2-(3-methoxyphenylsulfanyl)ethylamine

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: 2-(3-methoxyphenylsulfanyl)ethylamine
• 英文别名: 2-(3-methoxyphenylthio)ethanamine；2-((3-Methoxyphenyl)thio)ethanamine；2-(3-methoxyphenyl)sulfanylethanamine
• 化学式: C₉H₁₃NOS
• 分子量: 183.274
• InChiKey: USPPRAOYKHROEO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  12
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  60.6
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2-(3-methoxyphenylsulfanyl)ethylamine 在 potassium carbonate 、 三氯氧磷 作用下， 以 乙腈 为溶剂， 反应 5.0h， 生成 8-methoxy-5-phenyl-2,3-dihydro-1,4-benzothiazepine
  参考文献：
  名称：

  Transformations of tetrahydro-1,4-benzoxazepines and tetrahydro-1,4-benzothiazepines under the action of alkynes. First example of the synthesis of tetrahydro-1,4-benzothiazonine-6-carboxylate

  摘要：

  It was shown that 2,3,4,5-tetrahydro-1,4-benzoxazepines were cleaved at the N-C(5) bond under the action of activated alkynes in methanol, forming o-(methoxyethyl)- and o-(methoxybenzyl)-phenyl(aminoethyl) ethers. The cleavage rate depended on the electronic effects of the substituents at the C-5 atom. Thiazepine ring expansion in tetrahydro-1,4-benzothiazepine was achieved for the first time via reaction with methyl propiolate to give a benzothiazonine.

  DOI：

  10.1007/s10593-013-1251-z
• 作为产物：
  描述：

  3-甲氧基苯硫酚 在 lithium aluminium tetrahydride 、 potassium carbonate 作用下， 以 乙醚 、 丙酮 为溶剂， 反应 36.0h， 生成 2-(3-methoxyphenylsulfanyl)ethylamine
  参考文献：
  名称：

  Transformations of tetrahydro-1,4-benzoxazepines and tetrahydro-1,4-benzothiazepines under the action of alkynes. First example of the synthesis of tetrahydro-1,4-benzothiazonine-6-carboxylate

  摘要：

  It was shown that 2,3,4,5-tetrahydro-1,4-benzoxazepines were cleaved at the N-C(5) bond under the action of activated alkynes in methanol, forming o-(methoxyethyl)- and o-(methoxybenzyl)-phenyl(aminoethyl) ethers. The cleavage rate depended on the electronic effects of the substituents at the C-5 atom. Thiazepine ring expansion in tetrahydro-1,4-benzothiazepine was achieved for the first time via reaction with methyl propiolate to give a benzothiazonine.

  DOI：

  10.1007/s10593-013-1251-z

文献信息

• PROCESS FOR PREPARING BENZOTHIAZEPINES FROM GAMMA-AMINOALKYLBENZENES
  申请人：Deng Shixian

  公开号：US20090227788A1

  公开（公告）日：2009-09-10

  The invention provides a process for preparing a 2,3,4,5-tetrahydro[1,4]benzothiazepine of formula: by reacting a [2-(acylaminoethyl)thio]arene of formula with an aldehyde or a multimer thereof, and with an acid. The invention also provides for first reacting the [2-(acylaminoethyl)thio]arene with the aldehyde or multimer thereof and a base to form an [N-hydroxymethyl-2-[acylaminoethyl)thio]arene of formula then treating the [N-hydroxymethyl-2-(acylaminoethyl)thio]arene with the acid to form the 2,3,4,5-tetrahydro[1,4]benzothiazepine.

  该发明提供了一种制备2,3,4,5-四氢[1,4]苯并噻吩的方法，通过将式中的[2-(酰胺基乙基)硫]芳烃与醛或其多聚物以及酸反应。该发明还提供了首先将[2-(酰胺基乙基)硫]芳烃与醛或其多聚物以及碱反应以形成式的[N-羟甲基-2-(酰胺基乙基)硫]芳烃，然后用酸处理[N-羟甲基-2-(酰胺基乙基)硫]芳烃以形成2,3,4,5-四氢[1,4]苯并噻吩。
• [EN] PROCESS FOR PREPARING BENZOTHIAZEPINES FROM GAMMA-AMINOALKYLBENZENES<br/>[FR] PROCÉDÉ POUR PRÉPARER DES BENZOTHIAZÉPINES À PARTIR DE GAMMA-AMINOALKYLBENZÈNES
  申请人：ARMGO PHARMA INC

  公开号：WO2009111463A1

  公开（公告）日：2009-09-11

  The invention provides a process for preparing a 2,3,4,5-tetrahydro[1,4]benzothiazepine of formula: [I] by reacting a [2-(acylaminoethyl)thio]arene of formula [II] with an aldehyde or a multimer thereof, and with an acid. The invention also provides for first reacting the [2-(acylaminoethyl)thio]arene with the aldehyde or multimer thereof and a base to form an [N-hydroxymethyl-2-[acylaminoethyl)thio]arene of formula [III]; then treating the [N-hydroxymethyl-2-(acylaminoethyl)thio]arene with the acid to form the 2,3,4,5-tetrahydro[1,4]benzothiazepine.

  本发明提供了一种制备式为[I]的2,3,4,5-四氢[1,4]苯并噻吩的方法，该方法通过将式[II]的[2-(酰胺基乙基)硫]芳烃与醛或其多聚物以及酸反应而得到。本发明还提供首先将[2-(酰胺基乙基)硫]芳烃与醛或其多聚物以及碱反应以形成式[III]的[N-羟甲基-2-(酰胺基乙基)硫]芳烃；然后用酸处理[N-羟甲基-2-(酰胺基乙基)硫]芳烃以形成2,3,4,5-四氢[1,4]苯并噻吩。
• Process for preparing benzothiazepines from gamma-aminoalkylbenzenes
  申请人：Deng Shixian

  公开号：US08618282B2

  公开（公告）日：2013-12-31

  The invention provides a process for preparing a 2,3,4,5-tetrahydro[1,4]benzothiazepine of formula: by reacting a [2-(acylaminoethyl)thio]arene of formula with an aldehyde or a multimer thereof, and with an acid. The invention also provides for first reacting the [2-(acylaminoethyl)thio]arene with the aldehyde or multimer thereof and a base to form an [N-hydroxymethyl-2-[acylaminoethyl)thio]arene of formula then treating the [N-hydroxymethyl-2-(acylaminoethyl)thio]arene with the acid to form the 2,3,4,5-tetrahydro[1,4]benzothiazepine.

  本发明提供了一种制备式为2,3,4,5-四氢[1,4]苯并噻吩的方法，该方法通过将式为[2-(酰胺基乙基)硫代]芳烃与醛或其多聚物以及酸反应来实现。本发明还提供了一种先将[2-(酰胺基乙基)硫代]芳烃与醛或其多聚物和碱反应以形成式为[N-羟甲基-2-(酰胺基乙基)硫代]芳烃，然后用酸处理[N-羟甲基-2-(酰胺基乙基)硫代]芳烃以形成2,3,4,5-四氢[1,4]苯并噻吩。
• COMPOUNDS FOR TREATING DISORDERS SENSITIVE TO SEROTONINERGIC REGULATION CONTROLLED BY THE 5-HT1A RECEPTORS
  申请人：Neurolixis

  公开号：EP3260452A1

  公开（公告）日：2017-12-27

  The invention concerns compounds that possess a high affinity at 5-HT1A receptors and an agonist efficacy, as measured by Emax values from a cellular activation assay, that is higher than that of the compounds described in prior art. The capacity of the compounds of the invention to activate an effector protein complex is higher than that the most efficacious agonist described in prior art. Compounds of the invention also exhibit an exceptionally high selectivity (Ki ratio greater than 1000-fold) with respect, in particular, to dopamine D2 receptors and adrenergic receptors of the alpha1 subtype. This selectivity which constitutes a great advantage since it means that the compounds will avoid inducing (central and peripheral) effects associated with activating or inhibiting such receptors

  本发明所涉及的化合物对 5-HT1A 受体具有高亲和力，并且根据细胞活化实验的 Emax 值衡量，其激动剂功效高于现有技术中所述的化合物。本发明化合物激活效应蛋白复合物的能力高于现有技术中最有效的激动剂。本发明的化合物还具有极高的选择性（Ki 比值大于 1000 倍），特别是对多巴胺 D2 受体和α1 亚型肾上腺素能受体。这种选择性具有很大的优势，因为它意味着本发明化合物可以避免引起与激活或抑制这些受体相关的（中枢和外周）效应。
• Compounds for treating disorders sensitive to serotoninergic regulation controlled by the 5-HT1A receptors
  申请人：NEUROLIXIS

  公开号：US10562853B2

  公开（公告）日：2020-02-18

  The invention concerns compounds that possess a high affinity at 5-HT1A receptors and an agonist efficacy, as measured by Emax values from a cellular activation assay, that is higher than that of the compounds described in prior art. The capacity of the compounds of the invention to activate an effector protein complex is higher than that the most efficacious agonist described in prior art. Compounds of the invention also exhibit an exceptionally high selectivity (Ki ratio greater than 1000-fold) with respect, in particular, to dopamine D2 receptors and adrenergic receptors of the alpha1 subtype. This selectivity which constitutes a great advantage since it means that the compounds will avoid inducing (central and peripheral) effects associated with activating or inhibiting such receptors.

  本发明所涉及的化合物对 5-HT1A 受体具有高亲和力，并且根据细胞活化实验的 Emax 值衡量，其激动剂功效高于现有技术中所述的化合物。本发明化合物激活效应蛋白复合物的能力高于现有技术中最有效的激动剂。本发明的化合物还具有极高的选择性（Ki 比值大于 1000 倍），特别是对多巴胺 D2 受体和α1 亚型肾上腺素能受体。这种选择性具有很大的优势，因为它意味着本发明的化合物可以避免引起与激活或抑制这些受体相关的（中枢和外周）效应。