syn-11-carbomethoxy-3-phenyl-1,6-methano<10>annulene | 142566-75-4

• 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: syn-11-carbomethoxy-3-phenyl-1,6-methano<10>annulene
• 英文别名: anti-11-carbomethoxy-3-phenyl-1,6-methano<10>annulene；methyl 3-phenylbicyclo[4.4.1]undeca-1(10),2,4,6,8-pentaene-11-carboxylate
• CAS: 142566-75-4
• 化学式: C₁₉H₁₆O₂
• 分子量: 276.335
• InChiKey: GIXDMSQWYCPVNA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.4
• 重原子数：
  21
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.11
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  methyl 4-phenyl<4.4.1>propella-2,8-diene-11-carboxylate 在 2,3-二氯-5,6-二氰基-1,4-苯醌 作用下， 以 1,4-二氧六环 为溶剂， 生成 syn-11-carbomethoxy-3-phenyl-1,6-methano<10>annulene
  参考文献：
  名称：

  New synthesis of methano-bridged annulenes: access to highly substituted derivatives

  摘要：

  DOI：

  10.1021/ja00043a046

文献信息

• New synthesis of methano-bridged annulenes: access to highly substituted derivatives
  作者：David G. Barrett、Gui Bai Liang、Samuel H. Gellman

  DOI：10.1021/ja00043a046

  日期：1992.8
• Synthetic Studies on the 1,6-Methano[10]annulene Skeleton: A New Route That Provides Derivatives Substituted at the Bridge and on the Annulene Ring
  作者：David G. Barrett、Gui-Bai Liang、D. Tyler McQuade、John M. Desper、Kurt D. Schladetzky、Samuel H. Gellman

  DOI：10.1021/ja00102a020

  日期：1994.11

  A new synthetic route to the 1,6-methano[10]annulene skeleton has been developed. The key step in this route is the semi-benzylic Favorskii rearrangement of a [4.4.2]propellane to a [4.4.1]propellane. The methodology discussed here provides access to 1,6-methano[10]annulene derivatives bearing substituents on both the bridge carbon and the annulene ring. Control of the relative positioning of these appendages is achieved by introducing the annulene substituent via cuprate addition to an allylic lactone.