2-(3,5-dibromo-2-methoxyphenyl)-1H-pyrrole | 10245-82-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯
• 英文名称: 2-(3,5-dibromo-2-methoxyphenyl)-1H-pyrrole
• 英文别名: 2-(3',5'-Dibrom-2'-methoxyphenyl)-1H-pyrrol；2-(3,5-Dibrom-2-methoxyphenyl)-1H-pyrrol；2-(2-methoxy-3,5-dibromophenyl)pyrrole；2-(3,5-dibromo-2-methoxy-phenyl)-pyrrole；2-(3,5-Dibrom-2-methoxy-phenyl)-pyrrol；2-(3,5-Dibrom-2-methoxyphenyl)-pyrrol
• CAS: 10245-82-6
• 化学式: C₁₁H₉Br₂NO
• 分子量: 331.007
• InChiKey: JLXGOYFXOKFPKJ-UHFFFAOYSA-N

物化性质

• 熔点：
  105 °C
• 沸点：
  366.9±37.0 °C(Predicted)
• 密度：
  1.747±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  15
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.09
• 拓扑面积：
  25
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  2-(3,5-dibromo-2-methoxyphenyl)-1H-pyrrole 在 pyridinium hydrobromide perbromide 作用下， 以 乙醇 为溶剂， 反应 0.17h， 以99%的产率得到2,3,4-tribromo-5-(3,5-dibromo-2-methoxyphenyl)-1H-pyrrole
  参考文献：
  名称：

  Laatsch, Hartmut; Pudleiner, Heinz, Liebigs Annalen der Chemie, 1989, p. 863 - 882

  摘要：

  DOI：
• 作为产物：
  描述：

  1-(3,5-Dibrom-2-methoxyphenyl)-3-(1,3-dioxan-2-yl)-1-propanon 在 盐酸 、 ammonium acetate 、 溶剂黄146 作用下， 以 水 、 溶剂黄146 为溶剂， 反应 144.17h， 生成 2-(3,5-dibromo-2-methoxyphenyl)-1H-pyrrole
  参考文献：
  名称：

  Laatsch, Hartmut; Pudleiner, Heinz, Liebigs Annalen der Chemie, 1989, p. 863 - 882

  摘要：

  DOI：

文献信息

• 5-(2-oxyphenyl)-pyrrole derivatives as dopamine D.sub.3 receptor
  申请人：SmithKline Beecham PLC

  公开号：US05523299A1

  公开（公告）日：1996-06-04

  Compounds of formula (I), ##STR1## wherein R.sup.1 represents C.sub.1-4 alkyl; and R.sup.2, R.sup.3, R.sup.4 and R.sup.5 each independently represent hydrogen, halogen, C.sub.1-4 alkyl, C.sub.1-4 alkoxy, C.sub.1-4 alkoxyC.sub.1-4 alkyl, C.sub.1-4 alkylsulphonyl, trifluoromethylsulphonyl; optionally substituted arylsulphonyl, optionally substituted heteroarylsulphonyl, optionally substituted aralkylsulphonyl, optionally substituted heteroaralkylsulphonyl, nitro, cyano, amino, mono- or di-alkylamino, trifluoromethyl, trifluoromethoxy, hydroxyl, hydroxyalkyl, C.sub.1-4 alkylthio, C.sub.1-4 alkanoyl, C.sub.1-4 alkoxycarbonyl, aminosulphonyl, alkylaminosulphonyl or dialkylaminosulphonyl; or R.sup.1 and R.sup.2 together form a linking chain-(CH.sub.2).sub.m Op (wherein m is 2 to 4 and p is zero or 1) which chain may be optionally substituted by one or two C.sub.1-4 alkyl groups; and Y represents a group selected from (a) or (b) wherein R.sup.6 and R.sup.7 independently represent hydrogen, C.sub.1-6 alkyl, optionally substituted arylC.sub.1-6 alkyl or optionally substituted heteroarylC.sub.1-6 alkyl; R.sup.8 represents C.sub.1-6 alkyl, C.sub.3-6 alkenyl or C.sub.3-6 cycloalkylC.sub.1-4 alkyl; and R.sup.9 represents C.sub.1-6 alkyl; C.sub.3-6 alkenyl; C.sub.3-6 cycloalkylC.sub.1-4 alkyl, optionally substituted arylC.sub.1-4 alkyl or optionally substituted heteroarylC.sub.1-4 alkyl; or NR.sup.8 R.sup.9 forms a heterocyclic ring (with the proviso that NR.sup.8 R.sup.9 is not piperazine); R.sup.10 represents C.sub.1-6 alkyl; C.sub.3-6 alkenyl; C.sub.3-6 cycloalkylC.sub.1-4 alkyl, optionally substituted arylC.sub.1-4 alkyl, or optionally substituted heteroarylC.sub.1-4 alkyl; and n is 1 to 3; and salts thereof, have affinity for dopamine D.sub.3 receptors and may be useful in the treatment of e.g., psychotic disorders.

  式(I)的化合物，其中R.sup.1代表C.sub.1-4烷基；而R.sup.2、R.sup.3、R.sup.4和R.sup.5分别独立地代表氢、卤素、C.sub.1-4烷基、C.sub.1-4烷氧基、C.sub.1-4烷氧基C.sub.1-4烷基、C.sub.1-4烷基磺酰基、三氟甲基磺酰基；可选择地取代的芳基磺酰基、可选择地取代的杂环芳基磺酰基、可选择地取代的芳基烷基磺酰基、可选择地取代的杂环烷基磺酰基、硝基、氰基、氨基、单烷基或双烷基氨基、三氟甲基、三
• Silver(I)-Catalyzed Route to Pyrroles: Synthesis of Halogenated Pseudilins as Allosteric Inhibitors for Myosin ATPase and X-ray Crystal Structures of the Protein-Inhibitor Complexes
  作者：René Martin、Célia Risacher、André Barthel、Anne Jäger、Arndt W. Schmidt、Sabine Richter、Markus Böhl、Matthias Preller、Krishna Chinthalapudi、Dietmar J. Manstein、Herwig O. Gutzeit、Hans-Joachim Knölker

  DOI：10.1002/ejoc.201402177

  日期：2014.7

  and pentachloropseudilin represent a new class of isoform-specific allosteric inhibitors of myosin ATPase. Herein, we describe an application of the silver(I)-catalyzed cycloisomerization of N-(homopropargyl)toluenesulfonamides to the total syntheses of these natural products and several non-natural analogues. Moreover, we examine the inhibitiory effect of pentahalogenated pseudilins on myosin ATPase

  五卤化 2-芳基吡咯型生物碱 pentabrompseudilin 和 pentachloropseudin 代表了一类新的肌球蛋白 ATP 酶的异构体特异性变构抑制剂。在此，我们描述了银 (I) 催化的 N-（高炔丙基）甲苯磺酰胺环异构化在这些天然产物和几种非天然类似物的全合成中的应用。此外，我们检查了五卤化假素对肌球蛋白 ATP 酶活性的抑制作用。
• Structure-Activity Relationships of Phenyl- and Benzoylpyrroles.
  作者：Hartmut LAATSCH、Bernd RENNEBERG、Ulf HANEFELD、Michael KELLNER、Heinz PUDLEINER、Gerhard HAMPRECHT、Hans-Peter KRAEMER、Heidrun ANKE

  DOI：10.1248/cpb.43.537

  日期：——

  Antitumor, antimicrobial, and phytotoxic activities of the marine antibiotic pentabromopseudilin (1a) and related phenyl-, benzyl- and benzoyl pyrroles were compared. All activities depended strongly on the substituent pattern, with the natural compound 1a being the most active one. As judged from model reactions, a covalent bond of nucleophiles to the pyrrole system may be involved in the inhibition

  比较了海洋抗生素五溴庚二素（1a）和相关的苯基，苄基和苯甲酰基吡咯的抗肿瘤，抗菌和植物毒性活性。所有活性在很大程度上取决于取代基的形式，其中天然化合物1a是最活跃的。从模型反应判断，亲核试剂与吡咯系统的共价键可能参与大分子合成的抑制。
• Phenyl, Pyrrolidin-2-yl substituted pyrroles having antipsychotic
  申请人：Duphar International Research B.V.

  公开号：US04791132A1

  公开（公告）日：1988-12-13

  The invention relates to a group of new phenyl, pyrrolidin-2-yl substituted 5-ring heterocyclic compounds of the formula ##STR1## wherein A is an unsaturated heterocyclic 5-ring having at least one nitrogen or oxygen atom in the ring, with the proviso that the phenyl substituent is in a meta-position with respect to the 2-pyrrolidinyl substituent. The compounds have interesting pharmacological, notably antipsychotic properties.

  本发明涉及一组新的苯基、吡咯烷-2-基取代的5元杂环化合物，其分子式为：##STR1## 其中，A是一种不饱和的5元杂环，其环中至少有一个氮或氧原子，且苯基取代基与2-吡咯烷基取代基的相对位置为间位。这些化合物具有有趣的药理学特性，尤其是抗精神病作用。
• Derivatives of phenyl, pyrrolidin-2-yl substituted 5-ring heterocycles having antipsychotic properties
  申请人：DUPHAR INTERNATIONAL RESEARCH B.V

  公开号：EP0259930A1

  公开（公告）日：1988-03-16

  The invention relates to a group of new phenyl, pyrrolidin-2-yl substituted 5-ring heterocyclic compounds of the formula wherein A is an unsaturated heterocylic 5-ring having at least one nitrogen or oxygen atom in the ring, with the proviso that the phenyl substituent is in a meta-position with respect to the 2-pyrrolidinyl substituent. The compounds have interesting pharmacological, notably antipsychotic properties.

  本发明涉及一组新的苯基、吡咯烷-2-基取代的 5 环杂环化合物，其式为 其中 A 是不饱和杂环 5-环，环中至少有一个氮原子或氧原子，但苯基取代基相对于 2-吡咯烷基取代基处于元位置。 这些化合物具有有趣的药理特性，尤其是抗精神病特性。