2-methoxy-1-<<2-(trimethylsilyl)ethoxy>carbonyl>perhydroazepine | 128980-86-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 氮杂环庚烷
• 英文名称: 2-methoxy-1-<<2-(trimethylsilyl)ethoxy>carbonyl>perhydroazepine
• 英文别名: 2-(trimethylsilyl)ethyl 2-methoxyazepane-1-carboxylate；2-trimethylsilylethyl 2-methoxyazepane-1-carboxylate
• CAS: 128980-86-9
• 化学式: C₁₃H₂₇NO₃Si
• 分子量: 273.448
• InChiKey: VDVRCRHXIQXOLX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.31
• 重原子数：
  18.0
• 可旋转键数：
  4.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.92
• 拓扑面积：
  38.77
• 氢给体数：
  0.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  2-methoxy-1-<<2-(trimethylsilyl)ethoxy>carbonyl>perhydroazepine 、 二(三甲基甲硅烷基)乙炔 在 三氯化铝 作用下， 生成 (+/-)-2-<2-(trimethylsilyl)ethynyl>perhydroazepine
  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
• 作为产物：
  描述：

  2-(三甲硅基)乙醇 在 tetrabutylammonium tetrafluoroborate 、 三乙胺 作用下， 以 乙醚 、 甲苯 为溶剂， 反应 2.0h， 生成 2-methoxy-1-<<2-(trimethylsilyl)ethoxy>carbonyl>perhydroazepine
  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

• Expedient Preparation of Nazlinine and a Small Library of Indole Alkaloids Using Flow Electrochemistry as an Enabling Technology
  作者：Mikhail A. Kabeshov、Biagia Musio、Philip R. D. Murray、Duncan L. Browne、Steven V. Ley

  DOI：10.1021/ol502201d

  日期：2014.9.5

  An expedient synthesis of the indole alkaloid nazlinine is reported. Judicious choice of flow electrochemistry as an enabling technology has permitted the rapid generation of a small library of unnatural relatives of this biologically active molecule. Furthermore, by conducting the key electrochemical Shono oxidation in a flow cell, the loading of electrolyte can be significantly reduced to 20 mol

  据报道，吲哚生物碱纳兹林碱的简便合成方法。明智地选择流动电化学作为一种使能技术，可以快速生成这种生物活性分子的非天然亲戚的小型文库。此外，通过在流通池中进行关键的电化学Shono氧化，可以将电解质的负载显着降低至20 mol％，同时保持稳定，广泛适用的过程。
• 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。
• 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：——