2-(trimethylsilyl)-2-azacyclooctanone | 57012-52-9

• 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: 2-(trimethylsilyl)-2-azacyclooctanone
• 英文别名: N-SiMe3-enantolactam；1-Trimethylsilylazocan-2-one
• CAS: 57012-52-9
• 化学式: C₁₀H₂₁NOSi
• 分子量: 199.368
• InChiKey: ZUJBAENYQIIMJX-UHFFFAOYSA-N

物化性质

• 沸点：
  87 °C(Press: 2.5 Torr)
• 密度：
  0.92±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.61
• 重原子数：
  13
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.9
• 拓扑面积：
  20.3
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  2-(trimethylsilyl)-2-azacyclooctanone 在 水 、 碳酸氢铵 作用下， 以 正己烷 、 二氯甲烷 为溶剂， 反应 120.0h， 生成 1,1,3,3-tetramethyl-1,3-bis[(2-oxoazocan-1-yl)methyl]disiloxane
  参考文献：
  名称：

  Scheme of hydrolysis of five-coordinate chlorosilanes by X-ray diffraction data

  摘要：

  Hydrolysis of monochelate five-coordinate chlorosilanes MeC(O)N(Me)CH2SiMe2Cl (Ia), (LCH2SiMe2Cl)-C-7 (Ib), (LCH2SiMe2Cl)-C-8 (Ic), PhtImCH(2)SiMe(2)Cl (Id), MeC(O)N(Me)CH2SiMePhCl (IIa), and Im(5)CH(2)SiMePhCl (IIe), containing a monoanionic C,O-chelating ligand LCH2 [L is an amide, n-membered lactam (L (n) ), imide (Im (n) ), or phthalimide (PhtIm) residue]. The structures of the starting chlorides and their hydrolysis products were established by means of X-ray diffraction analysis. Based on experimental and published data, a general scheme of hydrolysis of mono-C,O-chelate chlorosilanes was suggested, including initial formation of silyloxonium chlorides III and subsequent formation of disiloxane dihydrochlorides IV.

  DOI：

  10.1134/s1070363211120048
• 作为产物：
  描述：

  氮杂环辛酮 、 三甲基氯硅烷 在 三乙胺 作用下， 以 甲苯 为溶剂， 以95%的产率得到2-(trimethylsilyl)-2-azacyclooctanone
  参考文献：
  名称：

  Selective nucleophilic addition reactions of alkyllithium reagents with N-(trimethylsilyl)lactams. Synthesis of cyclic ketimines

  摘要：

  DOI：

  10.1021/jo00298a062

文献信息

• Donor-stabilized germylium cations. To the scheme of formation of bis(chelate) germylium ions using the complexes with lactamomethyl (С,О)-chelate ligand (enantolactam derivatives) as an example
  作者：A. A. Korlyukov、E. A. Komissarov、E. P. Kramarova、A. G. Shipov、Vad. V. Negrebetsky、S. Yu. Bylikin、Yu. I. Baukov

  DOI：10.1007/s11172-016-1622-6

  日期：2016.11

  dichlorogermane 1 into the bis(chelate) cationic complex (L8CH2)2Ge(Cl)OTf (2) was proposed. The H-bonded complexes of dichlorogermane 1 with HOSO2CF3 and HCl assumed to be intermediates in this process were studied by quantum chemical calculation. The energy necessary for the dissociation of the H-bonded complexes to the germylium cation and HCl2– and СlHOSO2CF3– anions depends on the relative arrangement

  合成了双(螯合)二氯锗烷(L8CH2)2GeCl2(1)和基于烯内酰胺(L8H)的单阴离子内酰胺甲基(С,О)-螯合配体，并研究了其分子和晶体结构。锗原子的特征是八面体构型，Cl和O原子相互顺式排列，C原子反式排列。提出了将二氯锗烷 1 转化为双（螯合）阳离子络合物 (L8CH2)2Ge(Cl)OTf (2) 的方案。二氯锗烷 1 与 HOSO2CF3 和 HCl 的 H 键配合物被假定为该过程中的中间体，通过量子化学计算进行了研究。氢键配合物解离为锗阳离子和 HCl2– 和 СlHOSO2CF3– 阴离子所需的能量取决于 Cl 原子在 Ge 原子配位多面体中的相对排列。在 H 键配合物中 Cl 原子顺式排列的情况下，解离能估计为 11.5-16.1 kcal mol-1。
• HUA, DUY H.;MIAO, SHOU WU;BHARATHI, S. NARASIMHA;KATSUHIRA, TAKESHI;BRAVO+, J. ORG. CHEM., 55,(1990) N1, C. 3682-3684
  作者：HUA, DUY H.、MIAO, SHOU WU、BHARATHI, S. NARASIMHA、KATSUHIRA, TAKESHI、BRAVO+

  DOI：——

  日期：——
• Selective nucleophilic addition reactions of alkyllithium reagents with N-(trimethylsilyl)lactams. Synthesis of cyclic ketimines
  作者：Duy H. Hua、Shou Wu Miao、S. Narasimha Bharathi、Takeshi Katsuhira、Ana A. Bravo

  DOI：10.1021/jo00298a062

  日期：1990.5
• Scheme of hydrolysis of five-coordinate chlorosilanes by X-ray diffraction data
  作者：A. G. Shipov、E. P. Kramarova、T. P. Murasheva、A. A. Korlyukov、S. A. Pogozhikh、S. A. Tarasenko、V. V. Negrebetskii、I. P. Yakovlev、Yu. I. Baukov

  DOI：10.1134/s1070363211120048

  日期：2011.12

  Hydrolysis of monochelate five-coordinate chlorosilanes MeC(O)N(Me)CH2SiMe2Cl (Ia), (LCH2SiMe2Cl)-C-7 (Ib), (LCH2SiMe2Cl)-C-8 (Ic), PhtImCH(2)SiMe(2)Cl (Id), MeC(O)N(Me)CH2SiMePhCl (IIa), and Im(5)CH(2)SiMePhCl (IIe), containing a monoanionic C,O-chelating ligand LCH2 [L is an amide, n-membered lactam (L (n) ), imide (Im (n) ), or phthalimide (PhtIm) residue]. The structures of the starting chlorides and their hydrolysis products were established by means of X-ray diffraction analysis. Based on experimental and published data, a general scheme of hydrolysis of mono-C,O-chelate chlorosilanes was suggested, including initial formation of silyloxonium chlorides III and subsequent formation of disiloxane dihydrochlorides IV.