N,N-dimethylamide O-SiMe3-(S)-lactic acid | 1262286-31-6

• 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-dimethylamide O-SiMe3-(S)-lactic acid
• 英文别名: (2S)-N,N-dimethyl-2-trimethylsilyloxypropanamide
• CAS: 1262286-31-6
• 化学式: C₈H₁₉NO₂Si
• 分子量: 189.33
• InChiKey: IUXNXBKTGPDCLZ-ZETCQYMHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.31
• 重原子数：
  12
• 可旋转键数：
  3
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.88
• 拓扑面积：
  29.5
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  N,N-dimethylamide O-SiMe3-(S)-lactic acid 在 四氯化硅 作用下， 以 正己烷 为溶剂， 以81%的产率得到bis[1-(dimethylcarbamoyl)ethoxy]chlorosilylium chloride
  参考文献：
  名称：

  Donor-stabilized five-coordinate cationic chelate silicon compounds with two (O→Si)-coordinating ligands

  摘要：

  Cationic O -> Si-coordinated bis-C,O-chelate silicon complexes [(LCH2)(2)Si(F)]BF4, containing monoanionic AcN(Me)CH2, 2-oxoperhydroazepinomethyl, 2,2-dimethyl-4-oxobenzo[1,3]oxazin-3-ylmethyl, and 4-methyl-2-oxoquinolinomethyl C,O-coordinating ligands were synthesized by the reaction of trimethylsilyl derivatives of amides, lactams, and related compounds with (ClCH2)(2)SiCl2 in a 2:1 ratio. The synthesized complexes were reacted with KF to obtain six-coordinate bis-C,O-chelates [(LCH2)(2)SiF2] which were then converted into the starting tetrafluoroborates by treatment with BF3 center dot Et2O. First representatives of cationic bis-O,O'-chelate silicon complexes with a 2-hydroxyacid amide fragment {XSi[OCH(R)C(O)NMe2](2)}Y (X = Cl, Me, t-Bu, Ph, BrCH2; R = H, Me; Y - Cl-, ClHCl-, HgBr (3) (-) ) were synthesized by the reaction of XSiCl3 with O -> SiMe3 derivatives of dimethylamides of (S)-lactic and glycolic acids in a 1:2 ratio or by transesterification of XSi(OMe)(3) with glycolic acid dimethylamide followed by addition of acetyl bromide (ratio 1:3:1). The structure of the resulting chelates was proved by X-ray diffraction analysis.

  DOI：

  10.1134/s1070363211120036
• 作为产物：
  描述：

  三甲基氯硅烷 、 (2S)-2-羟基-N,N-二甲基丙酰胺 在 六甲基二硅氮烷 作用下， 生成 N,N-dimethylamide O-SiMe3-(S)-lactic acid
  参考文献：
  名称：

  衍生自 2-羟基羧酸的 N,N-二取代酰胺的三氯和甲基二氯锗烷基单螯合物以及二溴和二氯锗烷基双螯合物

  摘要：

  GeCl4、GeBr4 和 MeGeCl3 与 2-羟基羧酸的 N,N-二取代酰胺的 O-三甲基甲硅烷基衍生物反应得到五配位和六配位中性 (O,O)-单-和 (O,O)-双螯合物。乙醇酸衍生物与 GeX4 反应生成双螯合物 X2Ge[OCH2C(O)NR2R3]27a,c,d (X = Cl, R2 = R3 = Me (a), (CH2)5 (c), (CH2CH2)2O ( d)) 和 8a (X = Br)。相比之下，乳酸和扁桃酸衍生物与 GeCl4 和 MeGeCl3 的反应得到单螯合物 Cl3Ge[OCH(R1)C(O)NR2R3] (S)-9a–c (R1 = Me) 和 Cl2MeGe[OCH(R1)C( O)NR2R3] 10a (R1 = H)、(S)-11a,b (R1 = Me) 和 (S)-12a (R1 = Ph) (R2R3 = (CH2)4 (b))。根据 X

  DOI：

  10.1007/s11172-012-0093-7

文献信息

• Trichloro- and methyldichlorogermyl monochelates and dibromo- and dichlorogermyl bischelates derived from N,N-disubstituted amides of 2-hydroxycarboxylic acids
  作者：D. V. Airapetyan、T. P. Murasheva、S. Yu. Bylikin、A. A. Korlyukov、A. G. Shipov、S. V. Gruener、E. P. Kramarova、Vad. V. Negrebetskii、S. A. Pogozhikh、G. Ya. Zueva、M. Yu. Antipin、Yu. I. Baukov

  DOI：10.1007/s11172-012-0093-7

  日期：2012.3

  The reactions of GeCl4, GeBr4, and MeGeCl3 with O-trimethylsilyl derivatives of N,N-disubstituted amides of 2-hydroxycarboxylic acids afforded pentacoordinate and hexacoordinate neutral (O,O)-mono- and (O,O)-bischelates. The reactions of glycolic acid derivatives with GeX4 produced bischelates X2Ge[OCH2C(O)NR2R3]27a,c,d (X = Cl, R2 = R3 = Me (a), (CH2)5 (c), (CH2CH2)2O (d)) and 8a (X = Br). By contrast

  GeCl4、GeBr4 和 MeGeCl3 与 2-羟基羧酸的 N,N-二取代酰胺的 O-三甲基甲硅烷基衍生物反应得到五配位和六配位中性 (O,O)-单-和 (O,O)-双螯合物。乙醇酸衍生物与 GeX4 反应生成双螯合物 X2Ge[OCH2C(O)NR2R3]27a,c,d (X = Cl, R2 = R3 = Me (a), (CH2)5 (c), (CH2CH2)2O ( d)) 和 8a (X = Br)。相比之下，乳酸和扁桃酸衍生物与 GeCl4 和 MeGeCl3 的反应得到单螯合物 Cl3Ge[OCH(R1)C(O)NR2R3] (S)-9a–c (R1 = Me) 和 Cl2MeGe[OCH(R1)C( O)NR2R3] 10a (R1 = H)、(S)-11a,b (R1 = Me) 和 (S)-12a (R1 = Ph) (R2R3 = (CH2)4 (b))。根据 X
• Donor-stabilized five-coordinate cationic chelate silicon compounds with two (O→Si)-coordinating ligands
  作者：A. G. Shipov、A. A. Korlyukov、E. P. Kramarova、D. E. Arkhipov、S. Yu. Bylikin、Fan Hunze、S. A. Pogozhikh、T. P. Murasheva、V. V. Negrebetskii、V. N. Khrustalev、Yu. E. Ovchinnikov、A. R. Bassindale、P. G. A. Taylor、Yu. I. Baukov

  DOI：10.1134/s1070363211120036

  日期：2011.12

  Cationic O -> Si-coordinated bis-C,O-chelate silicon complexes [(LCH2)(2)Si(F)]BF4, containing monoanionic AcN(Me)CH2, 2-oxoperhydroazepinomethyl, 2,2-dimethyl-4-oxobenzo[1,3]oxazin-3-ylmethyl, and 4-methyl-2-oxoquinolinomethyl C,O-coordinating ligands were synthesized by the reaction of trimethylsilyl derivatives of amides, lactams, and related compounds with (ClCH2)(2)SiCl2 in a 2:1 ratio. The synthesized complexes were reacted with KF to obtain six-coordinate bis-C,O-chelates [(LCH2)(2)SiF2] which were then converted into the starting tetrafluoroborates by treatment with BF3 center dot Et2O. First representatives of cationic bis-O,O'-chelate silicon complexes with a 2-hydroxyacid amide fragment XSi[OCH(R)C(O)NMe2](2)}Y (X = Cl, Me, t-Bu, Ph, BrCH2; R = H, Me; Y - Cl-, ClHCl-, HgBr (3) (-) ) were synthesized by the reaction of XSiCl3 with O -> SiMe3 derivatives of dimethylamides of (S)-lactic and glycolic acids in a 1:2 ratio or by transesterification of XSi(OMe)(3) with glycolic acid dimethylamide followed by addition of acetyl bromide (ratio 1:3:1). The structure of the resulting chelates was proved by X-ray diffraction analysis.