3-(2-propynyloxy)cyclopentene | 150546-27-3

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 3-(2-propynyloxy)cyclopentene
• 英文别名: 3-(2-Propyn-1-yloxy)cyclopentene；3-Prop-2-ynoxycyclopentene
• CAS: 150546-27-3
• 化学式: C₈H₁₀O
• 分子量: 122.167
• InChiKey: FRELWVIYUNGQAN-UHFFFAOYSA-N

物化性质

• 沸点：
  182.8±28.0 °C(predicted)
• 密度：
  0.95±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.3
• 重原子数：
  9
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.5
• 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：

  3-(2-propynyloxy)cyclopentene 在 18-冠醚-6 potassium tert-butylate 作用下， 以 正戊烷 、 苯 为溶剂， 反应 16.0h， 生成 2-(Cyclopenten-3-yl)propenal
  参考文献：
  名称：

  Allenyl allylic ethers: synthesis and thermal rearrangements

  摘要：

  Application of the sequence halogenation/dehydrohalogenation/isomerization to alkenes 1a-g affords allenyl allylic ethers 5a-g. Thermal isomerizations of 5a,d,e proceed by Claisen rearrangement, while 5b,c,f,g are transformed by alternate modes of [2 + 2]cycloaddition involving biradical intermediates of type 19 to polycyclic structures; the variations in these thermal isomerizations are mainly a function of ring size.

  DOI：

  10.1021/jo00073a032
• 作为产物：
  描述：

  trans-1-Bromo-2-(2-propyn-1-yloxy)cyclopentane 在 1,8-二氮杂双环[5.4.0]十一碳-7-烯 作用下， 反应 5.0h， 以80%的产率得到3-(2-propynyloxy)cyclopentene
  参考文献：
  名称：

  Allenyl allylic ethers: synthesis and thermal rearrangements

  摘要：

  Application of the sequence halogenation/dehydrohalogenation/isomerization to alkenes 1a-g affords allenyl allylic ethers 5a-g. Thermal isomerizations of 5a,d,e proceed by Claisen rearrangement, while 5b,c,f,g are transformed by alternate modes of [2 + 2]cycloaddition involving biradical intermediates of type 19 to polycyclic structures; the variations in these thermal isomerizations are mainly a function of ring size.

  DOI：

  10.1021/jo00073a032

文献信息

• Regio- and stereo-controlled synthesis of bicyclic α-methylene-γ-butyrolactones containing a fluorine via halofluorination-radical cyclization
  作者：Makoto Shimizu、Osamu Morita、Satoru Itoh、Tamotsu Fujisawa

  DOI：10.1016/s0040-4039(00)60917-6

  日期：1992.11

  regio- and stereoselective halofluorination with pyridinium poly(hydrogen fluoride) and 1,3-dibromo-5,5-dimethylhydantoion or N-iodosuccinimide to give (1S*,2S*,3S*)-1-alkoxy-3-fluoro-2-halocycloalkanes in good yields. Among the halofluorides, the 3-(2-propynyloxy) derivatives are in turn converted into bicyclic α-methylene-γ-butyrolactons containing a fluorine via radical cyclization followed by oxidation

  3-烷氧基环烯烃与吡啶鎓聚（氟化氢）和1,3-二溴-5,5-二甲基乙内酰脲或N-碘代琥珀酰亚胺进行区域和立体选择性卤代氟化反应，得到（1 S *，2 S *，3 S *）-1-烷氧基-3-氟-2-卤代环烷烃收率高。在卤代氟化物中，3-（2-丙炔氧基）衍生物通过自由基环化反应继而被氧化成含氟的双环α-亚甲基-γ-丁内酯，然后氧化，导致立体立体合成（±）-4-氟- l- Epi- damsin。
• Domino metathesis of alkynyl substituted cycloolefins
  作者：Anke Rückert、Dirk Eisele、Siegfried Blechert

  DOI：10.1016/s0040-4039(01)01003-6

  日期：2001.7

  Cycloolefins with N- and O-propargyl side chains were converted in good yields to disubstituted dihydropyrroles and dihydrofurans using Grubbs' catalyst in a sequence of enyne metathesis, RCM-ROM and CM. Olefins employed in the final CM step were ethylene and various monosubstituted alkenes. (C) 2001 Elsevier Science Ltd. All rights reserved.