6,7,8,9-四氢-5H-吡啶并[3,4-c]氮杂卓 | 185510-15-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吖庚因类
• 中文名称: 6,7,8,9-四氢-5H-吡啶并[3,4-c]氮杂卓
• 英文名称: 6,7,8,9-tetrahydro-5H-pyrido<3,4-c>azepine
• 英文别名: 6,7,8,9-Tetrahydro-5H-pyrido[3,4-c]azepine
• CAS: 185510-15-0
• 化学式: C₉H₁₂N₂
• mdl: MFCD18821688
• 分子量: 148.208
• InChiKey: FCICAJXRVMPKJZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.6
• 重原子数：
  11
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.444
• 拓扑面积：
  24.9
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  草酸 、 6,7,8,9-四氢-5H-吡啶并[3,4-c]氮杂卓 以 乙醚 为溶剂， 生成 6,7,8,9-tetrahydro-5H-pyrido<3,4-c>azepine dioxalate
  参考文献：
  名称：

  Synthesis and binding of 6,7,8,9-tetrahydro-5H-pyrido[3,4-d]azepine and related ring-opened analogs at central nicotinic receptors

  摘要：

  6,7,8,9-Tetrahydro-5H-pyrido[3,4-d]azepine (5a) and its N-7-methyl derivative 5b were synthesized and evaluated as potential nicotinic acetylcholinergic receptor (nAChR) ligands. On the basis that 6,7,8,9-tetrahydro-5H-pyrido[3,4-c]azepine (4a), which binds at nAChRs with low affinity (K-i = 1100 nM), possesses an internitrogen distance (4.6 Angstrom) that may be less than optimal, we designed compound 5a due to its similar shape but longer internitrogen distance (5.5 Angstrom). Compound 5a (K-i = 45 nM) was found to bind with enhanced affinity. However, unlike what is seen with nornicotine/nicotine, N-methylation of 5a reduced affinity (5b; K-i = 268 nM) rather than enhancing it. The results suggest that 5 may interact at nicotine receptors in a manner that is somewhat different from that of nicotine. Ring-opening of the pyrido[3,4-d]azepine ring led to a series of 3-(2-aminoethyl)pyridines 21 that retained the affinity of the cyclic compound. Subsequent modification, including further chain lengthening (e.g. aminopropylpyridines 22) and introduction of unsaturation, ultimately led to the development of a series of 3-(2-aminethoxy)pyridines 27. Simple N-substituted derivatives of 27 were found to bind with K-i values of 20 to 35 nM. Because parallel structural changes in several series of related compounds did not result in parallel shifts in nAChR affinity, it is unlikely that all the investigated compounds bind in a similar fashion at these receptors. Nevertheless, some of these compounds represent novel classes of nAChR ligands. (C) Elsevier, Paris.

  DOI：

  10.1016/s0223-5234(99)80051-8
• 作为产物：
  描述：

  6,7,8,9-tetrahydro-5H-pyrido<3,4-c>azepin-7-one 在 lithium aluminium tetrahydride 作用下， 以 四氢呋喃 为溶剂， 反应 1.0h， 生成 6,7,8,9-四氢-5H-吡啶并[3,4-c]氮杂卓
  参考文献：
  名称：

  Synthesis and binding of 6,7,8,9-tetrahydro-5H-pyrido[3,4-d]azepine and related ring-opened analogs at central nicotinic receptors

  摘要：

  6,7,8,9-Tetrahydro-5H-pyrido[3,4-d]azepine (5a) and its N-7-methyl derivative 5b were synthesized and evaluated as potential nicotinic acetylcholinergic receptor (nAChR) ligands. On the basis that 6,7,8,9-tetrahydro-5H-pyrido[3,4-c]azepine (4a), which binds at nAChRs with low affinity (K-i = 1100 nM), possesses an internitrogen distance (4.6 Angstrom) that may be less than optimal, we designed compound 5a due to its similar shape but longer internitrogen distance (5.5 Angstrom). Compound 5a (K-i = 45 nM) was found to bind with enhanced affinity. However, unlike what is seen with nornicotine/nicotine, N-methylation of 5a reduced affinity (5b; K-i = 268 nM) rather than enhancing it. The results suggest that 5 may interact at nicotine receptors in a manner that is somewhat different from that of nicotine. Ring-opening of the pyrido[3,4-d]azepine ring led to a series of 3-(2-aminoethyl)pyridines 21 that retained the affinity of the cyclic compound. Subsequent modification, including further chain lengthening (e.g. aminopropylpyridines 22) and introduction of unsaturation, ultimately led to the development of a series of 3-(2-aminethoxy)pyridines 27. Simple N-substituted derivatives of 27 were found to bind with K-i values of 20 to 35 nM. Because parallel structural changes in several series of related compounds did not result in parallel shifts in nAChR affinity, it is unlikely that all the investigated compounds bind in a similar fashion at these receptors. Nevertheless, some of these compounds represent novel classes of nAChR ligands. (C) Elsevier, Paris.

  DOI：

  10.1016/s0223-5234(99)80051-8

文献信息

• Process for preparing substituted biphenyls
  申请人：BASF SE

  公开号：US10683256B2

  公开（公告）日：2020-06-16

  The present invention relates to a process for preparing substituted biphenyls via Suzuki coupling using specific phosphorus ligands and a solvent mixture containing water, a non-polar organic solvent and a polar aprotic co-solvent.

  本发明涉及一种利用特定磷配体和含有水、非极性有机溶剂和极性钝化助溶剂的混合溶剂，通过铃木偶联制备取代联苯的工艺。
• Organic reactions carried out in aqueous solution in the presence of a hydroxyalkyl(alkyl)cellulose or an alkylcellulose
  申请人：AbbVie Deutschland GmbH & Co. KG

  公开号：US10836688B2

  公开（公告）日：2020-11-17

  The present invention relates to a method of carrying out an organic reaction in aqueous solution in the presence of a hydroxyalkyl(alkyl)cellulose or an alkylcellulose.

  本发明涉及一种在有羟基烷基纤维素或烷基纤维素存在的水溶液中进行有机反应的方法。
• Stabilizer composition
  申请人：BASF SE

  公开号：US11001698B2

  公开（公告）日：2021-05-11

  The present invention relates to a stabilizer composition containing at least one sterically hindered amine (HALS) in which the amino group carries a basicity-reducing substituent, at least one antioxidant containing one or more thioether groups and at least one liquid plasticizer containing carboxylate groups. The invention further relates to a polymer composition containing at least one sterically hindered amine (HALS) in which the amino group carries a basicity-reducing substituent, at least one antioxidant containing one or more thioether groups, at least one liquid plasticizer containing carboxylate groups and at least one silyl-terminated polymer, to the use of the stabilizer composition for stabilizing a silyl-terminated polymer or a sealant, adhesive, gasket, knifing filler or coating composition, especially a sealant, adhesive, gasket, knifing filler or coating composition containing a silyl-terminated polymer, against degradation by heat, light and/or oxygen, to the use of the polymer composition as or in a sealant, adhesive, liquid gasket, knifing filler or coating composition, and to a sealant composition or an adhesive composition, or a gasket composition, or a knifing filler composition or a coating composition comprising the polymer composition.

  本发明涉及一种稳定剂组合物，其中至少含有一种氨基带有还原碱性取代基的立体受阻胺（HALS）、至少一种含有一个或多个硫醚基团的抗氧化剂和至少一种含有羧酸基团的液体增塑剂。本发明还涉及一种聚合物组合物，该组合物含有至少一种氨基带有碱性还原取代基的立体受阻胺 （HALS）、至少一种含有一个或多个硫醚基团的抗氧化剂、至少一种含有羧酸基团的液体增塑剂和至少一种硅烷封端聚合物，该稳定剂组合物可用于稳定硅烷封端聚合物或密封剂、粘合剂、垫圈、刀具填料或涂层组合物、稳定剂组合物用于稳定密封剂、粘合剂、垫片、切削填充剂或涂层组合物，特别是含有硅烷基封端聚合物的密封剂、粘合剂、垫片、切削填充剂或涂层组合物，使其不受热、光和/或氧的影响而降解；稳定聚合物组合物作为密封剂、粘合剂、液体垫片、切削填充剂或涂层组合物或在其中使用；稳定包含聚合物组合物的密封剂组合物、粘合剂组合物、垫片组合物、切削填充剂组合物或涂层组合物。
• Pyrrolidine-modified and 6-substituted analogs of nicotine: A structure—affinity investigation
  作者：M Dukat、W Fiedler、D Dumas、I Damaj、BR Martin、JA Rosecrans、JR James、RA Glennon

  DOI：10.1016/s0223-5234(97)89850-9

  日期：1996.1

  Because the structural requirements for the binding of nicotine to central nicotine receptors remain largely uninvestigated, we undertook a systematic investigation of pyrrolidine ring-opened analogs. This led to a subsequent investigation of related conformationally restricted derivatives of these analogs. The results are reported relative to the binding of several well-known and widely used nicotine receptor ligands. Although none of the ring-opened analogs binds with higher affinity than (-)nicotine (K-i = 2.3 nM), 3-(N-methyl-N-ethylaminomethyl)pyridine (12a; K-i = 28 nM) binds with significant affinity. A conformationally restricted analog of 12a, N-methyl [2,7]naphthyridine 30b (K-i = 18 nM), binds with similar affinity. 6-Substitution of 12a and racemic nicotine seems to be tolerated when the substituent is halogen or methyl. In functional studies (hypolocomotion and antinociception in mice; stimulus generalization in nicotine-trained rats) 30b retains nicotine-like properties. Several of the 6-substituted compounds were 2 to 20 times more potent than (+/-)nicotine. Although the intact pyrrolidine ring of nicotine appears important for optimal affinity, its pre presence is not an absolute requirement for activity, and 6-position substitution of the pyridine nucleus can influence both binding and functional activity.
• ORGANIC REACTIONS CARRIED OUT IN AQUEOUS SOLUTION IN THE PRESENCE OF A HYDROXYALKYL(ALKYL)CELLULOSE OR AN ALKYLCELLULOSE
  申请人：AbbVie Deutschland GmbH & Co. KG

  公开号：US20170217850A1

  公开（公告）日：2017-08-03

  The present invention relates to a method of carrying out an organic reaction in aqueous solution in the presence of a hydroxyalkyl(alkyl)cellulose or an alkylcellulose.