tricyclo[3.3.0.0^3,7]octane-2,4-diol | 208830-70-0

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: tricyclo[3.3.0.0^3,7]octane-2,4-diol
• CAS: 208830-70-0
• 化学式: C₈H₁₂O₂
• 分子量: 140.182
• InChiKey: FOVLXMJESFHTTA-CBUHOJLWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.01
• 重原子数：
  10.0
• 可旋转键数：
  0.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  40.46
• 氢给体数：
  2.0
• 氢受体数：
  2.0

反应信息

• 作为反应物：
  描述：

  tricyclo[3.3.0.0^3,7]octane-2,4-diol 在 2,6-二甲基吡啶 、 草酰氯 、 二甲基亚砜 、 三乙胺 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 30.25h， 生成 2-(triisopropylsiloxy)tricyclo[3.3.0.0^3,7]octan-4-one
  参考文献：
  名称：

  Syntheses and Structural Properties of Distellenes

  摘要：

  The syntheses of a mixture of the racemic (a) and the meso form (b) of several derivatives of 2,2'-bi(tricyclo[3.3.0.0(3,7)]octylidene) are described: The 6,6'-diisopropylidene- (4), 6,6'-dimethylidene- (5), 6,6'-dione- (6), syn-4,4'-dione- (7), anti-4,4'-dione- (8), syn-4-methylidene-4'-one- (9), anti-4-methylidene-4'-one- (10), syn-4,4'-dimethylidene- (11), and anti-4,4'-dimethylidene- (12) derivatives. Starting materials for all compounds were tricyclo[3.3.0.0(3,7)]octane-2,4-diol (19) and its 2,6-isomer 20. Key reaction was the McMurry coupling of 6-isopropylidenetricyclo[3.3.0.0(3,7)]octa (23) or 6-methylidenetricyclo[3.3.0.0(3,7)]octan-2-one (24) to yield 4 or 5, respectively. The McMurry coupling of the ketone 26 yielded 7 and 8. From the latter, species 9-12 could be generated via the Wittig reaction. In most cases only the racemates could be isolated. X-ray investigations on 4a revealed a separation of the isopropylidene groups by 10.3 Angstrom. The central C-C bridging bonds of the stellane units in 4a, 7a, 8a, 12a, and 30 C(1)-C(5), C(3)-C(7), C(1)-C(5'), C(3')-C(7') were found to be between 1.596(2) and 1.616(3) Angstrom. In 4a we found a twisting between the terminal isopropylidene groups by a torsion ((CH3)(2)C=C ... C=C(CH3)(2)) of 74 degrees and 83 degrees, respectively, in both independent molecules. The twist angle between the CO groups in 7a amounts to 53 degrees, and in 8a to 118 degrees. The same twist angle was found between the exo-methylidene groups in 12a.

  DOI：

  10.1021/jo971938m
• 作为产物：
  描述：

  8-isopropylidene-4-oxatetracyclo[4.2.1.0.^2,50^3,7]nonane 在 2,3-二巯基丁二酸 、 lithium 、 三乙基硼氢化锂 、 臭氧 作用下， 以 四氢呋喃 、 二氯甲烷 、 乙二胺 为溶剂， 反应 17.0h， 生成 tricyclo[3.3.0.0^3,7]octane-2,4-diol
  参考文献：
  名称：

  Syntheses and Structural Properties of Distellenes

  摘要：

  The syntheses of a mixture of the racemic (a) and the meso form (b) of several derivatives of 2,2'-bi(tricyclo[3.3.0.0(3,7)]octylidene) are described: The 6,6'-diisopropylidene- (4), 6,6'-dimethylidene- (5), 6,6'-dione- (6), syn-4,4'-dione- (7), anti-4,4'-dione- (8), syn-4-methylidene-4'-one- (9), anti-4-methylidene-4'-one- (10), syn-4,4'-dimethylidene- (11), and anti-4,4'-dimethylidene- (12) derivatives. Starting materials for all compounds were tricyclo[3.3.0.0(3,7)]octane-2,4-diol (19) and its 2,6-isomer 20. Key reaction was the McMurry coupling of 6-isopropylidenetricyclo[3.3.0.0(3,7)]octa (23) or 6-methylidenetricyclo[3.3.0.0(3,7)]octan-2-one (24) to yield 4 or 5, respectively. The McMurry coupling of the ketone 26 yielded 7 and 8. From the latter, species 9-12 could be generated via the Wittig reaction. In most cases only the racemates could be isolated. X-ray investigations on 4a revealed a separation of the isopropylidene groups by 10.3 Angstrom. The central C-C bridging bonds of the stellane units in 4a, 7a, 8a, 12a, and 30 C(1)-C(5), C(3)-C(7), C(1)-C(5'), C(3')-C(7') were found to be between 1.596(2) and 1.616(3) Angstrom. In 4a we found a twisting between the terminal isopropylidene groups by a torsion ((CH3)(2)C=C ... C=C(CH3)(2)) of 74 degrees and 83 degrees, respectively, in both independent molecules. The twist angle between the CO groups in 7a amounts to 53 degrees, and in 8a to 118 degrees. The same twist angle was found between the exo-methylidene groups in 12a.

  DOI：

  10.1021/jo971938m