8-methoxy1-phenyl-2,3,4,5-tetrahydro-1H-3-benzazepine | 62717-61-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯氮卓类
• 英文名称: 8-methoxy1-phenyl-2,3,4,5-tetrahydro-1H-3-benzazepine
• 英文别名: 8-methoxy-1-phenyl-2,3,4,5-tetrahydro-1H-benzo[d]azepine；8-methoxy-1-phenyl-2,3,4,5-tetrahydro-1H-3-benzazepine；8-methoxy-1-phenyl-2,3,4,5-tetrahydro-3H-benzazepine；8-Methoxy-1-phenyl-2,3,4,5-tetrahydro-1H-3-benzazepin；1-Phenyl-7-methoxy-2,3,4,5-tetrahydro-3,1-benzazepin；7-methoxy-5-phenyl-2,3,4,5-tetrahydro-1H-3-benzazepine
• CAS: 62717-61-7
• 化学式: C₁₇H₁₉NO
• 分子量: 253.344
• InChiKey: PIEOYUKTDZQDKN-UHFFFAOYSA-N

物化性质

• 沸点：
  397.3±42.0 °C(Predicted)
• 密度：
  1.063±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  19
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  21.3
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  8-methoxy1-phenyl-2,3,4,5-tetrahydro-1H-3-benzazepine 在 三溴化硼 作用下， 以 二氯甲烷 、 氯仿 为溶剂， 生成 SKF 77174
  参考文献：
  名称：

  Exploring the Structure−Activity Relationship of the Ethylamine Portion of 3-Iodothyronamine for Rat and Mouse Trace Amine-Associated Receptor 1

  摘要：

  3-Iodothyronamine (1, T(1)AM) is a naturally occurring derivative of thyroid hormone that can potently activate the orphan G protein-coupled receptor (GPCR) known as the trace amine-associated receptor 1 (TAAR(1)). We have previously found that modifying the outer ring of the phenoxyphenethylamine core scaffold of 1 can improve potency and provide potent agonists. In this study, we explored the tolerance of rat and mouse TAAR(1) (rTAAR(1) and mTAAR(1)) for structural modifications in the ethylamine portion of 1. We found that incorporating unsaturated hydrocarbon substituents and polar, hydrogen-bond-accepting groups were beneficial for rTAAR(1) and mTAAR(1), respectively, providing compounds that were equipotent or more potent than 1. Additionally, we have discovered that a naphthyl group is an excellent isosteric replacement for the iodophenyl ring of 1.

  DOI：

  10.1021/jm0700417
• 作为产物：
  描述：

  2-(4-甲氧苯基)乙胺 在 硫酸 、 三氟乙酸 作用下， 反应 19.0h， 生成 8-methoxy1-phenyl-2,3,4,5-tetrahydro-1H-3-benzazepine
  参考文献：
  名称：

  (.+-.)-3-Allyl-7-halo-8-hydroxy-1-phenyl-2,3,4,5-tetrahydro-1H-3-benzazepines as selective high affinity D1 dopamine receptor antagonists: synthesis and structure-activity relationship

  摘要：

  Substituted 1-phenyl-3-benzazepines form a class of compounds possessing potent and selective affinity for the D1 DA receptor. 7,8-Dihydroxy-1-phenyl-2,3,4,5-tetrahydro-1H-3-benzazepine (SKF 38393) and its 6-halo analogues are potent and selective D1 receptor agonists. Recently, the 3-allyl derivatives of SKF 38393 and its analogues were described as selective D1 agonists with higher D1 efficacy and CNS potency. In order to extend these results to compounds in the 7-halo-8-hydroxy-substituted antagonist series, we have synthesized and pharmacologically characterized 3-allyl analogues of 7-substituted (Cl, Br, H) 8-hydroxy-1-phenyl-2,3,4,5-tetrahydro-1H-3-benzazepines. These 3-allyl derivatives were compared with their 3-methyl and 3-unsubstituted analogues in terms of their D1 receptor affinity and selectivity. The results have been used to generate structure-affinity relationships. The D1 receptor affinity, for 3-substitution, is found to be in the order: methyl > allyl > H. For 7-substitution, the affinity is in the order: Cl = Br > H. The 3-allyl compounds show affinity close to that of the parent (3-methyl) compounds while exhibiting a slightly diminished D1 selectivity. However, the greater lipophilicity of the 3-allyl compounds may enable them to cross the blood-brain barrier more readily and thereby exhibit higher in vivo CNS potency. Thus 3-allylbenzazepines have potential as high affinity selective Dl antagonists.

  DOI：

  10.1021/jm00079a008

文献信息

• Urea derivative useful as an anti-cancer agent and process for preparing same
  申请人：Chaconne Nsi Co., Ltd.

  公开号：US20020019389A1

  公开（公告）日：2002-02-14

  The present invention relates to a novel urea derivative represented by the following formula (I), which is useful as an anti-cancer agent: 1 its pharmaceutically acceptable acid addition salt or stereoisomer, in which X, Y, B and Het have the meaning as defined in the specification, and to a process for preparing the compound of formula (I) and an anti-cancer composition comprising the compound of formula (I) as an active ingredient.

  本发明涉及一种新颖的尿素衍生物，其化学式如下（I），可用作抗癌剂：其药学上可接受的酸盐或立体异构体，其中X、Y、B和Het的含义如规范中所定义，并且涉及制备化合物的公式（I）以及包含公式（I）化合物作为活性成分的抗癌组合物的方法。
• Palladium-Catalyzed Regio- and Stereoselective γ-Arylation of Tertiary Allylic Amines: Identification of Potent Adenylyl Cyclase Inhibitors
  作者：Zhishi Ye、Tarsis F. Brust、Val J. Watts、Mingji Dai

  DOI：10.1021/ol503748t

  日期：2015.2.20

  Substituted allylic amines and their derivatives are key structural motifs of many drug molecules and natural products. A general, mild, and practical palladium-catalyzed γ-arylation of tertiary allylic amines, one of the most challenging Heck arylation substrates, has been developed. The γ-arylation products were obtained in excellent regio- and stereoselectivity. Moreover, novel and potent adenylyl

  取代的烯丙基胺及其衍生物是许多药物分子和天然产物的关键结构图案。已开发出一般，温和且实用的叔烯丙基胺的钯催化γ-芳基化反应，这是最具挑战性的Heck芳基化底物之一。γ-芳基化产物以优异的区域选择性和立体选择性获得。此外，已经从γ-芳基化产物中鉴定出了新型和有效的腺苷酸环化酶抑制剂，其具有治疗神经性和炎性疼痛的潜力。
• Copper-Catalyzed Cyclopropanol Ring Opening C_sp³–C_sp³ Cross-Couplings with (Fluoro)Alkyl Halides
  作者：Zhishi Ye、Kristen E. Gettys、Xingyu Shen、Mingji Dai

  DOI：10.1021/acs.orglett.5b03096

  日期：2015.12.18

  copper-catalyzed cyclopropanol ring opening cross-coupling reactions with difluoroalkyl bromides, perfluoroalkyl iodides, monofluoroalkyl bromides, and 2-bromo-2-alkylesters to synthesize various β-(fluoro)alkylated ketones are reported. The reactions feature mild conditions and excellent functional group compatibility and can be scaled up to gram scale. Preliminary mechanistic studies suggest the involvement

  报道了新型和通用的铜催化环丙醇与二氟烷基溴、全氟烷基碘、单氟烷基溴和2-溴-2-烷基酯的开环交叉偶联反应，合成各种β-(氟)烷基化酮。该反应条件温和，官能团相容性好，可放大至克级。初步的机理研究表明自由基中间体的参与。利用环丙醇开环产生的羰基，二氟烷基-烷基交叉偶联产物还可以很容易地转化为更有价值和更多样化的含偕二氟化合物。
• 1-phenyl-3-benzazepines and their use for treating gastrointestinal
  申请人：Smithkline Beckman Corporation

  公开号：US04707483A1

  公开（公告）日：1987-11-17

  1-Phenyl-3-benzazepine compounds are useful in treating gastrointestinal motility disorders. A particular compound of this invention is 8-hydroxy-3-methyl-1-phenyl-7-phenylthio-2,3,4,5-tetrahydro-1H-3-benzazepi ne.

  1-苯基-3-苯基吖啶类化合物在治疗胃肠动力障碍方面很有用。这项发明的一种特定化合物是8-羟基-3-甲基-1-苯基-7-苯硫基-2,3,4,5-四氢-1H-3-苯基吖啶。
• An Umpolung Strategy for the Synthesis of β-Aminoketones via Copper-Catalyzed Electrophilic Amination of Cyclopropanols
  作者：Zhishi Ye、Mingji Dai

  DOI：10.1021/acs.orglett.5b00828

  日期：2015.5.1

  A novel copper-catalyzed electrophilic amination of cyclopropanols with O-benzoyl-N,N-dialkylhydroxylamines to synthesize various β-aminoketones via a sequence that includes C–C bond cleavage and Csp3–N bond formation is reported. The reaction conditions are mild and tolerate a wide range of functional groups including benzoate, tosylate, expoxide, and α,β-unsaturated carbonyls, which are incompatible

  报道了一种新颖的铜催化的环丙醇与邻苯甲酰基-N，N-二烷基羟胺的亲电胺化反应，可通过包括C-C键断裂和C sp 3 -N键形成的序列合成各种β-氨基酮。反应条件温和，可耐受各种官能团，包括苯甲酸酯，甲苯磺酸酯，环氧化合物和α，β-不饱和羰基，它们在传统的胺亲核共轭物加成反应和曼尼希反应条件下不相容。还已经描述了该蛋白酚β-氨基酮合成方法的初步机理研究和提议的催化循环。