α-Bromo O-(trimethylsilyl)butyraldoxime | 110910-96-8

• 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: α-Bromo O-(trimethylsilyl)butyraldoxime
• 英文别名: 2-bromo-N-trimethylsilyloxybutan-1-imine
• CAS: 110910-96-8
• 化学式: C₇H₁₆BrNOSi
• 分子量: 238.2
• InChiKey: MXJLBYPZJBTPKF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.0
• 重原子数：
  11.0
• 可旋转键数：
  4.0
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.86
• 拓扑面积：
  21.59
• 氢给体数：
  0.0
• 氢受体数：
  2.0

反应信息

• 作为反应物：
  描述：

  α-Bromo O-(trimethylsilyl)butyraldoxime 生成 2-Ethyl-hex-5-enal oxime
  参考文献：
  名称：

  立体合成功能化的环戊烷

  摘要：

  热分子内肟环烯烃加成物（IOOC）立体选择性地生成与异恶唑烷环稠合的5或6元碳环。这提供了有用的入口，特别是立体定向官能化的环戊烷。

  DOI：

  10.1016/s0040-4039(00)76202-2
• 作为产物：
  描述：

  O-Trimethylsilyl-n-butanaloxim 在 N-溴代丁二酰亚胺(NBS) 、 过氧化氢苯甲酰 作用下， 以 四氯化碳 为溶剂， 反应 3.5h， 生成 α-Bromo O-(trimethylsilyl)butyraldoxime
  参考文献：
  名称：

  α-Bromination of aldoximes. A route to fused azetidines.

  摘要：

  DOI：

  10.1016/s0040-4039(00)95812-x

文献信息

• Intramolecular oxime olefin cycloadditions. Stereospecific formation of functionalized pyrrolidines.
  作者：Alfred Hassner、Rakesh Maurya、Eszter Mesko

  DOI：10.1016/s0040-4039(00)80746-7

  日期：1988.1

  Allylamines possessing a properly positioned aldoxime or ketoxime chain undergo thermally induced dipolar cycloaddition to bicylic isoxazolidines, with stereospecific introduction of three stereo centers. This provides an entry into stereospecifically functionalized pyrrolidines.

  具有适当位置的醛肟或酮肟链的烯丙胺经历热诱导的偶极环加成反应形成双环异恶唑烷，并立体定向引入三个立体中心。这提供了进入立体特异性官能化的吡咯烷的入口。
• Stereochemistry. 82. Conformation of fused five-membered heterocyclic rings derived from the intramolecular oxime olefin cycloaddition reaction
  作者：Alfred Hassner、Rakesh Maurya、Oded Friedman、Hugo E. Gottlieb、Albert Padwa、David Austin

  DOI：10.1021/jo00069a011

  日期：1993.8

  Thermal intramolecular oxime olefin cycloaddition Of alpha-allylamino aldoximes and ketoximes 4 led stereospecifically to formation of oxadiazabicyclo[3.3.0]octanes 6. The presence of heteroatoms in these bicyclic fused 5-membered rings permits for the first time an evaluation of the conformation of this system by means of NMR. We found that some substituents in 6 restrict the conformational mobility of these five-membered rings to the extent that only one conformer was detected at 20-degrees-C. In other cases an equilibrium between two major conformers was revealed by NMR. Equilibrium measurements indicated a free energy of conversion of 13.2-13.4 kcal/mol, apparently a manifestation of the N-inversion in the isoxazolidine ring. NMR studies also showed that the NH-proton in isoxazolidines 6 prefers an axial orientation. Empirical force field data were adjusted for MM calculations in these bicyclic heterocycles. The MM2 force field with AMBER charge gave the best fit between calculated and experimental coupling constants.