6-m-tolyl-2,3,4,5-tetrahydropyridine

• 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: 6-m-tolyl-2,3,4,5-tetrahydropyridine
• 英文别名: 6-(M-tolyl)-2,3,4,5-tetrahydropyridine；6-(3-methylphenyl)-2,3,4,5-tetrahydropyridine
• 化学式: C₁₂H₁₅N
• 分子量: 173.258
• InChiKey: BUUFQMSIVSLYGH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  13
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  12.4
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  6-m-tolyl-2,3,4,5-tetrahydropyridine 在 bis(1,5-cyclooctadiene)diiridium(I) dichloride 、 (R,R)-f-spiroPhos 、 氢气 作用下， 以 1,4-二氧六环 为溶剂， 50.0 ℃ 、5.07 MPa 条件下， 反应 24.0h， 以95%的产率得到(S)-2-(M-Tolyl)piperidine
  参考文献：
  名称：

  通过Ir催化的环亚胺的对映选择性加氢 合成手性环胺†

  摘要：

  已经实现了用于合成手性环状胺的环状亚胺的高度对映选择性氢化。以铱和（R，R）-f-spiroPhos的络合物为催化剂，在不添加任何添加剂的情况下，将一系列环状2-芳基亚胺在温和条件下平稳氢化，从而提供相应的手性环状胺，对映选择性高达98 ％ee。而且，该方法可以成功地应用于（+）-（6 S，10b R）-McN-4612-Z的合成。

  DOI：

  10.1039/c7ob00442g
• 作为产物：
  描述：

  5-溴戊腈 、 3-溴甲基苯 在 magnesium 作用下， 以 四氢呋喃 为溶剂， 反应 1.0h， 以38%的产率得到6-m-tolyl-2,3,4,5-tetrahydropyridine
  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

文献信息

• SUBSTITUTED PHENYL ACETIC ACIDS AS DP-2 ANTAGONISTS
  申请人：ICOS CORPORATION

  公开号：EP2044017A2

  公开（公告）日：2009-04-08
• [EN] SUBSTITUTED PHENYL ACETIC ACIDS AS DP-2 ANTAGONISTS<br/>[FR] ACIDES PHÉNYLACÉTIQUES SUBSTITUÉS UTILISÉS EN TANT QU'ANTAGONISTES DE DP-2
  申请人：ICOS CORP

  公开号：WO2007146838A2

  公开（公告）日：2007-12-21

  [EN] Substituted phenyl acetic acid compounds of formula I, pharmaceutical compositions, methods for their preparation and methods are provided that are useful in the treatment and prevention of disorders or conditions responsive to DP-2 receptor modulation, in particular, inflammatory and immune related disorders and conditions, such as asthma, allergic rhinitis and atopic dermatitis.
  [FR] La présente invention concerne des composés d'acide phénylacétique substitués répondant à la formule I, des compositions pharmaceutiques, des procédés permettant leur préparation et des procédés qui se révèlent utiles pour le traitement et la prévention de troubles ou de pathologies sensibles à une modulation du récepteur de DP-2, en particulier, des troubles et des pathologies inflammatoires et immunitaires, tels que l'asthme, la rhinite allergique et la dermatite atopique.
• 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.
• Synthesis of chiral cyclic amines via Ir-catalyzed enantioselective hydrogenation of cyclic imines
  作者：Ying Zhang、Duanyang Kong、Rui Wang、Guohua Hou

  DOI：10.1039/c7ob00442g

  日期：——

  A highly enantioselective hydrogenation of cyclic imines for synthesis of chiral cyclic amines has been realized. With the complex of iridium and (R,R)-f-spiroPhos as the catalyst, a range of cyclic 2-aryl imines were smoothly hydrogenated under mild conditions without any additive to provide the corresponding chiral cyclic amines with excellent enantioselectivities of up to 98% ee. Moreover, this

  已经实现了用于合成手性环状胺的环状亚胺的高度对映选择性氢化。以铱和（R，R）-f-spiroPhos的络合物为催化剂，在不添加任何添加剂的情况下，将一系列环状2-芳基亚胺在温和条件下平稳氢化，从而提供相应的手性环状胺，对映选择性高达98 ％ee。而且，该方法可以成功地应用于（+）-（6 S，10b R）-McN-4612-Z的合成。