(5-oxo-5-(3-methoxyphenyl)-pentyl)-carbamic acid tert-butyl ester | 616226-78-9

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (5-oxo-5-(3-methoxyphenyl)-pentyl)-carbamic acid tert-butyl ester
• 英文别名: tert-butyl 5-(3-methoxyphenyl)-5-oxopentylcarbamate；5-(N-Boc-amino)-3'-methoxypentanophenone；tert-butyl N-[5-(3-methoxyphenyl)-5-oxopentyl]carbamate
• CAS: 616226-78-9
• 化学式: C₁₇H₂₅NO₄
• 分子量: 307.39
• InChiKey: WAPWHLZTPPUTHF-UHFFFAOYSA-N

物化性质

• 沸点：
  451.2±25.0 °C(Predicted)
• 密度：
  1.062±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  22
• 可旋转键数：
  9
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.53
• 拓扑面积：
  64.6
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (5-oxo-5-(3-methoxyphenyl)-pentyl)-carbamic acid tert-butyl ester 在 氢溴酸 、 三氟乙酸 作用下， 以 水 为溶剂， 反应 18.0h， 生成 3-(3,4,5,6-tetrahydropyridin-2-yl)phenol
  参考文献：
  名称：

  Modification of the anabaseine pyridine nucleus allows achieving binding and functional selectivity for the α3β4 nicotinic acetylcholine receptor subtype

  摘要：

  We report the design, synthesis and pharmacological screening of a group of analogues of anabaseine 2, a naturally occurring unselective nicotinic agonist. The novel nAChR ligands 5-15 were planned following a molecular modeling analysis which suggested the replacement of the pyridine ring of 2 with a 3 substituted benzene ring as a means to gain selectivity for the alpha 3 beta 4 nAChR subtype. Overall, from binding experiments, the synthesized compounds showed high values of alpha 3 beta 4 affinity and alpha 3 beta 4 vs alpha 3 beta 4 selectivity, although they poorly discriminated the homomeric alpha 7 subtype. The three analogues 6,12 and 13 were also evaluated in electrophysiological assays, and 12 [6-(3-iodophenyl)-2,3,4,5-tetrahydropyridine] emerged as a rather interesting nicotinic ligand. Indeed, in addition to a note-worthy affinity (K-i = 4.7 nM) for the alpha 3 beta 4 subtype and to an excellent alpha 3 beta 4 vs alpha 3 beta 4 subtype selectivity (806 -fold), compound 12 selectively activated the alpha 3 beta 4 nAChR (EC50 = 7.4 mu M) while eliciting a negligible response at the alpha 7 subtype and no effect at the alpha 3 beta 4 subtype. (C) 2015 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2015.11.045
• 作为产物：
  描述：

  二碳酸二叔丁酯 在 正丁基锂 、 碘 、 magnesium 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 1.0h， 生成 (5-oxo-5-(3-methoxyphenyl)-pentyl)-carbamic acid tert-butyl ester
  参考文献：
  名称：

  A One-Pot Process for the Enantioselective Synthesis of Amines via Reductive Amination under Transfer Hydrogenation Conditions

  摘要：

  Cyclic amines may be prepared via a sequence of deprotection followed by intramolecular reductive amination of t-Boc-protected amino ketones under asymmetric transfer hydrogenation conditions. In cases where the corresponding imine reaction proceeds with high enantioselectivity, this is reflected in the one-step process.

  DOI：

  10.1021/ol035746r

文献信息

• Modification of the anabaseine pyridine nucleus allows achieving binding and functional selectivity for the α3β4 nicotinic acetylcholine receptor subtype
  作者：Carlo Matera、Marta Quadri、Miriam Sciaccaluga、Diego Yuri Pomè、Francesca Fasoli、Marco De Amici、Sergio Fucile、Cecilia Gotti、Clelia Dallanoce、Giovanni Grazioso

  DOI：10.1016/j.ejmech.2015.11.045

  日期：2016.1

  We report the design, synthesis and pharmacological screening of a group of analogues of anabaseine 2, a naturally occurring unselective nicotinic agonist. The novel nAChR ligands 5-15 were planned following a molecular modeling analysis which suggested the replacement of the pyridine ring of 2 with a 3 substituted benzene ring as a means to gain selectivity for the alpha 3 beta 4 nAChR subtype. Overall, from binding experiments, the synthesized compounds showed high values of alpha 3 beta 4 affinity and alpha 3 beta 4 vs alpha 3 beta 4 selectivity, although they poorly discriminated the homomeric alpha 7 subtype. The three analogues 6,12 and 13 were also evaluated in electrophysiological assays, and 12 [6-(3-iodophenyl)-2,3,4,5-tetrahydropyridine] emerged as a rather interesting nicotinic ligand. Indeed, in addition to a note-worthy affinity (K-i = 4.7 nM) for the alpha 3 beta 4 subtype and to an excellent alpha 3 beta 4 vs alpha 3 beta 4 subtype selectivity (806 -fold), compound 12 selectively activated the alpha 3 beta 4 nAChR (EC50 = 7.4 mu M) while eliciting a negligible response at the alpha 7 subtype and no effect at the alpha 3 beta 4 subtype. (C) 2015 Elsevier Masson SAS. All rights reserved.
• A One-Pot Process for the Enantioselective Synthesis of Amines via Reductive Amination under Transfer Hydrogenation Conditions
  作者：Glynn D. Williams、Richard A. Pike、Charles E. Wade、Martin Wills

  DOI：10.1021/ol035746r

  日期：2003.10.1

  Cyclic amines may be prepared via a sequence of deprotection followed by intramolecular reductive amination of t-Boc-protected amino ketones under asymmetric transfer hydrogenation conditions. In cases where the corresponding imine reaction proceeds with high enantioselectivity, this is reflected in the one-step process.