(Z)-1-(β-bromovinyl)naphthalene | 77150-84-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: (Z)-1-(β-bromovinyl)naphthalene
• 英文别名: (Z)-1-(2-bromovinyl)naphthalene；(Z)-1-(bromovinyl)naphthalene；1-(2-bromo-vinyl)-naphthalene；1-(2-Brom-vinyl)-naphthalin；1-[(Z)-2-bromoethenyl]naphthalene
• CAS: 77150-84-6
• 化学式: C₁₂H₉Br
• 分子量: 233.107
• InChiKey: CCWARAMLMHCSOW-HJWRWDBZSA-N

物化性质

• 沸点：
  336.0±11.0 °C(Predicted)
• 密度：
  1.446±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.6
• 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：
  0
• 氢给体数：
  0
• 氢受体数：
  0

反应信息

• 作为反应物：
  描述：

  (Z)-1-(β-bromovinyl)naphthalene 在 二苯甲酮 、 乙醚 、 苯基锂 作用下， 生成 1-chloro-1-[1]naphthyl-3,3-diphenyl-allene
  参考文献：
  名称：

  Bertin, Annales de Chimie (Cachan, France), 1953, vol. <12> 8, p. 296,325

  摘要：

  DOI：
• 作为产物：
  描述：

  1,1-二溴-2-(1-萘基)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 0.1h， 以87%的产率得到(Z)-1-(β-bromovinyl)naphthalene
  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

• A Convenient Stereoselective Reduction of <i>Gem</i>-Dibromides with a Combination of Dimethyl Phosphite and Potassium Carbonate
  作者：Yalei Zhao、Tieqiao Chen、Xiang-Bo Wang、Li-Biao Han

  DOI：10.1080/10426507.2015.1024786

  日期：2015.11.2

  GRAPHICAL ABSTRACT Abstract An efficient and highly stereoselective reduction of a gem-dibromocyclopropane to the corresponding monobromocyclopropane under mild reaction conditions was developed using a combination of dimethyl phosphite and potassium carbonate. This reaction provided a simple and practical way for the synthesis of the valuable monobromocyclopropanes and β-monobromoalkenes.

  图形摘要摘要使用亚磷酸二甲酯和碳酸钾的组合，在温和的反应条件下，开发了一种高效且高度立体选择性地将嵴二溴环丙烷还原为相应的单溴环丙烷。该反应为合成有价值的单溴环丙烷和β-单溴烯烃提供了一种简单实用的方法。
• Ohmic Heating and Ionic Liquids in Combination for the Indium-Promoted Synthesis of 1-Halo Alkenyl Compounds: Applications to Pd-Catalysed Cross-Coupling Reactions
  作者：Raquel G. Soengas、Vera L. M. Silva、Joana Pinto、Humberto Rodríguez-Solla、Artur M. S. Silva

  DOI：10.1002/ejoc.201501162

  日期：2016.1

  We have explored the combination of ohmic heating (ΩH) with ionic liquids for indium-promoted reactions and report herein the indium-promoted dehalogenation of gem-dibromo alkenes and the indium-mediated reductive elimination of chlorohydrins for the synthesis of 1-halo alkenyl derivatives. Heck, Stille, Suzuki, Kumada and Sonogashira couplings of the resulting 1-halo-1-alkenes with appropriate reagents

  我们已经探索了欧姆加热 (ΩH) 与离子液体的结合用于铟促进反应，并在此报告了铟促进的二溴烯烃脱卤和铟介导的氯醇还原消除用于合成 1-卤代烯基衍生物. Heck、Stille、Suzuki、Kumada 和 Sonogashira 将得到的 1-halo-1-烯烃与合适的试剂偶联，得到烯烃、二烯和烯炔。
• Metal-Mediated Debromination of gem-Dibromoalkenes under Mild Conditions
  作者：Raquel Soengas、Artur Silva、Humberto Rodríguez-Solla

  DOI：10.1055/s-0035-1561558

  日期：——

  We describe the facile and efficient metal-promoted reduction of C–Br bonds of gem -dibromides. When the reaction is mediated by indium, the corresponding vinyl bromides are obtained in good yields and high E -stereoselectivities. Alternatively, when the reduction is mediated by samarium diiodide, vinyl bromides are obtained in moderate yields and good Z -selectivities.

  我们描述了宝石二溴化物的 C-Br 键的简单有效的金属促进还原。当反应由铟介导时，以良好的收率和高 E 立体选择性获得相应的乙烯基溴。或者，当还原由二碘化钐介导时，乙烯基溴以中等产率和良好的 Z 选择性获得。
• C-H Bond Activation: A Versatile Protocol for the Direct Arylation and Alkenylation of Oxazoles
  作者：Sandrine Piguel、François Besselièvre、Sabrina Lebrequier、Florence Mahuteau-Betzer

  DOI：10.1055/s-0029-1216987

  日期：2009.10

  The versatile palladium complex Pd(PPh3)4 catalyses both direct arylation and alkenylation of oxazoles efficiently. The method is regioselective and stereospecific with respect to bromoalkenes and tolerates a wide range of functional groups.

  多功能的钯配合物Pd(PPh3)4能够高效催化噁唑的直接芳基化和烯基化反应。该方法具有区域选择性和立体专一性，适用于溴代烯烃，并对多种官能团具有耐受性。
• A new synthesis of π-electron conjugated phosphonates and phosphonic bis(diethylamides) and their SHG activities
  作者：Takuji Ogawa、Naoya Usuki、Noboru Ono

  DOI：10.1039/a709082j

  日期：——

  A series of vinylic and arylic phosphonates and phosphonic bis(diethylamides) were prepared by copper promoted substitution of the corresponding bromides. These π-electron conjugated phosphonates and phosphonic bis(diethylamides) were investigated to elucidate their optical and second harmonic generation (SHG) properties; it was found that diphenyl 2-(4-dimethylaminophenyl)ethenylphosphonate exhibited strong SHG activity, the efficiency being 13 times greater than that of urea.

  通过铜催化的相应溴化物的取代反应，制备了一系列乙烯基和芳基膦酸盐及双（二乙基酰胺）膦酸。研究了这些共轭的磷酸盐和双（二乙基酰胺）膦酸的光学性质和二次谐波产生（SHG）特性；发现二苯基2-（4-二甲氨基苯基）乙烯基膦酸盐具有强烈的SHG活性，效率比尿素高13倍。