(Z)-(5-bromopent-3-en-1-yn-1-yl)benzene | 568571-18-6

• 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: (Z)-(5-bromopent-3-en-1-yn-1-yl)benzene
• 英文别名: (Z)-1-bromo-5-phenylpent-2-en-4-yne；[(Z)-5-bromopent-3-en-1-ynyl]benzene
• CAS: 568571-18-6
• 化学式: C₁₁H₉Br
• 分子量: 221.096
• InChiKey: KFKLYSZHDZWMBN-KXFIGUGUSA-N

物化性质

• 沸点：
  285.5±32.0 °C(Predicted)
• 密度：
  1.36±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  12
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.09
• 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：

  2-溴-1H-吲哚-3-甲醛 、 (Z)-(5-bromopent-3-en-1-yn-1-yl)benzene 在 potassium carbonate 、 sodium iodide 作用下， 以 丙酮 为溶剂， 反应 48.0h， 以22%的产率得到2-bromo-1-[(Z)-5-phenylpent-2-en-4-ynyl]-1H-indole-3-carboxaldehyde
  参考文献：
  名称：

  Synthesis of Annulated γ-Carbolines and Heteropolycycles by the Palladium-Catalyzed Intramolecular Annulation of Alkynes

  摘要：

  A variety of N-substituted 2-bromo-1H-indole-3-carboxaldehydes incorporating an alkyne-containing tether on the indole nitrogen have been converted to the corresponding tert-butylimines, which have been subjected to palladium-catalyzed intramolecular iminoannulation, affording various gamma-carboline derivatives with an additional ring fused across the 4- and 5-positions in good to excellent yields. When the tethered carbon-carbon triple bond is terminal or substituted with a triethylsilyl group, the iminoannulation generates a tert-butyl-gamma-carbolinium salt as the major product. The palladium-catalyzed intramolecular annulations of N-substituted 2-bromo-1H-indole-3-carboxaldehyde, methyl 2-iodo-1H-indole-3-carboxylate, and 2-iodo-3-phenyl-1H-indole containing a phenylpentynyl tether produce the corresponding heteropolycycles in moderate to good yields.

  DOI：

  10.1021/jo0343228
• 作为产物：
  描述：

  (Z)-5-phenyl-2-penten-4-yn-1-ol 在 四溴化碳 、 三苯基膦 作用下， 以 二氯甲烷 为溶剂， 以95%的产率得到(Z)-(5-bromopent-3-en-1-yn-1-yl)benzene
  参考文献：
  名称：

  Synthesis of Annulated γ-Carbolines and Heteropolycycles by the Palladium-Catalyzed Intramolecular Annulation of Alkynes

  摘要：

  A variety of N-substituted 2-bromo-1H-indole-3-carboxaldehydes incorporating an alkyne-containing tether on the indole nitrogen have been converted to the corresponding tert-butylimines, which have been subjected to palladium-catalyzed intramolecular iminoannulation, affording various gamma-carboline derivatives with an additional ring fused across the 4- and 5-positions in good to excellent yields. When the tethered carbon-carbon triple bond is terminal or substituted with a triethylsilyl group, the iminoannulation generates a tert-butyl-gamma-carbolinium salt as the major product. The palladium-catalyzed intramolecular annulations of N-substituted 2-bromo-1H-indole-3-carboxaldehyde, methyl 2-iodo-1H-indole-3-carboxylate, and 2-iodo-3-phenyl-1H-indole containing a phenylpentynyl tether produce the corresponding heteropolycycles in moderate to good yields.

  DOI：

  10.1021/jo0343228

文献信息

• A stereoselective synthesis of (E)-1-halo-6,6-dimethyl-2-hepten-4-yne: a key intermediate for terbinafine
  作者：Shan-Yen Chou、Chin-Lu Tseng、Shyh-Fong Chen

  DOI：10.1016/s0040-4039(00)00511-6

  日期：2000.5

  A study of the stereoselective halogenation of 6,6-dimethyl-1-hepten-4-yn-3-ol (1) using a series of halogenating agents is described. Of the many agents investigated, boron trichloride is the most successful reagent for stereoselective halogenation (E:Z=9:1max). The resulting (E)-1-halo-6,6-dimethyl-2-hepten-4-yne (2), a key intermediate for terbinafine, an antifungal agent, is obtained in good yield

  描述了使用一系列卤化剂对6,6-二甲基-1-庚烯-4-yn-3-ol（1）进行立体选择性卤化的研究。在研究的许多试剂中，三氯化硼是最成功的立体选择性卤化试剂（E：Z = 9：1 max）。以良好的收率和立体选择性获得了所得的（E）-1-卤代-6,6-二甲基-2-庚基-4-炔（2），这是特比萘芬（一种抗真菌剂）的关键中间体。同样研究了两种结构相关的炔烃，并显示了相似的通用性。
• A highly practical approach to chiral homoallylic–homopropargylic amines via aza-Barbier reaction
  作者：Bin-Hua Yuan、Zhi-Cheng Zhang、Wen-Jie Liu、Xing-Wen Sun

  DOI：10.1016/j.tetlet.2016.03.103

  日期：2016.5

  The first access to chiral homoallylic–homopropargylic amine bearing two contiguous stereocenters has been well accomplished via zinc-promoted aza-Barbier reaction. N-tert-Butanesulfinyl ketimines are well-tolerated substrates, providing the tertiary amines in high yields and with excellent diastereoselectivities. 3,4-Dihydro-2H-pyrroles could be prepared in high efficiency by cyclization of the corresponding

  通过锌促进的氮杂-巴比尔反应已经很好地实现了首次获得具有两个连续立体中心的手性均烯丙基-同炔丙基胺。ñ -叔-Butanesulfinyl酮亚胺是耐受性良好的基板，提供以高收率和优异的非对映选择性的叔胺。通过将相应的胺环化，可以高效地制备3，4-二氢-2 H-吡咯。
• A New Co₂(CO)₈-Mediated Tandem [5 + 1]/[2 + 2 + 1]-Cycloaddition Reaction:  A One-Pot Synthesis of Tricyclic δ-Lactones from <i>cis</i>-Epoxy Ene-ynes
  作者：Arjan Odedra、Chang-Jung Wu、Reniguntala J. Madhushaw、Su-Lein Wang、Rai-Shung Liu

  DOI：10.1021/ja0346633

  日期：2003.8.1

  In the presence of Co2(CO)8 and CO, cis-epoxyalkynes bearing a tether olefin undergo a tandem [5 + 1]/[2 + 2 + 1]-cycloaddition to give tricyclic delta-lactones efficiently in a one-pot operation. The reaction mechanism is proposed to involve a cobalt-coordinated cyclic allene species.