(3-Piperidiniopropyl)magnesiumchlorid | 34924-24-8

• 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: (3-Piperidiniopropyl)magnesiumchlorid
• 英文别名: 3-piperidinopropyl magnesium chloride
• CAS: 34924-24-8
• 化学式: C₈H₁₆ClMgN
• 分子量: 185.98
• InChiKey: OQCDKGPJPMOXAL-UHFFFAOYSA-M

计算性质

• 辛醇/水分配系数(LogP)：
  2.14
• 重原子数：
  11.0
• 可旋转键数：
  4.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  3.24
• 氢给体数：
  0.0
• 氢受体数：
  1.0

反应信息

• 作为反应物：
  描述：

  (3-Piperidiniopropyl)magnesiumchlorid 在 三乙胺 作用下， 以 四氢呋喃 、 苯 为溶剂， 反应 6.0h， 生成 2-(3-piperidinopropyl)tricyclo<3.3.1.1^3,7>decan-2-ol acetate
  参考文献：
  名称：

  New adamantan-2-ol and adamantan-1-methanol derivatives as potent antibacterials. Synthesis, antibacterial activity and lipophilicity studies

  摘要：

  Two series of active adamantane-group-bearing trialkylamines and their quaternary ammonium salts were synthesized and their biological properties were tested. One series includes 2-(3-dialkylaminopropyl)tricyclo[3.3.1.1(3,7)] decan-2-ols and the other alpha,alpha-bis(3-dialkylaminopropyl)tricyclo[3.3.1.1(3,7)]decyl/1-methanols. Some of the synthesized molecules proved to be very active anti bacterials. The minimum inhibitory concentration (MIG) values of the most potent compounds were determined. The observed differences were investigated. The antibacterial activity of the compounds was found to be enhanced as the length of the nitrogen-attached carbon chain extends from CH3 to C12H25. The lipophilicity of the synthesized molecules was also studied and its relationship with the antibacterial activity was investigated.

  DOI：

  10.1016/0223-5234(96)80443-0

文献信息

• Sila-Pharmaka, 33. Synthese und Eigenschaften des selektiven Antimuskarinikums Cyclohexylphenyl-(3-piperidinopropyl)silanol
  作者：Reinhold Tacke、Haryanto Linoh、Harald Zilch、Jürgen Wess、Ulrich Moser、Ernst Mutschler、Günter Lambrecht

  DOI：10.1002/jlac.198519851112

  日期：1985.11.12

  Die Synthese des selektiven Antimuskarinikums Cyclohexylphenyl(3-piperidinopropyl)silanol (1b) wird beschrieben. 1b wurde – ausgehend von (3-Chlorpropyl)trimethoxysilan – durch eine vierstufige Reaktionsfolge erhalten und als Hydrochlorid 2b mit einer Gesamt-ausbeute von etwa 45% isoliert. — 1b ist aufgrund seiner großen pharmakologischen Selektivität zu einer Standardsubstanz in der experimentellen

  描述了选择性抗毒蕈碱环己基苯基（3-哌啶子基丙基）硅烷醇（1b）的合成。通过四步反应序列，从（3-氯丙基）三甲氧基硅烷开始获得1b，并分离为盐酸盐2b，总收率约为45％。-1b由于其巨大的药理选择性，已成为区分毒蕈碱受体的实验药理学的标准物质。
• Cyclohexy (4-fluorophenyl)(3-piperidinopropyl)silanol ((itp)-fluoro-hexahydro-sila-difenidol, p-F-HSSiD) and derivatives: synthesis and antimuscarinic properties
  作者：Reinhold Tacke、Klaus Mahner、Carsten Strohmann、Bernhard Forth、Ernst Mutschler、Thomas Friebe、Günter Lambrecht

  DOI：10.1016/0022-328x(91)80194-o

  日期：1991.10

  Four different syntheses of the potent and selective muscarinic antagonist cyclohexyl(4-fluorophenyl)(3-piperidinopropyl)silanol (p-fluoro-hexahydro-sila-difenidol, p-F-HHSiD (2b); isolated as hydrochloride 2b.HCl) are described (starting materials: (CH3O)3SiCH2CH2CH2Cl and Si(OCH3)4). In addition, the synthesis of the corresponding carbon analogue p-fluoro-hexahydro-difenidol (p-F-HHD (2a); isolated as 2a.HCl) and the syntheses of three p-F-HHSiD derivatives (3-5), with a modified cyclic amino group, are reported (3: piperidino/pyrrolidino exchange, isolated as 3.HCl; 4: piperidino/hexamethylenimino exchange, isolated as 4.HCl; 5: quaternization of 2b with methyl iodide). The chiral compounds 2a, 2b, 3, 4 and 5 were prepared as racemates. In functional pharmacological studies, 3-5 behaved as simple competitive antagonists at muscarinic M1 receptors in rabbit vas deferens, M2 receptors in guinea-pig atria, and M3 receptors in guinea-pig ileal smooth muscle. The pyrrolidino (3) and hexamethylenimino (4) analogues of the parent drug p-F-HHSiD (2b) displayed the highest affinity for M1 and M3 receptors (pA2 values: 7.0-7.4) but exhibited lower affinity for cardiac M2 receptors (pA2: 5.9 and 6.0). Their affinity profile (M1 approximately M3 > M2) is different from that of p-F-HHSiD (2b) (M3 > M1 > M2), but qualitatively very similar to that of p-F-HHD (2a). The methiodide 5 exhibited the highest affinity for M1 receptors (pA2: 8.5) but lower affinity for M2 and M3 receptors by factors of 5.6 and 3.6, respectively.
• TACKE, R.;LINOH, H.;ZILCH, H.;WESS, J.;MOSER, U.;MUTSCHLER, F.;LAMBRECHT,+, LIEBIGS ANN. CHEM., 1985, N 11, 2223-2228
  作者：TACKE, R.、LINOH, H.、ZILCH, H.、WESS, J.、MOSER, U.、MUTSCHLER, F.、LAMBRECHT,+

  DOI：——

  日期：——
• US3937833A
  申请人：——

  公开号：US3937833A

  公开（公告）日：1976-02-10
• US4041165A
  申请人：——

  公开号：US4041165A

  公开（公告）日：1977-08-09