Piperidine-1-carboxylic acid 2-trimethylsilanyl-ethyl ester | 113237-06-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 哌啶类
• 英文名称: Piperidine-1-carboxylic acid 2-trimethylsilanyl-ethyl ester
• 英文别名: 2-Trimethylsilylethyl piperidine-1-carboxylate
• CAS: 113237-06-2
• 化学式: C₁₁H₂₃NO₂Si
• 分子量: 229.395
• InChiKey: GVMNJOMTQUDVRM-UHFFFAOYSA-N

物化性质

• 沸点：
  283.8±23.0 °C(Predicted)
• 密度：
  0.968±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.95
• 重原子数：
  15
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.91
• 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：

  Piperidine-1-carboxylic acid 2-trimethylsilanyl-ethyl ester 在 四丁基氟化铵 作用下， 以98%的产率得到哌啶
  参考文献：
  名称：

  The mild and selective N-debenzylation of tertiary alkylamines using β-trimethylsilylethyl chloroformate.

  摘要：

  DOI：

  10.1016/s0040-4039(00)96116-1
• 作为产物：
  描述：

  2-(三甲硅基)乙醇 在 三乙胺 作用下， 以 乙醚 、 甲苯 为溶剂， 反应 2.0h， 生成 Piperidine-1-carboxylic acid 2-trimethylsilanyl-ethyl ester
  参考文献：
  名称：

  Resolved pyrrolidine, piperidine, and perhydroazepine analogs of the muscarinic agent N-methyl-N-(1-methyl-4-pyrrolidino-2-butynyl)acetamide

  摘要：

  A series of conformationally restricted analogues of the partial muscarinic agonist N-methyl-N-(1-methyl-4-pyrrolidino-2-butynyl)acetamide (BM 5; 1) was synthesized. Three of the racemic derivatives were resolved into the enantiomers. The compounds were investigated for muscarinic and antimuscarinic activity in the isolated guinea pig ileum. They were found to be fairly potent muscarinic antagonists or weak partial agonists. The new compounds were either equally or less potent than 1 in inhibiting (-)-[3H]-N-methylscopolamine binding in homogenates of the rat cerebral cortex. Thus, structural modifications to 1 in which the amide moiety and the methyl group in the butynyl chain have been joined to form a six- or seven-membered ring preserve affinity but abolish efficacy. The R enantiomers were found to have 14-79 times higher affinity to ileal muscarinic receptors than the respective antipodes. The enantiomeric affinity ratios were nearly identical in both preparations studied. As suggested by molecular mechanics calculations, the difference in affinity between the five-membered and the six- and seven-membered ring analogues may be rationalized in conformational terms.

  DOI：

  10.1021/jm00174a014

文献信息

• Facile synthesis of resolved α-ethynyl-substituted cyclic amines
  作者：J.R Michael Lundkvist、Lars-G Wistrand、Uli Hacksella

  DOI：10.1016/s0040-4039(00)94612-4

  日期：1990.1

  A series of resolved α-acetylenic pyrrolidinyl, piperidinyl and perhydroazepinyl derivatives has been synthesized by a facile route including a key anodic oxidation step. Assignments of absolute configurations were based on chemical correlation and circular dichroism spectroscopy.

  已经通过包括关键阳极氧化步骤在内的简便方法合成了一系列拆分的α-炔基吡咯烷基，哌啶基和全氢a庚啶基衍生物。绝对构型的分配基于化学相关性和圆二色性光谱。
• Improved synthesis of quinine alkaloids with the Teoc protective group
  作者：Junji Igarashi、Yuichi Kobayashi

  DOI：10.1016/j.tetlet.2005.06.171

  日期：2005.9

  TeocCl (Teoc: C(=O)O(CH2)(2)TMS) generated in situ was conveniently used for trans-protection of the N-Bn piperidine intermediate to N-Teoc piperidine. Later, deprotection of the Teoc group and the subsequent quinuclidine ring formation was achieved with CsF in a domino fashion to afford the quinine alkaloids. (c) 2005 Elsevier Ltd. All rights reserved.
• LUNDKVIST, J. R. M.;WISTRAND, L. -G.;HACKSELL, U., TETRAHEDRON LETT., 31,(1990) N, C. 719-722
  作者：LUNDKVIST, J. R. M.、WISTRAND, L. -G.、HACKSELL, U.

  DOI：——

  日期：——
• LUNDKVIST, J. R. MICHAEL;VARGAS, HUGO M.;CALDIROLA, PATRIZIA;RINGDAHL, BJ+, J. MED. CHEM., 33,(1990) N2, C. 3182-3189
  作者：LUNDKVIST, J. R. MICHAEL、VARGAS, HUGO M.、CALDIROLA, PATRIZIA、RINGDAHL, BJ+

  DOI：——

  日期：——
• CAMPBELL, ARTHUR L.;PILIPAUSKAS, DANIEL R.;KHANNA, ISH K.;RHODES, R. ALLE+, TETRAHEDRON LETT., 28,(1987) N 21, 2331-2334
  作者：CAMPBELL, ARTHUR L.、PILIPAUSKAS, DANIEL R.、KHANNA, ISH K.、RHODES, R. ALLE+

  DOI：——

  日期：——