1-(3-isopropenylprop-2-yn-1-yl)piperidine | 19837-32-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 哌啶类
• 英文名称: 1-(3-isopropenylprop-2-yn-1-yl)piperidine
• 英文别名: 1-(4-Methylpent-4-en-2-yn-1-yl)piperidine；1-(4-methylpent-4-en-2-ynyl)piperidine
• CAS: 19837-32-2
• 化学式: C₁₁H₁₇N
• mdl: MFCD06619354
• 分子量: 163.263
• InChiKey: RBVXJKOFMBSDJR-UHFFFAOYSA-N

物化性质

• 沸点：
  82-83 °C(Press: 2-3 Torr)
• 密度：
  0.910±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  12
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.636
• 拓扑面积：
  3.2
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  1-(3-isopropenylprop-2-yn-1-yl)piperidine 在 甲醇 、 氢氧化钾 作用下， 以 乙醚 、 乙腈 为溶剂， 生成 1-(1-allyl-3-isopropenylprop-2-yn-1-yl)piperidine
  参考文献：
  名称：

  Synthesis of dialkyl(1-allyl-3-arylprop-2-yn-1-yl)-and dialkyl(1-allyl-3-alkenylprop-2-yn-1-yl)amines by the stevens rearrangement

  摘要：

  The Stevens rearrangement of dialkyl(allyl)(3-arylprop-2-yn-1-yl)- and dialkyl(allyl)(3-alkenylprop-2-yn-1-yl)ammonium bromides gave dialkyl(1-allyl-3-arylprop-2-yn-1-yl)- and dialkyl(1-allyl-3-alkenylprop-2-yn-1-yl)amines. Here, the allyl group acts as migrating group, and 3-aryl- or 3-alkenylprop-2-yn-1-yl, as receiving one. The yields of the Stevens rearrangement products fall down as the alkyl chain becomes longer, as well as with introduction of a methyl group into the meta or para position of the aromatic ring.

  DOI：

  10.1134/s1070428006120025
• 作为产物：
  描述：

  哌啶 、 聚合甲醛 、 2-甲基-1-丁烯-3-炔 在 三氯化铁 作用下， 以 1,4-二氧六环 为溶剂， 反应 70.0h， 以62%的产率得到1-(3-isopropenylprop-2-yn-1-yl)piperidine
  参考文献：
  名称：

  Synthesis of dialkyl(1-allyl-3-arylprop-2-yn-1-yl)-and dialkyl(1-allyl-3-alkenylprop-2-yn-1-yl)amines by the stevens rearrangement

  摘要：

  The Stevens rearrangement of dialkyl(allyl)(3-arylprop-2-yn-1-yl)- and dialkyl(allyl)(3-alkenylprop-2-yn-1-yl)ammonium bromides gave dialkyl(1-allyl-3-arylprop-2-yn-1-yl)- and dialkyl(1-allyl-3-alkenylprop-2-yn-1-yl)amines. Here, the allyl group acts as migrating group, and 3-aryl- or 3-alkenylprop-2-yn-1-yl, as receiving one. The yields of the Stevens rearrangement products fall down as the alkyl chain becomes longer, as well as with introduction of a methyl group into the meta or para position of the aromatic ring.

  DOI：

  10.1134/s1070428006120025

文献信息

• Cyclization of dialkylpropyn-1-yl(allyl)(3-isopropenylpropyn-2-yl)ammonium bromides and water-base cleavage of 2,2-dialkyl-5-methyl-2,6,7,7<i>a</i>-tetrahydro-1<i>h</i>-isoindolium and 2,2-dialkyl-5-methylisoindolinium bromides
  作者：Emma H. Chukhajian、Martiros K. Nalbandyan、Hasmik R. Gevorkyan、Eliza H. Chukhajian、Henrik A. Panosyan、Armen G. Ayvazyan、Rafael A. Tamazyan

  DOI：10.1002/jhet.5570450309

  日期：2008.5

  yn-2-yl)ammonium bromides under base-catalyzed condition instantly undergo intramolecular cyclization. The cyclization of dialkylpropyn-1-yl(3-isopropenylpropyn-2-yl)ammonium bromides leads to the formation of 2,2-dialkyl-5-methylisoindolinium salts. In case of allyl analogs, instead of the expected 2,2-dialkyl-6-methyl-3a,4-dihydroisoindolinium salts their isomeric forms - 2,2-dialkyl-5-methyl-2,6

  在碱催化条件下，二烷基丙炔-1-基（或烯丙基）（3-异丙烯基丙炔-2-基）溴化铵立即经历分子内环化。二烷基丙炔-1-基（3-异丙烯基丙炔-2-基）溴化铵的环化导致形成2，2-二烷基-5-甲基异吲哚鎓盐。在烯丙基类似物，而不是预期的2,2-二烷基-6-甲基- 3的情况下一个，4- dihydroisoindolinium盐及其异构体形式- 2,2-二烷基-5-甲基2,6,7,7一-获得四氢-1 H-异吲哚溴化物。在碱性介质中，它们被转化为二氢异吲哚鎓盐，其在两个方向（1,2,1,6）上的裂解导致异构的二烷基-1,4-二甲基-和2,4-二甲基苄基胺的混合物。
• Base catalyzed intramolecular cyclization of dialkycrotyl(3-alkenylpropyn-2-yl)ammonium salts and aqueous base fission of 2,2-dialkyl-4-methyl-and 2,2-dialkyl-4,6-dimethyl-2,6,7,7a-tetrahydro-1H-isoindolium bromides
  作者：E. O. Chukhajian、M. K. Nalbandyan、A. R. Gevorkyan、K. G. Shakhatuni、G. A. Panosyan

  DOI：10.1007/s10593-008-0090-9

  日期：2008.6

  Cyclization of dimethylcrotyl(3-vinyl-or-3-isopropenylpropyn-2-yl)ammonium bromides in the presence of base gave a mixture of the isomeric 2,2-dialkyl-4-methyl-and 2,2-dialkyl-4,6-dimethyl-2,6,7,7a-tetrahydro-1H-isoindolium bromides. Basic fission of the salts obtained at increased temperature gave a mixture of the isomeric N,N-disubstituted di-and trimethylbenzylamines whose structures were confirmed by their IR, H-1 NMR, and C-13 NMR spectra.
• Cyclization of dialkyl(4-hydroxy-2-butynyl)-(3 isopropenylpropargyl)ammonium salts and intramolecular recyclization of the resultant products
  作者：E. O. Chukhajian、M. K. Nalbandyan、G. A. Panosyan

  DOI：10.1007/s10593-007-0061-6

  日期：2007.4
• Synthesis of dialkyl(1-allyl-3-arylprop-2-yn-1-yl)-and dialkyl(1-allyl-3-alkenylprop-2-yn-1-yl)amines by the stevens rearrangement
  作者：E. O. Chukhadzhyan、A. R. Gevorkyan、M. K. Nalbandyan

  DOI：10.1134/s1070428006120025

  日期：2006.12

  The Stevens rearrangement of dialkyl(allyl)(3-arylprop-2-yn-1-yl)- and dialkyl(allyl)(3-alkenylprop-2-yn-1-yl)ammonium bromides gave dialkyl(1-allyl-3-arylprop-2-yn-1-yl)- and dialkyl(1-allyl-3-alkenylprop-2-yn-1-yl)amines. Here, the allyl group acts as migrating group, and 3-aryl- or 3-alkenylprop-2-yn-1-yl, as receiving one. The yields of the Stevens rearrangement products fall down as the alkyl chain becomes longer, as well as with introduction of a methyl group into the meta or para position of the aromatic ring.