全氟双环(3.2.0)庚烷 | 85625-40-7

• 分子结构分类: 有机化合物 - 有机卤素化合物 - 有机氟化物
• 中文名称: 全氟双环(3.2.0)庚烷
• 英文名称: dodecafluorobicyclo(3,2,0)heptane
• 英文别名: 1,2,2,3,3,4,4,5,6,6,7,7-dodecafluorobicyclo[3.2.0]heptane
• CAS: 85625-40-7
• 化学式: C₇F₁₂
• 分子量: 312.058
• InChiKey: JDUQERPOVDKZAB-UHFFFAOYSA-N

物化性质

• 熔点：
  22 °C
• 沸点：
  73.2±35.0 °C(Predicted)
• 密度：
  1.81±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.61
• 重原子数：
  19.0
• 可旋转键数：
  0.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  0.0
• 氢给体数：
  0.0
• 氢受体数：
  0.0

反应信息

• 作为反应物：
  描述：

  全氟双环(3.2.0)庚烷 反应 22.0h， 以85%的产率得到全氟环戊烯
  参考文献：
  名称：

  Thermal and Photochemistry of Perfluoro-1,6-heptadiene and the Perfluoro-1,3,6-heptatrienes

  摘要：

  Pyrolysis transformed the title diene (1) into a 9:1 mixture of perfluorobicyclo[3.1.1]heptane (2) and cis-perfluorobicyclo[3.2.0]heptane (3) at 300 degrees C and at > 450 degrees C principally into perfluarocyclopentene (11). Mercury-sensitized vapor phase photolysis of 1 also yielded 2 and 3, but the latter now dominated and its trans isomer 13 was formed as well. In the presence of nitrogen as a bath gas, the product was further enriched in the [3.2.0] isomers. Radical bromination of 1, a model reaction for the triplet photocyclization, gave cis- and trans-perfluoro-1,2-bis(bromomethyl)cyclopentane (IB). Configurations were assigned to the cis and trans isomers of perfluoro-1,3,6-heptatriene (19 and 20), and they were equilibrated with iodine/visible light (K-t-->c = 1.6(7) in CDCl3, 14 degrees C). The cis triene underwent electrocyclization at 133 degrees C to perfluoro-3-allylcyclobutene (27); thermal ring opening of this cyclobutene yielded exclusively the cis isomer. At 250 degrees C both the cis triene and the allylcyclobutene were transformed quantitatively into perfluorobicyclo[3.1.1]hept-2-ene (28). Trans triene gave no detectable cyclobutene over a range of temperatures, but yielded the [3.1.1] compound at 250 degrees C. Ultraviolet irradiation of cis triene produced the allylcyclobutene, and mercury photosensitization of either compound (or the trans triene) proceeded a step farther to give tricycloheptane valence isomers (31 and 32). The internal [2 + 2] cycloadditions described here contribute to our knowledge of the ground rules for reactions of this type in unsaturated fluorocarbons.

  DOI：

  10.1021/jo00106a019
• 作为产物：
  描述：

  Perfluoro-1,6-heptadiene 生成 全氟双环(3.2.0)庚烷
  参考文献：
  名称：

  Jing Naiyong, Lemal David M., J. Org. Chem, 60 (1995) N 1, S 89-96

  摘要：

  DOI：

文献信息

• Polyfluoro-compounds based on the cycloheptane ring system. Part 6. Bicyclic compounds derived from nonafluorocyclohepta-1, 3-dienes and from octafluorocyclohepta-1, 3, 5-triene
  作者：David J. Dodsworth、Charles M. Jenkins、Robert Stephens、John Colin Tatlow

  DOI：10.1016/s0022-1139(00)83171-1

  日期：1984.4

  5-dimethoxy-compound. A Diels-Alder reaction between ethylene and 1H-nonafluorocyclohepta-1, 3- diene afforded 1H,8H,8H,9H,9H-nonafluoro-bicyclo(3,2,2)non-6-ene. Cobalt (III) fluoride at 300°C converted this principally to 1H-pentadecafluoro- bicyclo(3,2,2)nonane. The bridgehead hydrogen of this was exchanged for deuterium using deuterium oxide alone or containing potassium hydroxide. However, dehydrofluorination

  1H-，2H-和5H-九氟-和1H，4H-八氟-环庚1,3二烯通过形成交叉环键提供了相应的H-取代的多氟双环（3，2，0）-庚6-烯。在位置1和位置4之间。八氟环庚-1、3、5-三烯类似地得到八氟双环-（3,2,0）七-2,6-二烯。通过在100°C下通过氟化钴（III），1H-双环-6-烯生成1H-十一碳双环（3，2，0）庚烷，然后生成相应的碳氟化合物。1H-双环烷的桥头氢足够酸性，可以单独或含有一些氢氧化钾的氘与氧化氘交换氘，但长时间暴露于钾水溶液中则得到十氟双环（3，2，0）庚-1（5）-烯。丙酮中的高锰酸钾将其氧化，得到十氟-1，5-二羟基-8-氧杂双环（3，2，1）辛烷（水合），将其通过重氮甲烷甲基化为相应的1，5-二甲氧基化合物。乙烯与1H-九氟环庚-1-1，3-二烯之间的Diels-Alder反应得到1H，8H，8H，9H，9H-九氟双环（3,2,2）非6-烯。氟化钴（III
• Polyfluoro-compounds based on the cycloheptane ring system. Part 3. Bicyclic compounds made from decafluorocyclohepta-1,3-diene
  作者：Abd E.M.M. Khalil、Robert Stephens、John Colin Tatlow

  DOI：10.1016/s0022-1139(00)81488-8

  日期：1983.1
• KHALIL, ABD, E. M. M.;STEPHENS, R.;COLIN, TATLOW, J., J. FLUOR. CHEM., 1983, 22, N 1, 43-50
  作者：KHALIL, ABD, E. M. M.、STEPHENS, R.、COLIN, TATLOW, J.

  DOI：——

  日期：——
• DODSWORTH, D. J.;JENKINS, CH. M.;STEPHENS, R.;TATLOW, J. C., J. FLUOR. CHEM., 1984, 24, N 4, 509-522
  作者：DODSWORTH, D. J.、JENKINS, CH. M.、STEPHENS, R.、TATLOW, J. C.

  DOI：——

  日期：——