7-phenyl-2-oxabicyclo[3.3.0]oct-6-ene | 216985-79-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 7-phenyl-2-oxabicyclo[3.3.0]oct-6-ene
• 英文别名: 5-phenyl-3,5,6,6a-tetrahydro-2H-cyclopenta[b]furan
• CAS: 216985-79-4
• 化学式: C₁₃H₁₄O
• 分子量: 186.254
• InChiKey: RBIZFJIBIPEBQH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  14
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  9.2
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  7-phenyl-2-oxabicyclo[3.3.0]oct-6-ene 在 thexylborane-dimethylsulfide 、 sodium hydroxide 、 双氧水 作用下， 以 四氢呋喃 、 乙醇 为溶剂， 反应 27.0h， 以41%的产率得到(1R*,2S*,3S*,5S*)-3-phenyl-6-oxabicyclo[3.3.0]octan-2-ol
  参考文献：
  名称：

  Tandem Cyclization of Alkynylmetals Bearing a Remote Leaving Group via Cycloalkylidene Carbenes

  摘要：

  Treatment of terminal alkynes bearing a remote leaving group with MNR2 (M = Li, Na, K) gives bicyclo[n.3.0]-1-alkenes (n = 3, 4). The tandem cyclization proceeds through a mechanism involving exo-cyclization of an alkynylmetal intermediate and intramolecular C-H insertion of the resulting carbenoid.

  DOI：

  10.1021/ol0059145
• 作为产物：
  描述：

  4-Fluoro-benzenesulfonic acid 2-(1-phenethyl-prop-2-ynyloxy)-ethyl ester 在 正丁基锂 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 以55%的产率得到7-phenyl-2-oxabicyclo[3.3.0]oct-6-ene
  参考文献：
  名称：

  Generation of Cycloalkylidene Carbenes via Exo-Type Cyclization of Alkynyllithiums Bearing Remote Leaving Group

  摘要：

  The reaction of 5-hexynyl tosylate (3a) with alkynyllithium (RC=CLi; R Ph, TMS) gives enynes 5 and 6. The reaction proceeds through a mechanism involving a novel exo-type cyclization of 6-lithiod-hexynyl tosylate to form cyclopentylidene carbene. Enyne 6 is produced by the addition of RC=CLi to the carbene, whereas rearrangement of the carbene to cyclohexyne followed by carbolithiation with RC=CLi gives enyne 5. The formation of cyclopentylidene carbene and cyclohexyne as intermediates is clearly demonstrated by trapping experiments with cyclohexene land triethylsilane) and with 1,3-diphenylisobenzofuran, respectively. Alkynyllithiums derived from 3-butynyl and 6-heptynyl p-fluorobenzenesulfonates (19a,b) undergo a similar exo-type cyclization to give cyclopropylidene and cyclohexylidene carbenes, respectively.

  DOI：

  10.1021/jo981411p

文献信息

• Generation of Cycloalkylidene Carbenes via Exo-Type Cyclization of Alkynyllithiums Bearing Remote Leaving Group
  作者：Toshiro Harada、Katsuhiro Iwazaki、Takeshi Otani、Akira Oku

  DOI：10.1021/jo981411p

  日期：1998.11.1

  The reaction of 5-hexynyl tosylate (3a) with alkynyllithium (RC=CLi; R Ph, TMS) gives enynes 5 and 6. The reaction proceeds through a mechanism involving a novel exo-type cyclization of 6-lithiod-hexynyl tosylate to form cyclopentylidene carbene. Enyne 6 is produced by the addition of RC=CLi to the carbene, whereas rearrangement of the carbene to cyclohexyne followed by carbolithiation with RC=CLi gives enyne 5. The formation of cyclopentylidene carbene and cyclohexyne as intermediates is clearly demonstrated by trapping experiments with cyclohexene land triethylsilane) and with 1,3-diphenylisobenzofuran, respectively. Alkynyllithiums derived from 3-butynyl and 6-heptynyl p-fluorobenzenesulfonates (19a,b) undergo a similar exo-type cyclization to give cyclopropylidene and cyclohexylidene carbenes, respectively.
• Tandem Cyclization of Alkynylmetals Bearing a Remote Leaving Group via Cycloalkylidene Carbenes
  作者：Toshiro Harada、Takayuki Fujiwara、Katsuhiro Iwazaki、Akira Oku

  DOI：10.1021/ol0059145

  日期：2000.6.1

  Treatment of terminal alkynes bearing a remote leaving group with MNR2 (M = Li, Na, K) gives bicyclo[n.3.0]-1-alkenes (n = 3, 4). The tandem cyclization proceeds through a mechanism involving exo-cyclization of an alkynylmetal intermediate and intramolecular C-H insertion of the resulting carbenoid.