[1-(2-bromophenyl)but-3-ynyloxy](tert-butyl)dimethylsilane | 1258636-22-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: [1-(2-bromophenyl)but-3-ynyloxy](tert-butyl)dimethylsilane
• 英文别名: 4-(2-bromophenyl)-4-tert-butyldimethylsilyloxybut-1-yne；1-(2-Bromophenyl)but-3-ynoxy-tert-butyl-dimethylsilane
• CAS: 1258636-22-4
• 化学式: C₁₆H₂₃BrOSi
• 分子量: 339.348
• InChiKey: SUDGFLJUMKFEBD-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.54
• 重原子数：
  19
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  9.2
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  [1-(2-bromophenyl)but-3-ynyloxy](tert-butyl)dimethylsilane 在 tris-(dibenzylideneacetone)dipalladium(0) 、 正丁基锂 、 四溴化碳 、 dicyclohexyl(2',4',6'-triisopropyl-[1,1'-biphenyl]-3-yl)phosphine 、 sodium hexamethyldisilazane 、 sodium hydride 、 二异丙胺 、 三苯基膦 作用下， 以 四氢呋喃 、 正己烷 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 14.5h， 生成 dimethyl 5-((tert-butyldimethylsilyl)oxy)-1,2,4,5-tetrahydro-3H-cyclopenta[a]naphthalene-3,3-dicarboxylate
  参考文献：
  名称：

  Synthesis of 1,2-Disubstituted Cyclopentenes by Palladium-Catalyzed Reaction of Homopropargyl-Substituted Dicarbonyl Compounds with Organic Halides via 5-Endo-Dig Cyclization

  摘要：

  Palladium catalysts with bulky biaryl phosphine ligands allow homopropargyl-substituted dicarbonyl compounds to undergo intramolecular addition via a rare 5-endo-dig pathway. C-C bond forming reductive elimination follows the addition to Introduce alkenyl and alkynyl as well as aryl groups by using the corresponding organic halides. The cyclization is versatile enough to be applicable to the synthesis of highly substituted dihydropyrrole and a fused tricyclic compound.

  DOI：

  10.1021/ol301257m
• 作为产物：
  描述：

  邻溴苯甲醛 在 咪唑 、 正丁基锂 作用下， 以 四氢呋喃 、 正己烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 3.5h， 生成 [1-(2-bromophenyl)but-3-ynyloxy](tert-butyl)dimethylsilane
  参考文献：
  名称：

  Synthesis of 1,2-Disubstituted Cyclopentenes by Palladium-Catalyzed Reaction of Homopropargyl-Substituted Dicarbonyl Compounds with Organic Halides via 5-Endo-Dig Cyclization

  摘要：

  Palladium catalysts with bulky biaryl phosphine ligands allow homopropargyl-substituted dicarbonyl compounds to undergo intramolecular addition via a rare 5-endo-dig pathway. C-C bond forming reductive elimination follows the addition to Introduce alkenyl and alkynyl as well as aryl groups by using the corresponding organic halides. The cyclization is versatile enough to be applicable to the synthesis of highly substituted dihydropyrrole and a fused tricyclic compound.

  DOI：

  10.1021/ol301257m

文献信息

• Sequential Sonogashira/Carbopalladative Cyclization/Suzuki Reactions Catalyzed by a Single Palladium Source by Using Protected Homopropargyl Alcohol
  作者：Xin Wang、Lingyan Liu、Weixing Chang、Jing Li

  DOI：10.1002/ejoc.201000515

  日期：——

  A novel cascade combination reaction catalyzed by a single palladium source for the synthesis of various indene derivatives is reported. The approach involved sequential Sonogashira/carbopalladative cyclization/Suzuki coupling reactions by using three readily available components, such as homopropargyl alcohol, aryl iodides or aryl bromides, and arylboronic acids. The overall domino reaction yields

  报道了一种由单一钯源催化的用于合成各种茚衍生物的新型级联组合反应。该方法涉及通过使用三种容易获得的组分（例如高炔丙醇、芳基碘化物或芳基溴化物和芳基硼​​酸）进行顺序 Sonogashira/碳钯环化/铃木偶联反应。多米诺骨牌反应的总产率高达 70%。