11-oxotricyclo<4.4.2.0^1,6>dodeca-3,8-dienyl 12-methanesulfonate | 142566-63-0

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 有机磺酸及其衍生物
• 英文名称: 11-oxotricyclo<4.4.2.0^1,6>dodeca-3,8-dienyl 12-methanesulfonate
• 英文别名: (12-Oxo-11-tricyclo[4.4.2.01,6]dodeca-3,8-dienyl) methanesulfonate
• CAS: 142566-63-0
• 化学式: C₁₃H₁₆O₄S
• 分子量: 268.334
• InChiKey: VOUYJOKLHLNOBK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  18
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.62
• 拓扑面积：
  68.8
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  11-oxotricyclo<4.4.2.0^1,6>dodeca-3,8-dienyl 12-methanesulfonate 在 lithium hydroxide 作用下， 以 四氢呋喃 为溶剂， 反应 24.0h， 以96%的产率得到<4.4.1>propella-3,8-diene-11-carboxylic acid
  参考文献：
  名称：

  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

  摘要：

  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.

  DOI：

  10.1021/ja00102a020
• 作为产物：
  描述：

  12-hydroxy-11-oxotricyclo<4.4.2.0^1,6>dodeca-3,8-diene 以96%的产率得到
  参考文献：
  名称：

  Barrett David G., Liang Gui-Bal, McQuade D. Tyler, Desper John M., Schlad+, J. Amer. Chem. Soc, 116 (1994) N 23, S 10525-10532

  摘要：

  DOI：

文献信息

• Barrett David G., Liang Gui-Bal, McQuade D. Tyler, Desper John M., Schlad+, J. Amer. Chem. Soc, 116 (1994) N 23, S 10525-10532
  作者：Barrett David G., Liang Gui-Bal, McQuade D. Tyler, Desper John M., Schlad+

  DOI：——

  日期：——
• 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.