(E)-7-bromo-5-methylhept-5-en-1-yne | 1163722-62-0

• 分子结构分类: 有机化合物 - 乙炔化物
• 英文名称: (E)-7-bromo-5-methylhept-5-en-1-yne
• CAS: 1163722-62-0
• 化学式: C₈H₁₁Br
• 分子量: 187.079
• InChiKey: FFLDNLGSQQJSPY-SOFGYWHQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  9
• 可旋转键数：
  3
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.5
• 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：

  (E)-7-bromo-5-methylhept-5-en-1-yne 在 [(CyJohnPhos)Au(MeCN)]SbF₆ 、 sodium hydride 作用下， 以 四氢呋喃 、 二氯甲烷 、 mineral oil 为溶剂， 反应 25.5h， 生成 C₂₁H₂₂O₅
  参考文献：
  名称：

  宽范围金（i）催化的多烯炔环化反应，最多可形成四个碳-碳键†

  摘要：

  金（I）催化的多烯炔的多环化已首次扩展为同时形成多达四个碳-碳键，从而在一步法制备的类固醇类分子中具有高立体选择性，且催化剂负载量低。除末端炔烃外，溴炔烃还可用作多烯环化反应的引发剂，从而产生了合成上有用的环状溴烯烃。

  DOI：

  10.1039/c7ob00235a
• 作为产物：
  描述：

  (E)-6-acetoxy-4-methyl-4-hexenal 在 甲醇 、 三溴化磷 、 potassium carbonate 作用下， 以 乙醚 、 水 为溶剂， 反应 8.0h， 生成 (E)-7-bromo-5-methylhept-5-en-1-yne
  参考文献：
  名称：

  Useful Catalytic Enantioselective Cationic Double Annulation Reactions Initiated at an Internal π-Bond: Method and Applications

  摘要：

  The 1:1 complex of o,o'-dichloro-R-BINOL and SbCl5 initiates the enantioselective cationic polycyclization of polyunsaturated substrates at a predictable pi-bond which may be either terminal or, as shown herein, internal. The extension of this powerful construction to internal pi-bonds expands the scope of this method and opens up very short pathways to numerous chiral polycyclic molecules, including natural products and their analogues. Especially simple synthetic routes are disclosed that provide access to dysideapalaunic acid, dehydroabietic acid, and epipodocarpic acid and illustrate, the value of this enantioselective approach.

  DOI：

  10.1021/ja4125093

文献信息

• Useful Catalytic Enantioselective Cationic Double Annulation Reactions Initiated at an Internal π-Bond: Method and Applications
  作者：Karavadhi Surendra、Goreti Rajendar、E. J. Corey

  DOI：10.1021/ja4125093

  日期：2014.1.15

  The 1:1 complex of o,o'-dichloro-R-BINOL and SbCl5 initiates the enantioselective cationic polycyclization of polyunsaturated substrates at a predictable pi-bond which may be either terminal or, as shown herein, internal. The extension of this powerful construction to internal pi-bonds expands the scope of this method and opens up very short pathways to numerous chiral polycyclic molecules, including natural products and their analogues. Especially simple synthetic routes are disclosed that provide access to dysideapalaunic acid, dehydroabietic acid, and epipodocarpic acid and illustrate, the value of this enantioselective approach.
• Broad scope gold(<scp>i</scp>)-catalysed polyenyne cyclisations for the formation of up to four carbon–carbon bonds
  作者：Zhouting Rong、Antonio M. Echavarren

  DOI：10.1039/c7ob00235a

  日期：——

  The polycyclisation of polyenynes catalyzed by gold(I) has been extended for the first time to the simultaneous formation of up to four carbon–carbon bonds, leading to steroid-like molecules with high stereoselectivity in a single step with low catalyst loadings. In addition to terminal alkynes, bromoalkynes can also be used as initiators of polyene cyclisations, giving rise to synthetically useful

  金（I）催化的多烯炔的多环化已首次扩展为同时形成多达四个碳-碳键，从而在一步法制备的类固醇类分子中具有高立体选择性，且催化剂负载量低。除末端炔烃外，溴炔烃还可用作多烯环化反应的引发剂，从而产生了合成上有用的环状溴烯烃。