4-bromo-5-(2,2-dimethoxyethyl)thiophene-2-carbaldehyde | 1093379-43-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 噻吩类
• 英文名称: 4-bromo-5-(2,2-dimethoxyethyl)thiophene-2-carbaldehyde
• 英文别名: 4-bromo-5-(2,2-dimethoxyethyl)thiophen-2-carbaldehyde
• CAS: 1093379-43-1
• 化学式: C₉H₁₁BrO₃S
• 分子量: 279.155
• InChiKey: UFWLHZFWVGTSEG-UHFFFAOYSA-N

物化性质

• 沸点：
  317.9±42.0 °C(Predicted)
• 密度：
  1.503±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  14
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.44
• 拓扑面积：
  63.8
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  4-bromo-5-(2,2-dimethoxyethyl)thiophene-2-carbaldehyde 在 吡啶 、 盐酸 、 苯酐 、 正丁基锂 、 硫酸 、 盐酸羟胺 、 对甲苯磺酸 、 原甲酸三甲酯 作用下， 以 四氢呋喃 、 吡啶 、 甲醇 、 正己烷 、 水 、 乙腈 为溶剂， 反应 29.75h， 生成 methyl 1-benzyl-6'-methoxy-6',7'-dihydrospiro[piperidine-4,4'-thieno[3,2-c]pyran]-2'-carboxylate
  参考文献：
  名称：

  Thiophene Bioisosteres of Spirocyclic σ Receptor Ligands: Relationships between Substitution Pattern and σ Receptor Affinity

  摘要：

  On the basis of the 6',7'-dihydrospiro-[piperidine-4,4'-thieno[3,2-c]pyran] framework, a series of more than 30 sigma ligands with versatile substituents in 1-, 2'-, and 6'-position has been synthesized and pharmacologically evaluated in order to find novel structure-affinity relationships. It was found that a cyclohexylmethyl residue at the piperidine N-atom instead of a benzyl moiety led to increased sigma(2) affinity and therefore to decreased sigma(1)/sigma(2), selectivity. Small substituents (e.g., OH, OCH3, CN, CH2OH) in 6'-position adjacent to the O-atom were well tolerated by the sigma(1) receptor. Removal of the substituent in 6'-position resulted in very potent but unselective a ligands (13). A broad range of substituents with various lipophilic and H-bond forming properties was introduced in 2'-position adjacent to the S-atom without loss of a, affinity. However, very polar and basic substituents in both 2'- and 6'-position decreased the a, affinity considerably. It is postulated that the electron density of the thiophene moiety has a big impact on the sigma(1) affinity.

  DOI：

  10.1021/jm300302p
• 作为产物：
  描述：

  (E/Z)-3-bromo-2-(2-methoxyvinyl)thiophene 在 对甲苯磺酸 lithium diisopropyl amide 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 反应 24.67h， 生成 4-bromo-5-(2,2-dimethoxyethyl)thiophene-2-carbaldehyde
  参考文献：
  名称：

  WO2008/155132

  摘要：

  公开号：

文献信息

• SPIRO ÝPIPERIDINE-4, 4' -THIENO Ý3, 2-C¨PYRAN¨DERIVATIVES AND RELATED COMPOUNDS AS INHIBITORS OF THE SIGMA RECEPTOR FOR THE TREATMENT OF PSYCHOSIS
  申请人：Laboratorios Del. Dr. Esteve, S.A.

  公开号：EP2170903A1

  公开（公告）日：2010-04-07
• SPIRO[PIPERIDINE-4,4' -THIENO[3, 2-C]PYRAN]DERIVATIVES AND RELATED COMPOUNDS AS INHIBITORS OF THE SIGMA RECEPTOR FOR THE TREATMENT OF PSYCHOSIS
  申请人：Laboratorios del. Dr. Esteve, S.A.

  公开号：EP2170903B1

  公开（公告）日：2012-09-05
• SPIRO [PIPERIDINE-4- 4' -THIENO [3,2-C] PYRAN] DERIVATIVES AND RELATED COMPOUNDS AS INHIBITORS OF THE SIGMA RECEPTOR FOR THE TREATMENT OF PSYCHOSIS
  申请人：Oberdorf Christoph

  公开号：US20100190813A1

  公开（公告）日：2010-07-29

  The present invention relates to compounds having pharmacological activity towards the sigma (σ) receptor, and more particularly to some thieno-pyrano-pyrazole derivatives, to processes of preparation of such compounds, to pharmaceutical compositions comprising them, and to their use in therapy and prophylaxis, in particular for the treatment of psychosis or pain.
• [EN] SPIRO [PIPERIDINE-4, 4' -THIENO [3, 2-C] PYRAN] DERIVATIVES AND RELATED COMPOUNDS AS INHIBITORS OF THE SIGMA RECEPTOR FOR THE TREATMENT OF PSYCHOSIS<br/>[FR] DÉRIVÉS DE SPIRO[PIPERIDIN-4,4'-THIENO[3,2-C]PYRAN] ET COMPOSÉS ASSOCIÉS UTILISÉS COMME INHIBITEURS DU RÉCEPTEUR SIGMA POUR LE TRAITEMENT DE LA PSYCHOSE
  申请人：ESTEVE LABOR DR

  公开号：WO2008155132A1

  公开（公告）日：2008-12-24

  [EN] The present invention relates to compounds having pharmacological activity towards the sigma (s) receptor, and more particularly to some thieno-pyrano-pyrazole derivatives, to processes of preparation of such compounds, to pharmaceutical compositions comprising them, and to their use in therapy and prophylaxis, in particular for the treatment of psychosis or pain.
  [FR] La présente invention concerne des composés ayant une activité pharmacologique vis-à-vis du récepteur sigma (s), et plus particulièrement quelques dérivés de thiéno-pyrano-pyrazole, des procédés de préparation de ces composés, des compositions pharmaceutiques les comprenant, et leur utilisation en thérapie et en prophylaxie, en particulier pour le traitement de la psychose ou de la douleur.
• WO2008/155132
  申请人：——

  公开号：——

  公开（公告）日：——