Trans-2-fluorocyclooct-5-en-1-ol | 108909-88-2

• 分子结构分类: 有机化合物 - 有机卤素化合物 - 卤代醇
• 英文名称: Trans-2-fluorocyclooct-5-en-1-ol
• 英文别名: 2-fluorocyclooct-5-en-1-ol；(1R,4Z,8R)-8-fluorocyclooct-4-en-1-ol
• CAS: 108909-88-2
• 化学式: C₈H₁₃FO
• 分子量: 144.189
• InChiKey: SOXGTJUXIWBHGQ-LQKKCHKWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  10
• 可旋转键数：
  0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.75
• 拓扑面积：
  20.2
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  Trans-2-fluorocyclooct-5-en-1-ol 在 (HF)10-pyridine 作用下， 生成 4-Fluoro-octahydro-pentalen-1-ol
  参考文献：
  名称：

  Reaction of hydrogen fluoride with cyclooctene compounds: aziridine and epoxide

  摘要：

  DOI：

  10.1016/s0022-1139(00)83376-x
• 作为产物：
  描述：

  (Z)-9-oxabicyclo[6.1.0]non-4-ene 在 氢氟酸 、 三乙胺 作用下， 反应 24.0h， 生成 Trans-2-fluorocyclooct-5-en-1-ol
  参考文献：
  名称：

  环辛烯化合物与氟化剂的反应

  摘要：

  对9-氧杂双环[6.1.0]非-4-烯与相应的氮丙啶的反应性的比较研究表明，环氧化物与几乎中性的氟化试剂（Et 3 N，3HF）发生开环反应，但未与任何氮丙啶。使用Olah试剂，在环氧化物的反应中观察到双键参与，而HF在相同条件下与9-氮杂双环[6.1.0] non-4-ene立体选择性地加成了HF，而没有氮丙啶环的参与。 。

  DOI：

  10.1016/s0022-1139(00)81933-8

文献信息

• Transannular oxygen participation in halofluorination reactions of 9-oxabicyclo[6.1.0]non-4-ene[1]
  作者：Günter Haufe、Gerard Alvernhe、Andre Laurent

  DOI：10.1016/s0022-1139(00)81561-4

  日期：1990.1

  The transannular O-heterocyclization of 9-oxabicyclo[6.1.0]non-4-ene in halofluorination reactions using N-halosuccinimides and triethylamine tris-hydrofluoride or Olah's reagent, respectively, yields endo, endo-2-halo-6-fluoro-9-oxabicyclo[3.3.1.]nonane as the main product and endo,endo-2-halo-5-fluoro-9-oxabicyclo[4.2.1.]nonane as the minor compound by halonium assisted epoxide ring participation

  分别使用N-卤代琥珀酰亚胺和三乙胺三氢氟化物或Olah试剂在卤代氟化反应中对9-氧杂双环[6.1.0] non-4-ene进行跨环O-杂环化，得到内，内-2-卤代-6-氟代-通过ha辅助的环氧基参与，以9-氧杂双环[3.3.1。]壬烷为主要产物和内消旋，内--2-卤代-5-氟-9-氧杂双环[4.2.1。]壬烷为次要化合物。
• Synthesis of fluoroalkyl methyl thioethers by formal addition of methanesulfenyl fluoride to alkenes
  作者：Gunter Haufe、Gerard Alvernhe、Daniel Anker、Andre Laurent、Christine Saluzzo

  DOI：10.1021/jo00028a056

  日期：1992.1

  The electrophilic anti-1,2-addition of the elements of methanesulfenyl fluoride to carbon-carbon double bonds by a one-pot reaction of dimethyl(methylthio)sulfonium tetrafluoroborate and triethylamine trishydrofluoride with various types of alkenes is used for the synthesis of beta-fluoroalkyl methyl thioethers. This reaction is stereospecific: starting from cis-cycloalkenes (1) trans-1-fluoro-2-(methylthio)cycloalkanes (2) are formed, while trans-cyclododecene (3) gives the cis product 4 everytime in good yields. With unsymmetrical alkenes these reactions proceed regioselectively to produce Markovnikov-oriented fluoro thioethers. With 2,6-norbornadiene (26) exclusive exo attack on one double bond and subsequent transannular participation of the second pi-bond gives rise to two isomeric 3,5-disubstituted nortricyclanes, 28 and 29, while starting from the medium-sized cis,cis-1,5-cyclooctadiene (10) no transannular pi-participation is observed: the trans-1,2-addition product to one of the two double bonds in 11 is isolated. In contrast, in the reaction of the monoepoxide 30 of this diene in addition to the simple 1,2-adduct 31 a transannular oxygen participation occurs producing three oxa bicyclic compounds 32-34. The oxidation of 1-fluoro-2-(methylthio)cyclooctane (2a) by sodium periodate yields the expected mixture of two diastereomeric 1-fluoro-2-(methylsulfinyl)cyclooctanes (36) which on pyrolysis give 3-fluorocyclooctene (37).
• Kalow, Julia A.; Doyle, Abigail G., Journal of the American Chemical Society, 2010, vol. 132, p. 3268 - 3269
  作者：Kalow, Julia A.、Doyle, Abigail G.

  DOI：——

  日期：——
• ALVERNHE G.; LAURENT A.; HAUFE G., J. FLUOR. CHEM., 34,(1986) N 1, 147-156
  作者：ALVERNHE G.、 LAURENT A.、 HAUFE G.

  DOI：——

  日期：——
• Triethylamine Trishydrofluoride in Synthesis
  作者：G�nter Haufe

  DOI：10.1002/prac.19963380122

  日期：——