3-(prop-2-yn-1-yloxy)cyclohex-1-ene | 104526-37-6

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 3-(prop-2-yn-1-yloxy)cyclohex-1-ene
• 英文别名: 2-cyclohexenyl propargyl ether；Cyclohexene, 3-(2-propynyloxy)-；3-prop-2-ynoxycyclohexene
• CAS: 104526-37-6
• 化学式: C₉H₁₂O
• 分子量: 136.194
• InChiKey: CWXGQPOAIWXAQI-UHFFFAOYSA-N

物化性质

• 沸点：
  205.8±28.0 °C(Predicted)
• 密度：
  0.94±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  10
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.56
• 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-(prop-2-yn-1-yloxy)cyclohex-1-ene 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-(1,2-Propadienyloxy)cyclohexene
  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)cyclohexane 在 1,8-二氮杂双环[5.4.0]十一碳-7-烯 作用下， 反应 5.0h， 以100%的产率得到3-(prop-2-yn-1-yloxy)cyclohex-1-ene
  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

• Et₃B Induced Radical Addition of Thiols to Acetylenes
  作者：Yoshifumi Ichinose、Kuni Wakamatsu、Kyoko Nozaki、Jean-Luc Birbaum、Koichiro Oshima、Kiitiro Utimoto

  DOI：10.1246/cl.1987.1647

  日期：1987.8.5

  Thiols added easily to acetylenic compounds in the presence of Et3B to give alkenyl sulfides in good yields. The reaction of acetylenes with 3-methyl-2-buten-1-thio1 gave dihydro-thiophene derivatives in one pot.

  在 Et3B 存在下，硫醇很容易添加到乙炔化合物中，从而以良好的收率得到烯基硫化物。乙炔与 3-methyl-2-buten-1-thio1 的反应在一锅中得到二氢噻吩衍生物。
• Regio- and stereo-specific addition of chlorodibutyltin hydride to prop-2-ynylic ethers
  作者：Terence N. Mitchell、Said-Nadjib Moschref

  DOI：10.1039/a802160k

  日期：——

  A number of prop-2-ynylic ethers smoothly undergo regio- and stereo-specific hydrostannation with chlorodibutyltin hydride in good to nearly quantitative yield at room temperature in benzene.

  多种丙-2-炔基醚在室温下与二丁基氯锡氢化物在苯中进行区域和立体特异性的氢锡化反应，反应顺利，产率良好，几乎接近定量。
• An efficient palladium-catalysed coupling of terminal alkynes with aryl halides under Jeffery's conditions
  作者：Jean-Flaubert Nguefack、Véronique Bolitt、Denis Sinou

  DOI：10.1016/0040-4039(96)01188-4

  日期：1996.7

  Palladium-catalysed coupling of terminal alkynes with aryl halides occurs at room temperature in quite good yields in the presence of a quaternary ammonium salt and a base in a acetonitrile-water solution, without any added cuprous iodide.

  在室温下，在乙腈水溶液中存在季铵盐和碱的情况下，钯催化的末端炔烃与芳基卤化物的偶合反应以非常好的收率进行，而无需添加任何碘化亚铜。
• Ether formation from allylic alcohols catalyzed by samarium trichloride
  作者：Mohsen Ouertani、Jacqueline Collin、Henri B. Kagan

  DOI：10.1016/s0040-4020(01)91389-4

  日期：1985.1

  behaviour of various allylic alcohols in the presence of catalytic amounts of SmCl3 (by heating in 1,2-dichloroethane) has been studied. Diallyl ethers are obtained in many cases in good yields. Mixed allyl alkyl ethers are also prepared if 2–5 equivalents of an aliphatic alcohol is present. The reactions are interpreted as proceeding through a pseudo allylic carbonium intermediate initiated by a preliminary

  已经研究了在催化量的SmCl 3存在下（通过在1,2-二氯乙烷中加热）各种烯丙醇的行为。在许多情况下以高收率获得二烯丙基醚。如果存在2-5当量的脂肪醇，也可以制备混合的烯丙基烷基醚。该反应被解释为通过烯丙基羟基与the离子的初步络合引发的拟烯丙基碳中间体进行。
• Reductive Addition of the Benzenethiyl Radical to Alkynes by Amine-Mediated Single Electron Transfer Reaction to Diphenyl Disulfide
  作者：Tsuyoshi Taniguchi、Tatsuya Fujii、Atsushi Idota、Hiroyuki Ishibashi

  DOI：10.1021/ol901084k

  日期：2009.8.6

  Hydrothiolation of alkynes proceeds with diphenyl disulfide and tripropylamine. Amine-mediated single electron transfer to diphenyl disulfide can be proposed for the reaction mechanism. Applications of the method to radical cyclizations of eneyne compounds are also presented.

  炔烃的氢硫基化与二苯基二硫化物和三丙胺一起进行。可以提出胺介导的单电子转移到二苯二硫的反应机理。还介绍了该方法在烯炔化合物自由基环化中的应用。