bicyclo-<3.2.1>octan-3,8-dione | 70260-48-9

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: bicyclo-<3.2.1>octan-3,8-dione
• 英文别名: Bicyclo<3.2.1>octan-3,8-dion；(1S,5R)-bicyclo[3.2.1]octane-3,8-dione
• CAS: 70260-48-9
• 化学式: C₈H₁₀O₂
• 分子量: 138.166
• InChiKey: GLUULYCPFODBLV-OLQVQODUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.1
• 重原子数：
  10
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.75
• 拓扑面积：
  34.1
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  (1R,5S)-spiro[bicyclo[3.2.1]octane-8,2’-[1,3]dioxolan]-3-one 在 Amberlite IR 120 (H+) ionexchange resin 、 sodium isopropylate 作用下， 以 甲醇 、 水 为溶剂， 生成 bicyclo-<3.2.1>octan-3,8-dione
  参考文献：
  名称：

  立体和区域选择性加氧汞化-双环[3.2.1] Oct-2-ene骨架的脱汞

  摘要：

  报道了双环[[3.2.1] oct-2-en-8-one]的乙烯缩酮的氧化汞-脱汞。该反应以高区域选择性和立体选择性进行。

  DOI：

  10.1016/s0040-4039(01)80143-x

文献信息

• Bicyclo[3.3.1]nonanes as synthetic intermediates. IV. Behavior of bicyclo[3.n.1]alkan-3-ones toward the Baeyer-Villiger oxidation.
  作者：TAKEFUMI MOMOSE、OSAMU MURAOKA、SHOHGO ATARASHI、TAMIKO HORITA

  DOI：10.1248/cpb.27.222

  日期：——

  The Baeyer-Villiger oxidation of bicyclo [3. n. 1] alkan-3-ones and related systems is described. Bicyclo [3. 3. 1] nonan-2-one (8) was oxidized into the corresponding lactone, which was found to be converted into the cis-1, 3-disubstituted cyclohexane system by the subsequent methanolysis. Meanwhile, the 3-oxo system (2) manifested an anomalous inactivity against the oxidation. The"backside steric hindrance"caused by the axial (endo) proton at C-7 was postulated as the origin of the inactivity. The differential reactivity of the ketones in the Baeyer-Villiger reaction of the bicyclic systems (2, 3, 4) enabled the regiospecific lactonization of the bicyclic diketones (17, 18, 19) into the lactones (37, 38, 39), which would be important precursors for specifically substituted medium-sized lactones, to be achieved.

  描述了双环[3.n.1]烷-3-酮和相关系统的拜耳-维利格氧化。双环[3.3.1]壬烷-2-酮（8）被氧化成相应的内酯，发现通过后续的甲醇解转化为顺式-1,3-二取代环己烷系统。同时，3-氧代系统（2）表现出异常的抗氧化性。假设C-7处的轴向（内）质子引起的“背面空间位阻”是不活跃的根源。在双环系统（2、3、4）的拜耳-维利格反应中，酮
• Stereo- and regioselective oxymercuration - demercuration of bicyclo[3.2.1]Oct-2-ene skeleton
  作者：M. Povárny、P. Scheiber、G. Kraiss、K. Nádor

  DOI：10.1016/s0040-4039(01)80143-x

  日期：1984.1

  The oxymercuration - demercuration of ethylene ketal of bicyclo-[3.2.1]oct-2-en-8-one is reported. This reaction proceeds with high regio- and stereoselectivity.

  报道了双环[[3.2.1] oct-2-en-8-one]的乙烯缩酮的氧化汞-脱汞。该反应以高区域选择性和立体选择性进行。