(2S)-2-[(tert-butyl)dimethylsilyloxy]-N-(trimethylsilyl)propan-1-imine | 116102-34-2

• 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: (2S)-2-[(tert-butyl)dimethylsilyloxy]-N-(trimethylsilyl)propan-1-imine
• 英文别名: (2S)-2-[tert-butyl(dimethyl)silyl]oxy-N-trimethylsilylpropan-1-imine
• CAS: 116102-34-2
• 化学式: C₁₂H₂₉NOSi₂
• 分子量: 259.539
• InChiKey: IHDJKGQRNZTCAN-NSHDSACASA-N

物化性质

• 沸点：
  254.9±42.0 °C(Predicted)
• 密度：
  0.82±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.3
• 重原子数：
  16
• 可旋转键数：
  5
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.92
• 拓扑面积：
  21.6
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (2S)-2-[(tert-butyl)dimethylsilyloxy]-N-(trimethylsilyl)propan-1-imine 在 三乙胺 作用下， 以 正己烷 、 正庚烷 、 甲苯 为溶剂， 生成 (3R,4R)-3-bromo-4-[(1S)-1-tert-butyldimethylsilyloxy]ethyl-azetidin-2-one
  参考文献：
  名称：

  A Trans-Stereoselective Synthesis of 3-Halo-4-alkyl(aryl)-NH-azetidin-2-ones

  摘要：

  Conrotatory ring closure of 1-halo-3-aza-4-alkyl-1,3-dienes in refluxing toluene gives rise to 3-halo-4-aryl-2-azetidinones in satisfactory yields. Dehalogenation of the resulting beta-lactams by tris(trimethylsilyl)silane furnished 3-unsubstituted azetidinones, valuable intermediates in the synthesis of biologically active compounds.

  DOI：

  10.1021/ol005633x
• 作为产物：
  描述：

  (S)-2-(叔丁基-二甲基-锡氧基)-丙醛 、 lithium hexamethyldisilazane 以 四氢呋喃 为溶剂， 反应 1.0h， 生成 (2S)-2-[(tert-butyl)dimethylsilyloxy]-N-(trimethylsilyl)propan-1-imine
  参考文献：
  名称：

  N-金属亚胺：从醛制取α-氨基醇的新方法。

  摘要：

  将烷基锂或格氏试剂添加到原位产生的O-保护的α-羟基-N-三甲基甲硅烷基亚胺中，以良好的收率和高度立体控制的方式进行以产生1,2-氨基。

  DOI：

  10.1016/0040-4039(91)80664-r

文献信息

• N-metallo imines: A new approach to α-amino alcohols from aldehydes.
  作者：Gianfranco Cainelli、Daria Giacomini、Elisabetta Mezzina、Mauro Panunzio、Paola Zarantonello

  DOI：10.1016/0040-4039(91)80664-r

  日期：1991.6

  The addition of lithium alkyls or Grignard reagents to the in situ generated O-protected α-hydroxy-N- trimethylsilylimines proceeds in good yields and highly stereocontrolled manner to produce 1,2 -aminols.

  将烷基锂或格氏试剂添加到原位产生的O-保护的α-羟基-N-三甲基甲硅烷基亚胺中，以良好的收率和高度立体控制的方式进行以产生1,2-氨基。
• Acyclic stereocontrol in the addition of trimethylsilyl cyanide to N-substituted imines of (2S)-lactic aldehyde
  作者：Gianfranco Cainelli、Daria Giacomini、Alessandra Treré、Paola Galletti

  DOI：10.1016/0957-4166(95)00203-2

  日期：1995.7

  The cyanosilylation of a series of N-substituted lactaldehyde imines is reported. The trimethylsilylcyanide addition affords optically active α-amino nitriles. All the imines show a syn diastereofacial selectivity that is maintained irrespective to the nature of the Lewis acid employed and even remains in the noncatalyzed reaction.

  报道了一系列N-取代的乳醛亚胺的氰基硅烷化。三甲基甲硅烷基氰化物的加成得到旋光的α-氨基腈。所有亚胺都显示出同构的非对映选择性，而与所用路易斯酸的性质无关，甚至可以保留在非催化反应中。
• Butyllithium Addition toα-Chiral Compounds: Solvent Mixture Effects on Diastereofacial Selectivity
  作者：Gianfranco Cainelli、Paola Galletti、Daria Giacomini、Paolo Orioli、Mario A. Polidoro、Maria Cristina Righetti

  DOI：10.1002/1522-2675(20000809)83:8<1951::aid-hlca1951>3.0.co;2-g

  日期：2000.8.9

  Temperature-dependent selectivity in nucleophilic additions is affected by the solvent. In this context, we investigated the effect on diastereoselectivity of solvent mixtures with respect to pure solvents. Binary systems of THF/hexane and of four different hydrocarbon mixtures were employed in BuLi addition to 2-phenylpropanal, (2S)-2-[(tert-butyl)dimethylsilyloxy]-2-phenylethanal, and (2S)-2-[(tert-butyl)dimethylsilyloxyl]-N-(trimethylsilyl)propan-1-imine. A 5-mol-% of THF in hexane affects the isomer ratio by reducing both Delta Delta H-not equal and Delta Delta S not equal contributions, and suppresses T-inv. On the contrary, in hydrocarbon binary mixtures, the T-inv is still observed and occurs at a higher temperature than in pure solvents. Studying the dependence of T-inv on the hexane/decane mixture composition, we propose the formation of a peculiar solvation cluster that is unaffected by the composition of the bulk reaction solvent.
• 10.1002/1099-0690(200209)2002:18<3153::aid-ejoc3153<3.0.co;2-d
  作者：Cainelli, Gianfranco、Giacomini, Daria、Galletti, Paola、Quintavalla, Arianna

  DOI：10.1002/1099-0690(200209)2002:18<3153::aid-ejoc3153<3.0.co;2-d

  日期：——
• A Trans-Stereoselective Synthesis of 3-Halo-4-alkyl(aryl)-NH-azetidin-2-ones
  作者：Elisa Bandini、Gianfranco Favi、Giorgio Martelli、Mauro Panunzio、Giovanni Piersanti

  DOI：10.1021/ol005633x

  日期：2000.4.1

  Conrotatory ring closure of 1-halo-3-aza-4-alkyl-1,3-dienes in refluxing toluene gives rise to 3-halo-4-aryl-2-azetidinones in satisfactory yields. Dehalogenation of the resulting beta-lactams by tris(trimethylsilyl)silane furnished 3-unsubstituted azetidinones, valuable intermediates in the synthesis of biologically active compounds.