3-(2-丙炔-1-基氧基)环庚烯 | 150546-31-9

• 分子结构分类: 有机化合物 - 有机氧化合物
• 中文名称: 3-(2-丙炔-1-基氧基)环庚烯
• 英文名称: 3-(2-propynyloxy)cycloheptene
• 英文别名: 3-(2-Propyn-1-yloxy)cycloheptene；3-Prop-2-ynoxycycloheptene
• CAS: 150546-31-9
• 化学式: C₁₀H₁₄O
• 分子量: 150.221
• InChiKey: JOSFXENEDGPHNR-UHFFFAOYSA-N

物化性质

• 沸点：
  227.9±28.0 °C(Predicted)
• 密度：
  0.93±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  11
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.6
• 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-丙炔-1-基氧基)环庚烯 在 18-冠醚-6 potassium tert-butylate 作用下， 以 正戊烷 为溶剂， 反应 12.0h， 以100%的产率得到3-(丙二烯基氧基)环庚烯
  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)cycloheptane 在 1,8-二氮杂双环[5.4.0]十一碳-7-烯 作用下， 反应 5.0h， 以98%的产率得到3-(2-丙炔-1-基氧基)环庚烯
  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。
• Allenyl allylic ethers: synthesis and thermal rearrangements
  作者：Jean Pierre Dulcere、Jack Crandall、Robert Faure、Maurice Santelli、Valerie Agati、Mohamed N. Mihoubi

  DOI：10.1021/jo00073a032

  日期：1993.10

  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.