8-oxo-4-oxatetracyclo<4.2.1.0^2,5.0^3,7>nonane | 82431-33-2

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 异戊烯醇脂质
• 英文名称: 8-oxo-4-oxatetracyclo<4.2.1.0^2,5.0^3,7>nonane
• 英文别名: 4-oxatetracyclo[4.2.1.0.^2,50^3,7]nonan-8-one；4-oxatetracyclo[4.2.1.02,5.03,7]nonan-8-one
• CAS: 82431-33-2
• 化学式: C₈H₈O₂
• 分子量: 136.15
• InChiKey: QNTUZWBPVHJFPY-UHFFFAOYSA-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：
  5.0
• sp3杂化的碳原子比例：
  0.88
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  8-oxo-4-oxatetracyclo<4.2.1.0^2,5.0^3,7>nonane 在 草酰氯 、 lithium 、 三乙基硼氢化锂 、 二甲基亚砜 、 三乙胺 作用下， 以 四氢呋喃 、 二氯甲烷 、 乙二胺 为溶剂， 反应 17.0h， 生成 2,6-stelladione
  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：

  endo-2-formyl-3-methylenebicyclo<2.2.1>hept-5-ene 在 水 、 氧气 、 臭氧 、 溶剂黄146 、 锌 作用下， 以 苯 为溶剂， 反应 20.0h， 生成 8-oxo-4-oxatetracyclo<4.2.1.0^2,5.0^3,7>nonane
  参考文献：
  名称：

  Synthesis of the D2d-dinoradamantane derivatives having two coaxially oriented unsaturated centers. 6-Methylene-D2d-dinoradamantan-2-one and D2d-dinoradamantane-2,6-dione

  摘要：

  DOI：

  10.1021/jo00139a017

文献信息

• Gleiter, Rolf; Borzyk, Oliver, Angewandte Chemie, 1995, vol. 107, # 9, p. 1094 - 1095
  作者：Gleiter, Rolf、Borzyk, Oliver

  DOI：——

  日期：——
• NAKAZAKI, MASAO;NAEMURA, KOICHIRO;HARADA, HIROSHI;NARUTAKI, HIDEYA, J. ORG. CHEM., 1982, 47, N 18, 3470-3474
  作者：NAKAZAKI, MASAO、NAEMURA, KOICHIRO、HARADA, HIROSHI、NARUTAKI, HIDEYA

  DOI：——

  日期：——
• Synthesis of the D2d-dinoradamantane derivatives having two coaxially oriented unsaturated centers. 6-Methylene-D2d-dinoradamantan-2-one and D2d-dinoradamantane-2,6-dione
  作者：Masao Nakazaki、Koichiro Naemura、Hiroshi Harada、Hideya Narutaki

  DOI：10.1021/jo00139a017

  日期：1982.8
• Syntheses and Structural Properties of Distellenes
  作者：Rolf Gleiter、Gerd Fritzsche、Oliver Borzyk、Thomas Oeser、Frank Rominger、Hermann Irngartinger

  DOI：10.1021/jo971938m

  日期：1998.5.1

  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.