2-(3,4-dihydro-7-methoxy-1(2H)-naphthalenylidene)ethanamine | 468104-18-9

• 物质功能分类: 分析化学 - 标准品 - 药典标准品和杂质标准品
• 分子结构分类: 有机化合物 - 苯类化合物 - 四氢化萘
• 英文名称: 2-(3,4-dihydro-7-methoxy-1(2H)-naphthalenylidene)ethanamine
• 英文别名: 1-(2-Aminoethylidene)-7-methoxy-1,2,3,4-tetrahydronaphthalene；2-(7-methoxy-3,4-dihydro-2H-naphthalen-1-ylidene)ethanamine
• CAS: 468104-18-9
• 化学式: C₁₃H₁₇NO
• 分子量: 203.284
• InChiKey: MWEUQVRSDPFXDI-UHFFFAOYSA-N

物化性质

• 沸点：
  367.8±37.0 °C(Predicted)
• 密度：
  1.122±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  15
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  35.2
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  2-(3,4-dihydro-7-methoxy-1(2H)-naphthalenylidene)ethanamine 在 5% Pd on active carbon 氢气 、 三乙胺 作用下， 以 四氢呋喃 为溶剂， 生成 7-methoxy-1-[2-(trifluoroacetylamino)ethyl]-1,2,3,4-tetrahydronaphthalene
  参考文献：
  名称：

  Synthesis of a Novel Series of Benzocycloalkene Derivatives as Melatonin Receptor Agonists

  摘要：

  We synthesized a novel series of benzocycloalkene derivatives and evaluated their binding affinities to melatonin receptors. To control the spatial position of the amide group, one of the important pharmacophores, we incorporated an endo double bond, an exo double bond (E- and Z-configurations), and a chiral center (R- and S-configurations) at position 1. The indan derivatives with the S-configuration at position 1 were the most promising in terms of potency and selectivity for the human melatonin receptor (MT, site), while compounds with the R-configuration showed little potential. Our next attempt was to investigate the most favorable conformation of the methoxy group, the other important pharmacophore for binding to the MT, receptor. The introduction of a methyl group at position 5 of the indene ring conserved affinity; however, at position 7, it caused a decrease in affinity. These results suggested that the substitution at position 7 forced the methoxy group to adopt an unfavorable orientation. The optimization of the condensed ring size and substituents led to (S)-8d [(S)-N-[2-(2,3-dihydro-6-methoxy-1H-inden-1-yl)ethyl]propionamide], which had high affinity for the human MT3 receptor (K-i = 0.041 nM) but no significant affinity for the hamster MT3 receptor (K-i = 3570 nM). In addition, a practical synthetic method of chiral N-[2-(2,3-dihydro-1H-inden-1-yl)ethyl]-alkanamides employing asymmetric hydrogenation with (S)-2,2'-bis(diphenylphosphino)-1,1'-binaphthyl-Ru has been established.

  DOI：

  10.1021/jm020114g
• 作为产物：
  描述：

  (3,4-dihydro-7-methoxy-1(2H)-naphthalenylidene)acetonitrile 在 钴 氨 、 氢气 作用下， 以 乙醇 为溶剂， 40.0 ℃ 、400.0 kPa 条件下， 生成 2-(3,4-dihydro-7-methoxy-1(2H)-naphthalenylidene)ethanamine
  参考文献：
  名称：

  Synthesis of a Novel Series of Benzocycloalkene Derivatives as Melatonin Receptor Agonists

  摘要：

  We synthesized a novel series of benzocycloalkene derivatives and evaluated their binding affinities to melatonin receptors. To control the spatial position of the amide group, one of the important pharmacophores, we incorporated an endo double bond, an exo double bond (E- and Z-configurations), and a chiral center (R- and S-configurations) at position 1. The indan derivatives with the S-configuration at position 1 were the most promising in terms of potency and selectivity for the human melatonin receptor (MT, site), while compounds with the R-configuration showed little potential. Our next attempt was to investigate the most favorable conformation of the methoxy group, the other important pharmacophore for binding to the MT, receptor. The introduction of a methyl group at position 5 of the indene ring conserved affinity; however, at position 7, it caused a decrease in affinity. These results suggested that the substitution at position 7 forced the methoxy group to adopt an unfavorable orientation. The optimization of the condensed ring size and substituents led to (S)-8d [(S)-N-[2-(2,3-dihydro-6-methoxy-1H-inden-1-yl)ethyl]propionamide], which had high affinity for the human MT3 receptor (K-i = 0.041 nM) but no significant affinity for the hamster MT3 receptor (K-i = 3570 nM). In addition, a practical synthetic method of chiral N-[2-(2,3-dihydro-1H-inden-1-yl)ethyl]-alkanamides employing asymmetric hydrogenation with (S)-2,2'-bis(diphenylphosphino)-1,1'-binaphthyl-Ru has been established.

  DOI：

  10.1021/jm020114g

文献信息

• Benzocycloalkene compounds, their production and use
  申请人：Takeda Chemical Industries, Ltd.

  公开号：US06235789B1

  公开（公告）日：2001-05-22

  A compound of the formula wherein R1 and R2 are H, a hydrocarbon group or a heterocyclic group, or R1 and R2 are combinedly a spiro ring; R3 is a hydrocarbon group, a substituted amino group, a substituted hydroxyl group or a heterocyclic group; R4 is H or alkyl; ring A is a substituted benzene ring; m and n denote 1 to 4; overscore (.........)} means a single or double bond or a salt, a process of producing thereof and a composition having a binding affinity for melatonin receptor.

  该化合物的公式为其中R1和R2是氢、烃基或杂环基，或者R1和R2共同形成螺环；R3是烃基、取代氨基、取代羟基或杂环基；R4是氢或烷基；环A是取代苯环；m和n表示1到4；overscore (.........)}表示单键或双键或盐，其制备方法以及具有与褪黑激素受体结合亲和力的组合物。
• BENZOCYCLOALKENE COMPOUNDS, THEIR PRODUCTION AND USE
  申请人：Takeda Chemical Industries, Ltd.

  公开号：EP0781271A1

  公开（公告）日：1997-07-02
• NEW PROCESS FOR THE PREPARATION OF N-[2-(7-METHOXY-1-NAPHTHYL)-ETHYL]ACETAMIDE
  申请人：GADOR S.A.

  公开号：EP2580183B1

  公开（公告）日：2014-07-23
• NEW PROCESS FOR THE PREPARATION OF N-[2-(7-METHOXY-1-NAPHTHYL)-ETHYL]ACETAMIDE AND NEW CRYSTALLINE FORM
  申请人：GADOR S.A.

  公开号：EP2580183A2

  公开（公告）日：2013-04-17
• US6235789B1
  申请人：——

  公开号：US6235789B1

  公开（公告）日：2001-05-22