(Z)-2-(β-bromovinyl)quinoline | 218902-64-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 喹啉及其衍生物
• 英文名称: (Z)-2-(β-bromovinyl)quinoline
• 英文别名: (Z)-2-(2-Bromovinyl)quinoline；2-[(Z)-2-bromoethenyl]quinoline
• CAS: 218902-64-8
• 化学式: C₁₁H₈BrN
• 分子量: 234.095
• InChiKey: KRKTYQUSRQFVQW-FPLPWBNLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  13
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  12.9
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  (Z)-2-(β-bromovinyl)quinoline 在 bis-triphenylphosphine-palladium(II) chloride 、 copper(l) iodide 甲醇 、 potassium carbonate 、 三乙胺 作用下， 生成 (Z)-2-(but-1-en-3-ynyl)quinoline
  参考文献：
  名称：

  （Z）-聚芳族和杂芳族乙烯基乙炔的实用合成。

  摘要：

  [反应：seet text]描述了到几种（Z）-聚芳族和杂芳族取代的乙烯基乙炔的两种合成路线。用作原料的芳基或杂芳基取代的甲醛的性质决定了所用维蒂希盐的选择。构造聚芳族和含吡啶的烯炔的一种非常有吸引力的方法是在叔丁醇钾存在下，聚芳族和含吡啶的醛与溴甲基三苯基溴化phosph的反应，然后进行Sonogashira甲硅烷基化反应（方法B）。

  DOI：

  10.1021/ol0508173
• 作为产物：
  描述：

  1,1-二溴-2-(2-喹啉基)-1-乙烯 在 palladium diacetate 、 三正丁基氢锡 、 三苯基膦 作用下， 以 甲苯 为溶剂， 反应 0.3h， 以65%的产率得到(Z)-2-(β-bromovinyl)quinoline
  参考文献：
  名称：

  Stereoselective Hydrogenolysis of 1,1-Dibromo-1-alkenes and Stereospecific Synthesis of Conjugated (Z)-Alkenyl Compounds

  摘要：

  The Pd-catalyzed hydrogenolysis of 1,1-dibromoalkenes with Bu3SnH occurs at room temperature stereoselectively to give (Z)-1-bromo-1-alkenes. We sought to determine the optimal reaction conditions and illustrate the scope of this method with 32 dibromoalkenes including alkenyl- and alkynyl-conjugated 1,l-dibromo-l-alkenes 7a-h and 2,2-disubstituted I,1-dibromo-1-alkenes 9a-f. Triphenylphosphine was the best ligand for the Pd-catalyzed hydrogenolysis. A wide range of solvents can be used for this reaction excluding EtOH, AcOH, and CHCl3. However, the reaction proceeds even in these solvents with the addition of a cosolvent or radical scavenger. The reaction of 1,1-diiodo-1-alkene (3) gave a mixture of (Z)-1-iodo-1-alkene (4), (Z)-1-tributylstannyl-1-alkene (5), and a terminal alkene 6, while that of 1,1-dichloroalkene did not occur. This selectivity can be explained by the stereoselective insertion of Pd(0) to a trans bromine-alkenyl carbon bond, successive transmetalation with Bu3SnH, and reductive elimination. The Suzuki and Sonogashira couplings of the resulting (Z)-1-bromo-1-alkenes with alkenyl(dialkoxy)borane and terminal alkyne occurred to give conjugated polyenes and enynes stereospecifically. The Pd-catalyzed hydrogenolysis of 1,l-dibromo-l-alkene and successive cross-coupling can be carried out either in a stepwise manner or in one-pot under the same Pd catalysis. These two processes should be useful for the synthesis of geometrically pure polyene and enyne with a Z-alkenyl unit.

  DOI：

  10.1021/jo9812781

文献信息

• NOVEL INHIBITOR COMPOUNDS OF PHOSPHODIESTERASE TYPE 10A
  申请人：Abbott GmbH & Co. KG

  公开号：US20130116233A1

  公开（公告）日：2013-05-09

  The present invention relates to novel compounds of the formula I which are inhibitors of phosphodiesterase type 10A and to their use for the manufacture of a medicament and which thus are suitable for treating or controlling of medical disorders selected from neurological disorders and psychiatric disorders, for ameliorating the symptoms associated with such disorders and for reducing the risk of such disorders.

  本发明涉及一种新型化合物，其化学式为I，它们是磷酸二酯酶10A的抑制剂，并且用于制备药物，因此适用于治疗或控制从神经系统疾病和精神疾病中选择的医学疾病，改善与这些疾病相关的症状，并减少这些疾病的风险。
• Method for the synthesis of 3-substituted indolizine and benzoindolizine compounds
  申请人：Hayford Anthony

  公开号：US20060160770A1

  公开（公告）日：2006-07-20

  A method of making a compound of Formula I: comprises reacting a compound of Formula II with a compound such as R 1 OH or R 1 SH, to produce said compound of Formula I. Compounds of Formula I are useful, among other things, as dyes, spectral sensitizers, glycosidase inhibitors, and as antibacterial, antiviral, and anti-inflammatory agents.

  制备Formula I化合物的方法包括将Formula II化合物与诸如R1OH或R1SH的化合物反应，从而产生所述Formula I化合物。Formula I化合物可用作某些染料、光谱增敏剂、糖苷酶抑制剂以及抗菌、抗病毒和抗炎剂。
• Direct Synthesis of Monofunctionalized Indolizine Derivatives Bearing Alkoxymethyl Substituents at C-3 and Their Benzofused Analogues
  作者：Joseph Kaloko、Anthony Hayford

  DOI：10.1021/ol051860t

  日期：2005.9.1

  inorganic base (KOH, K2CO3, CsF, or KF) serendipitously gave 3-alkoxylmethylindolizines and the corresponding 1-alkoxymethylpyrrolo [1,2-a]quinolines and not the anticipated desilylated vinylacetylene derivatives. A mechanistic possibility for this unexpected chemical transformation is suggested.

  [反应：见正文]在适当的无机碱（KOH，K2CO3，CsF或KF）存在下，用几种醇在回流下处理（Z）-2-吡啶和喹啉甲硅烷基化的乙烯基乙炔，偶然产生了3-烷氧基甲基吲哚并相应的化合物。 1-烷氧基甲基吡咯并[1,2-a]喹啉，而不是预期的去甲硅烷基乙炔衍生物。建议这种意外的化学转化的机械可能性。
• Substituted isoquinolines and phthalazines as inhibitors of phosphodiesterase type 10A
  申请人：Abbott GmbH & Co. KG

  公开号：US09273068B2

  公开（公告）日：2016-03-01

  The present invention relates to novel compounds of the formula (I), wherein Het, A, Q, X1, X2, X3, R1 and R2 are defined in the specification, which are inhibitors of phosphodiesterase type 10A and to their use for the manufacture of a medicament and which thus are suitable for treating or controlling of medical disorders selected from neurological disorders and psychiatric disorders, for ameliorating the symptoms associated with such disorders and for reducing the risk of such disorders.

  本发明涉及公式（I）的新化合物，其中Het，A，Q，X1，X2，X3，R1和R2在规范中有定义，它们是磷酸二酯酶10A的抑制剂，并且用于制造药物，因此适用于治疗或控制选择的医学疾病，包括神经系统疾病和精神障碍，改善与此类疾病相关的症状，并降低此类疾病的风险。
• INHIBITORS OF PHOSPHODIESTERASE TYPE 10A
  申请人：AbbVie Deutschland GmbH & Co KG

  公开号：EP2776418B1

  公开（公告）日：2017-01-04