3-methyl-4-(2-thienyl)tetrahydro-2H-thiopyran-4-ol | 217301-92-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 噻烷
• 英文名称: 3-methyl-4-(2-thienyl)tetrahydro-2H-thiopyran-4-ol
• 英文别名: 3-Methyl-4-thiophen-2-ylthian-4-ol
• CAS: 217301-92-3
• 化学式: C₁₀H₁₄OS₂
• 分子量: 214.353
• InChiKey: CPIFMUWUCKBYNS-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  13
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.6
• 拓扑面积：
  73.8
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  3-methyl-4-(2-thienyl)tetrahydro-2H-thiopyran-4-ol 在 lithium aluminium tetrahydride 、 sodium azide 、 potassium carbonate 、 三氯乙酸 作用下， 以 四氢呋喃 、 六甲基磷酰三胺 、 氯仿 为溶剂， 反应 144.0h， 生成 trans-1-<3-methyl-4-(2-thienyl)tetrahydro-2H-thiopyran-4-yl>piperidine
  参考文献：
  名称：

  The search for TCP analogues binding to the low affinity PCP receptor sites in the rat cerebellum

  摘要：

  With the aim of obtaining selective ligands of the low affinity binding sites of [H-3]-1-[1-(2-thienyl) cyclohexyl] piperidine ([H-3]TCP) in the rat cerebellum, oxygen and sulfur atoms were introduced in the TCP structure and derivatives to obtain analogues with a lowered lipophilicity. These compounds, and others already obtained, were assayed comparatively to determine their affinities for three sites labeled with [H-3]TCP: one in the forebrain, the originally described PCP receptor, and two in the rat cerebellum. Lowering the Lipophilicity and modifying the hetero-aromatic moiety yielded some Ligands with increased affinity for the low affinity sites in the rat cerebellum and decreased affinity for the high affinity sites in the forebrain. Particularly, two compounds displaying both a high affinity and a good selectivity might be valuable tools to elucidate the pharmacology of the low affinity PCP sites labeled with [H-3]TCP in the rat cerebellum. (C) Elsevier, Paris.

  DOI：

  10.1016/s0223-5234(99)80046-4
• 作为产物：
  描述：

  3-methyltetrahydro-4H-thiopyran-4-one 、 magnesium,2H-thiophen-2-ide,bromide 以 乙醚 为溶剂， 反应 16.0h， 以98%的产率得到3-methyl-4-(2-thienyl)tetrahydro-2H-thiopyran-4-ol
  参考文献：
  名称：

  The search for TCP analogues binding to the low affinity PCP receptor sites in the rat cerebellum

  摘要：

  With the aim of obtaining selective ligands of the low affinity binding sites of [H-3]-1-[1-(2-thienyl) cyclohexyl] piperidine ([H-3]TCP) in the rat cerebellum, oxygen and sulfur atoms were introduced in the TCP structure and derivatives to obtain analogues with a lowered lipophilicity. These compounds, and others already obtained, were assayed comparatively to determine their affinities for three sites labeled with [H-3]TCP: one in the forebrain, the originally described PCP receptor, and two in the rat cerebellum. Lowering the Lipophilicity and modifying the hetero-aromatic moiety yielded some Ligands with increased affinity for the low affinity sites in the rat cerebellum and decreased affinity for the high affinity sites in the forebrain. Particularly, two compounds displaying both a high affinity and a good selectivity might be valuable tools to elucidate the pharmacology of the low affinity PCP sites labeled with [H-3]TCP in the rat cerebellum. (C) Elsevier, Paris.

  DOI：

  10.1016/s0223-5234(99)80046-4

文献信息

• NOUVEAUX DERIVES DE PHENCYCLIDINES, DES PROCEDES POUR LEUR PREPARATION ET DES COMPOSITIONS PHARMACEUTIQUES LES CONTENANT
  申请人：SOCIETE DE CONSEILS DE RECHERCHESET D'APPLICATIONS SCIENTIFIQUES (S.C.R.A.S.)

  公开号：EP0986555A1

  公开（公告）日：2000-03-22
• US6342511B1
  申请人：——

  公开号：US6342511B1

  公开（公告）日：2002-01-29
• [EN] NOVEL PHENCYCLIDINE DERIVATIVES, PREPARATION METHODS AND PHARMACEUTICAL COMPOSITIONS CONTAINING SAME<br/>[FR] NOUVEAUX DERIVES DE PHENCYCLIDINES, DES PROCEDES POUR LEUR PREPARATION ET DES COMPOSITIONS PHARMACEUTIQUES LES CONTENANT
  申请人：SOCIETE DE CONSEILS DE RECHERCHES ET D'APPLICATIONS SCIENTIFIQUES (S.C.R.A.S.)

  公开号：WO1998055478A1

  公开（公告）日：1998-12-10

  (EN) The invention concerns novel phenycyclidine derivatives with selective affinity for low affinity receptors, methods for preparing them, pharmaceutical compositions containing them and their use as protective agents for central or peripheral nervous system cells against acute or chronic degeneration, or as anticonvulsant.(FR) La présente invention concerne de nouveaux dérivés de phencyclidines possédant une affinité sélective pour les récepteurs de basse affinité, des procédés pour leur préparation, des compositions pharmaceutiques les contenant et leur utilisation notamment en tant qu'agent protecteur des cellules du système nerveux central ou périphérique contre les dégénérescences aiguës ou chroniques, ou comme agent anticonvulsivant.
• The search for TCP analogues binding to the low affinity PCP receptor sites in the rat cerebellum
  作者：Jacques Hamon、Florence Espaze、Jacques Vignon、Jean-Marc Kamenka

  DOI：10.1016/s0223-5234(99)80046-4

  日期：1999.2

  With the aim of obtaining selective ligands of the low affinity binding sites of [H-3]-1-[1-(2-thienyl) cyclohexyl] piperidine ([H-3]TCP) in the rat cerebellum, oxygen and sulfur atoms were introduced in the TCP structure and derivatives to obtain analogues with a lowered lipophilicity. These compounds, and others already obtained, were assayed comparatively to determine their affinities for three sites labeled with [H-3]TCP: one in the forebrain, the originally described PCP receptor, and two in the rat cerebellum. Lowering the Lipophilicity and modifying the hetero-aromatic moiety yielded some Ligands with increased affinity for the low affinity sites in the rat cerebellum and decreased affinity for the high affinity sites in the forebrain. Particularly, two compounds displaying both a high affinity and a good selectivity might be valuable tools to elucidate the pharmacology of the low affinity PCP sites labeled with [H-3]TCP in the rat cerebellum. (C) Elsevier, Paris.