1,3-bis<2-(diethylamino)ethyl>tetramethyldisiloxane | 42078-16-0

• 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: 1,3-bis<2-(diethylamino)ethyl>tetramethyldisiloxane
• 英文别名: 1,1,3,3-tetramethyl-1,3-bis<2-(diethylamino)ethyl>disiloxane；2-[[2-(diethylamino)ethyl-dimethylsilyl]oxy-dimethylsilyl]-N,N-diethylethanamine
• CAS: 42078-16-0
• 化学式: C₁₆H₄₀N₂OSi₂
• 分子量: 332.677
• InChiKey: YCSRCDLCYSDYOL-UHFFFAOYSA-N

物化性质

• 沸点：
  114-116 °C(Press: 2 Torr)
• 密度：
  0.8630 g/cm3

计算性质

• 辛醇/水分配系数(LogP)：
  4.1
• 重原子数：
  21
• 可旋转键数：
  12
• 环数：
  0.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  15.7
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  2-[diethylamino(dimethyl)silyl]-N,N-diethylethanamine 在 盐酸 作用下， 反应 3.0h， 以40%的产率得到1,3-bis<2-(diethylamino)ethyl>tetramethyldisiloxane
  参考文献：
  名称：

  Perchenko, V. N.; Kamneva, G. L.; Nametkin, N. S., Journal of general chemistry of the USSR, 1982, vol. 52, # 2, p. 313 - 320

  摘要：

  DOI：

文献信息

• Reactivity of Lithium Alkylamide toward Vinylsilane Derivatives
  作者：Yukio Nagasaki、Shinya Morishita、Masao Kato、Yasuharu Kihara、Teiji Tsuruta

  DOI：10.1246/bcsj.65.949

  日期：1992.4

  Kinetic studies concerning the addition reactions of lithium diethylamide (Et2NLi) to several vinylsilane derivatives, such as H2C=CH–Si(CH3)2X [X: methyl, phenyl, ethoxy, 2-(diethylamino)ethyl and vinyl], and H2C=CH–Si(CH3)2OSi(CH3)2X [X: 2-(diethylamino)ethyl and vinyl], were carried out. The reactivity of vinylsilane derivatives toward nucleophile was strongly influenced by the nature of the substituents on the Si atom. The reactivity of trimethylvinylsilane [rate constant k (trimethylvinylsilane; cHx; 50 °C) = 2.9 ± 0.2 · 10−4 dm3 mol−1 s−1] was found to be of the same order of magnitude as that of para-alkyl-substituted styrenes, such as 4-methylstyrene [k (4-methylstyrene; cHx; 50 °C) = 3.2 · 10−4 dm3 mol−1 s−1]. The reactivities of vinylsilane compounds having an aryl substituent, e.g. dimethylphenylvinylsilane [k (dimethylphenylvinylsilane; cHx; 50 °C) = 14.8 ± 0.3 · 10−4 dm3 mol−1 s−1] and dimethyldivinylsilane [k (dimethyldivinylsilane; cHx; 50 °C) = 14.8 ± 0.6 · 10−4 dm3 mol−1 s−1], were higher than that of trialkyl-substituted vinylsilane. This fact may be explained by a π-conjugation between the phenyl (or vinyl) and vinyl groups through an empty d-orbital of the Si atom. A vinylsilane compound having a 2-(dialkylamino)ethyl substituent, [2-(diethylamino)ethyl]dimethylvinylsilane, showed unique reactivity toward lithium diethylamide, indicating that the β-nitrogen atom plays an important role regarding the reactivity of the vinyl group. In the reaction between lithium diethylamide and vinylsilane having an ethoxyl group, an addition reaction to the vinyl group and a cleavage reaction of the Si–O linkage proceeded concurrently. No cleavage reaction, however, proceeded in the reaction of lithium diethylamide with vinylsilane compounds having a disiloxane linkage. 1,1,3,3-Tetramethyl-1,3-divinyldisiloxane exhibited a much higher reactivity than did the other vinylsilane compounds.

  对二乙基酰胺锂（Et2NLi）与几种乙烯基硅烷衍生物（如 H2C=CH-Si(CH3)2X [X：甲基、苯基、乙氧基、2-(二乙基氨基)乙基和乙烯基]，以及 H2C=CH-Si( )2OSi( )2X [X：2-(二乙基氨基)乙基和乙烯基]）的加成反应进行了动力学研究。乙烯基硅烷衍生物对亲核物的反应性受到硅原子上取代基性质的强烈影响。研究发现，三甲基乙烯基硅烷的反应活性[速率常数 k（三甲基乙烯基硅烷；cHx；50 °C）= 2.9 ± 0.2 - 10-4 dm3 mol-1 s-1]与对烷基取代的苯乙烯（如 4-甲基苯乙烯）的反应活性[k（4-甲基苯乙烯；cHx；50 °C）= 3.2 - 10-4 dm3 mol-1 s-1]处于同一数量级。具有芳基取代基的乙烯基硅烷化合物的反应活性，例如二甲基苯基乙烯基硅烷 [k (dimethylphenylvinylsilane; cHx; 50 °C) = 14.8 ± 0.3 - 10-4 dm3 mol-1 s-1] 和二甲基二乙烯基硅烷 [k (dimethyldivinylsilane; cHx; 50 °C) = 14.8 ± 0.6 - 10-4 dm3 mol-1 s-1] 均高于三烷基取代的乙烯基硅烷。这可能是因为苯基（或乙烯基）和乙烯基通过 Si 原子的空 d 轨道发生了 π 共轭作用。具有 2-（二烷基氨基）乙基取代基的乙烯基硅烷化合物--[2-（二乙基氨基）乙基]二甲基乙烯基硅烷对二乙基酰胺锂显示出独特的反应活性，这表明β-氮原子对乙烯基的反应活性起着重要作用。在二乙基酰胺锂和带有乙氧基的乙烯基硅烷的反应中，乙烯基的加成反应和 Si-O 连接的裂解反应同时进行。然而，在二乙基酰胺锂与具有二硅氧烷连接的乙烯基硅烷化合物的反应中，没有发生裂解反应。1,1,3,3-四甲基-1,3-二乙烯基二硅氧烷的反应活性远远高于其他乙烯基硅烷化合物。
• Some transformations of secondary and tertiary triorgano-?-aminoethylsilanes
  作者：N. S. Nametkin、V. N. Perchenko、I. A. Grushevenko、G. L. Kamneva、T. I. Derenkovskaya、M. �. Kuzovkina

  DOI：10.1007/bf00857064

  日期：1973.4