1-benzyl-1,2,3,6-tetrahydropyridine-4-carboxylic acid amide | 70638-26-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 1-benzyl-1,2,3,6-tetrahydropyridine-4-carboxylic acid amide
• 英文别名: 1-benzyl-4-carbamoyl-1,2,5,6-tetrahydropyridine；4-Aminocarbonyl-N-benzyl-1,2,5,6-tetrahydropyridin；1-Benzyl-1,2,3,6-tetrahydropyridine-4-carboxamide；1-benzyl-3,6-dihydro-2H-pyridine-4-carboxamide
• CAS: 70638-26-5
• 化学式: C₁₃H₁₆N₂O
• 分子量: 216.283
• InChiKey: JBOPHYZVNHQCJR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1
• 重原子数：
  16
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  46.3
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  1-benzyl-1,2,3,6-tetrahydropyridine-4-carboxylic acid amide 在 sodium hydroxide 、 磺酰氯 、 氢溴酸 、 双氧水 作用下， 以 水 、 溶剂黄146 、 乙酸乙酯 、 1,2-二氯乙烷 为溶剂， 反应 176.0h， 生成 4,5,6,7-tetrahydroisothiazolo[5,4-c]pyridin-3-ol hydrobromide
  参考文献：
  名称：

  Aza-THIP and related analogues of THIP as GABA C antagonists

  摘要：

  The potency of a series of eight compounds structurally related with 4,5,6,7-tetrahydroisoxazolo[5,4-c]pyridin-3-ol (THIP), a potent GABA(A) partial agonist exhibiting GABA(C) rho(1) antagonist effect (K-i = 25 muM), was determined electrophysiologically using homomeric human GABA(C) rho(1) receptors expressed in Xenopus oocytes. Protolytic properties (pK(a) values for the acidic bioisosteric groups) and the presence of steric bulk in the molecules appear to be structural parameters of importance for blockade of the GABA(C) rho(1) receptor. Within this series of moderately potent GABA(C) antagonists, only 4,5,6,7-tetrahydropyrazolo[5,4-c]pyridin-3-ol (Aza-THIP) does not interact delectably with GABA(A) receptors, and Aza-THIP has the potential of being a useful tool for molecular and behavioural pharmacological studies. (C) 2003 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2003.09.016
• 作为产物：
  描述：

  4-吡啶甲酰胺 在 sodium tetrahydroborate 作用下， 以 甲醇 、 乙醇 为溶剂， 反应 23.5h， 生成 1-benzyl-1,2,3,6-tetrahydropyridine-4-carboxylic acid amide
  参考文献：
  名称：

  Aza-THIP and related analogues of THIP as GABA C antagonists

  摘要：

  The potency of a series of eight compounds structurally related with 4,5,6,7-tetrahydroisoxazolo[5,4-c]pyridin-3-ol (THIP), a potent GABA(A) partial agonist exhibiting GABA(C) rho(1) antagonist effect (K-i = 25 muM), was determined electrophysiologically using homomeric human GABA(C) rho(1) receptors expressed in Xenopus oocytes. Protolytic properties (pK(a) values for the acidic bioisosteric groups) and the presence of steric bulk in the molecules appear to be structural parameters of importance for blockade of the GABA(C) rho(1) receptor. Within this series of moderately potent GABA(C) antagonists, only 4,5,6,7-tetrahydropyrazolo[5,4-c]pyridin-3-ol (Aza-THIP) does not interact delectably with GABA(A) receptors, and Aza-THIP has the potential of being a useful tool for molecular and behavioural pharmacological studies. (C) 2003 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2003.09.016

文献信息

• Cu-Catalyzed C–H Alkenylation of Benzoic Acid and Acrylic Acid Derivatives with Vinyl Boronates
  作者：Jian-Jun Li、Cheng-Gang Wang、Jin-Feng Yu、Peng Wang、Jin-Quan Yu

  DOI：10.1021/acs.orglett.0c01469

  日期：2020.6.19

  An efficient Cu-catalyzed C–H alkenylation with acyclic and cyclic vinyl boronates was realized for the first time under mild conditions. The scope of the vinyl borons and the compatibility with functional groups including heterocycles are superior than Pd-catalyzed C–H coupling with vinyl borons, providing a reliable access to multisubstituted alkenes and dienes. Subsequent hydrogenation of the product

  在温和条件下，首次实现了具有无环和环状硼酸乙烯基酯的高效Cu催化的CH链烯基化。乙烯基硼的范围以及与包括杂环在内的官能团的相容性均优于Pd催化的CH-H与乙烯基硼的偶联，为多取代烯烃和二烯的可靠获得提供了条件。随后从内部乙烯基硼中氢化产物将导致仲烷基的安装。
• Paglietti, Giuseppe; Sanna, Paolo; Nuvole, Antonio, Journal of Chemical Research, Miniprint, 1983, # 10, p. 2326 - 2342
  作者：Paglietti, Giuseppe、Sanna, Paolo、Nuvole, Antonio、Soccolini, Francesco、Acheson, R. Morrin

  DOI：——

  日期：——
• PAGLIETTI, G.;SANNA, P.;NUVOLE, A.;SOCCOLINI, F.;ACHESON, R. M., J. CHEM. RES. MICROFICHE, 1983, N 10, 245
  作者：PAGLIETTI, G.、SANNA, P.、NUVOLE, A.、SOCCOLINI, F.、ACHESON, R. M.

  DOI：——

  日期：——
• HUTCHINS R. O.; NATALE N. R., SYNTHESIS, 1979, NO 4, 281-283,
  作者：HUTCHINS R. O.、 NATALE N. R.

  DOI：——

  日期：——