trimethylsilyl (S)-piperidine-2-carboxylate | 1193378-35-6

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: trimethylsilyl (S)-piperidine-2-carboxylate
• 英文别名: trimethylsilyl (2S)-piperidine-2-carboxylate
• CAS: 1193378-35-6
• 化学式: C₉H₁₉NO₂Si
• 分子量: 201.341
• InChiKey: FPPDHYMXBHTGOC-QMMMGPOBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.51
• 重原子数：
  13
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.89
• 拓扑面积：
  38.3
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  ethyl 8-oxooct-4-en-2-ynoate 、 trimethylsilyl (S)-piperidine-2-carboxylate 以 甲苯 为溶剂， 反应 1.0h， 以78%的产率得到ethyl 3,4,4a,6,7,8,9,9a-octahydropyrido[1,2-a]indole-10-carboxylate
  参考文献：
  名称：

  An Efficient Synthetic Approach to Polycyclic 2,5-Dihydropyrroles from α-Silyloxy Ketones

  摘要：

  A three-step sequence to prepare polycyclic 2,5-dihydropyrroles from alpha-silyloxy ketones is presented. A Lewis acid-mediated ring fragmentation of cyclic gamma-sjlyloxy-beta-hydroxy-alpha-diazo esters provided tethered aldehyde ynoate intermediates which, when treated with amino acid silyl esters, underwent intramolecular azomethine ylide 1,3-dipolar cycloadditions. The 2,5-dihydropyrrole products were formed in good to excellent yield as single diastereomers.

  DOI：

  10.1021/jo901978y

文献信息

• [3 + 2]-Dipolar Cycloaddition of Aldehyde-Tethered Alkynamides and Trimethylsilyl Amino Esters: A Gateway to Uniquely Functionalized Polycyclic N-Heterocycles via Post-Ugi Functionalization
  作者：Anirban Ghoshal、Anamika Yadav、Ajay Kumar Srivastava

  DOI：10.1021/acs.joc.0c01539

  日期：2020.12.4

  pyrrolo-pyrrolizinones, pyrido-pyrrolizinones, and azepino-pyrrolizinones via [3 + 2]-dipolar cycloaddition is described. The method involves the synthesis of tethered alkynamides using Ugi condensation and oxidation that were subsequently subjected to a dipolar cycloaddition reaction with trimethylsilyl amino esters. Further transformations to demonstrate the utility of these scaffolds were also investigated

  描述了一种通过[3 + 2]-偶极环加成生成独特官能化的吡咯并吡咯并酮，吡啶并吡咯并酮和氮杂吡咯并酮的有效方法。该方法包括使用Ugi缩合和氧化合成束缚的炔酰胺，其随后与三甲基甲硅烷基氨基酯进行偶极环加成反应。还研究了进一步的转化以证明这些支架的效用。