应得到二氟-双(1.1.4-三(三甲基硅基)乙二氨基)硅烷(6)。1.3-二氮杂-2-硅杂环戊烷R₂Si[N(SiMe₂R′)CH₂]₂, 7 - 10 (7: R = Cl, R′= Ph; 8: R = Cl, R′ = CMe₃; 9: R = H, Cl, R′ = CMe₃; 10: R = Br, R′ = CMe₃)从相应的双(硅基)乙二胺和卤硅烷在Et₂O中与NEt₃作为HHal受体反应中分离得到。N,N′-双(硅基)乙二胺的二锂衍生物与氟硅烷反应形成1.3-二氮杂-2-硅杂环戊烷，R₂Si[N(SiMe₂R′)CH₂]₂ (11 - 13) (11: R = F,R′ =Me; 12: R = F, R′ = CMe₃; 13: R = CHMe₂, R′ = Me)。N-氟-二(叔丁基硅基)-N,N′-双(三甲基硅基)-乙二胺(14)是锂化双(三甲基硅基)乙二胺与F₂Si(CMe₃)₂反应形成的产物。8在1:2的摩尔比与NaNH₂或NaOMe反应形成15和16，分别为R₂Si[N(SiMe₂CMe₃)CH₂]₂, 15: R = NH₂; 16: R = OMe。1.3-双(叔丁基二甲基硅基)-2-叔丁基二甲基硅氧基-2-氟-1.3-二氮杂-2-硅杂环戊烷是12与LiOSiMe₂CMe₃反应的产物。6和13的晶体结构已经确定。

  DOI：

  10.1515/znb-2002-0112
• 作为产物：
  描述：

  叔丁基二甲基氯硅烷 、 lithium ethylenediamide 以91%的产率得到N,N’-bis(tert-butyldimethylsilyl)ethylenediamine
  参考文献：
  名称：

  13C, 15N and 29Si nuclear magnetic resonance studies of some aminosilanes and aminodisilanes

  摘要：

  DOI：

  10.1016/0584-8539(89)80188-6

文献信息

• α-Arylation of alkylamines with sulfonylarenes through a radical chain mechanism
  作者：Yuko Ikeda、Ryota Ueno、Yuto Akai、Eiji Shirakawa

  DOI：10.1039/c8cc03604g

  日期：——

  In the presence of a substoichiometric amount of a tert-butoxy radical precursor, the reaction of alkylamines with sulfonylarenes was found to give α-arylated alkylamines through homolytic aromatic substitution, where a radical chain is operative.

  在亚化学计量量的叔丁氧基自由基前体的存在下，发现烷基胺与磺酰芳烃的反应通过均相芳族取代作用产生α-芳基化烷基胺，其中自由基链是有效的。
• Cyclic Silylhydroxylamines and 1,3-Diaza-2-Silacyclopentane – Lithium Derivatives and Reactions –
  作者：Friedhelm Diedrich、Christina Ebker、Uwe Klingebiel

  DOI：10.1080/10426500108546636

  日期：2001.1.1

  Lithium derivatives of silylhydroxylamines are used for more than thirty years. Now we are able to present the first crystal structures. Lithium is bonded side on and end on in these silylhydroxylamides. Depending on the reaction conditions and the bulkiness of the substituents dimeric, trimeric, and tetrameric oligomers are found. Fluoro-functional bis(silyl)hydroxylamines are excellent precursors

  甲硅烷基羟胺的锂衍生物使用了三十多年。现在我们能够展示第一个晶体结构。锂键合在这些甲硅烷基羟基酰胺中。根据反应条件和取代基的体积，发现二聚体、三聚体和四聚体低聚物。含氟官能的双（甲硅烷基）羟胺是环的优良前体。双（甲硅烷基）羟胺合成的副产物是 N，双（甲硅烷基）乙二胺，它们很容易环化形成 1,2-二氮杂-2-硅杂环戊烷。讨论了反应和 X 射线分析。
• 13C, 15N and 29Si nuclear magnetic resonance studies of some aminosilanes and aminodisilanes
  作者：Bernd Wrackmeyer、Carin Stader、Hong Zhou

  DOI：10.1016/0584-8539(89)80188-6

  日期：——
• N,N′-Bis(silyl)ethylendiamine und 1,3-Diaza-2-silacyclopentane – Synthese, Reaktionen, Strukturen/ N,N′-Bis(silyl)ethylenediamines and 1.3-Diaza-2-silacyclopentanes – Synthesis, Reactions, Crystal Structures
  作者：Friedhelm Diedrich、Christina Ebker、Uwe Klingebiel、Clemens Reiche、Thomas Labahn、Jörg Magull、Mathias Noltemeyer

  DOI：10.1515/znb-2002-0112

  日期：2002.1.1

  Ethylenediamine reacts with chlorosilanes to give N,N′-bis(silyl)ethylenediamines [(H₂CNHSiRR′R″)₂, 3: R, R′ = Me; R″ = CMe₃; 4: R = H; R′, R″= CMe₃; 5: R,R′ = CMe₃, R″ = OH]. In the reaction of N,N,N′-tris(trimethylsilyl)ethylenediamine with SiF₄ the difluoro-bis(1.1.4- tris(trimethylsilyl)ethylenediamino)silane (6) is obtained. The 1.3-diaza-2-silacyclopentanes R₂Si[N(SiMe₂R′)CH₂]₂, 7 - 10 (7: R = Cl, R′= Ph; 8: R = Cl, R′ = CMe₃; 9: R = H, Cl, R′ = CMe₃; 10: R = Br, R′ = CMe₃) are isolated from the reactions of the corresponding bis(silyl)ethylenediamines and halosilanes in Et₂O with NEt₃ as HHal acceptor. Dilithium derivatives of N,N′-bis(silyl)ethylenediamines react with fluorosilanes with formation of the 1.3-diaza-2-silacyclopentanes, R₂Si[N(SiMe₂R′)CH₂]₂ (11 - 13) (11: R = F,R′ =Me; 12: R = F, R′ = CMe₃; 13: R = CHMe₂, R′ = Me). N-Fluoro-di(tert-butyl)silyl-N,N′-bis(trimethylsilyl)- ethylenediamine (14) is formed in the reaction of lithiated bis(trimethylsilyl)ethylenediamine with F₂Si(CMe₃)₂. 8 reacts in amolar ratio 1:2 withNaNH₂ or NaOMe with formation of 15 and 16, respectively · R₂Si[N(SiMe₂CMe₃)CH₂]₂, 15: R = NH₂; 16: R = OMe]. 1.3-Bis(tert-butyldimethylsilyl)- 2-tert-butyldimethylsiloxy-2-fluoro-1.3-diaza-2-silacyclopentane is the product of the reaction of 12 with LiOSiMe₂CMe₃. The crystal structures of 6 and 13 have been determined.

  乙二胺与氯硅烷反应形成N,N′-双(硅基)乙二胺[(H₂CNHSiRR′R″)₂, 3: R, R′ = Me; R″ = CMe₃; 4: R = H; R′, R″= CMe₃; 5: R,R′ = CMe₃, R″ = OH]。N,N,N′-三(三甲基硅基)乙二胺与SiF₄反应得到二氟-双(1.1.4-三(三甲基硅基)乙二氨基)硅烷(6)。1.3-二氮杂-2-硅杂环戊烷R₂Si[N(SiMe₂R′)CH₂]₂, 7 - 10 (7: R = Cl, R′= Ph; 8: R = Cl, R′ = CMe₃; 9: R = H, Cl, R′ = CMe₃; 10: R = Br, R′ = CMe₃)从相应的双(硅基)乙二胺和卤硅烷在Et₂O中与NEt₃作为HHal受体反应中分离得到。N,N′-双(硅基)乙二胺的二锂衍生物与氟硅烷反应形成1.3-二氮杂-2-硅杂环戊烷，R₂Si[N(SiMe₂R′)CH₂]₂ (11 - 13) (11: R = F,R′ =Me; 12: R = F, R′ = CMe₃; 13: R = CHMe₂, R′ = Me)。N-氟-二(叔丁基硅基)-N,N′-双(三甲基硅基)-乙二胺(14)是锂化双(三甲基硅基)乙二胺与F₂Si(CMe₃)₂反应形成的产物。8在1:2的摩尔比与NaNH₂或NaOMe反应形成15和16，分别为R₂Si[N(SiMe₂CMe₃)CH₂]₂, 15: R = NH₂; 16: R = OMe。1.3-双(叔丁基二甲基硅基)-2-叔丁基二甲基硅氧基-2-氟-1.3-二氮杂-2-硅杂环戊烷是12与LiOSiMe₂CMe₃反应的产物。6和13的晶体结构已经确定。