1-pent-4-ynyl-1-piperidine-2,6-dione | 63838-16-4

• 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-pent-4-ynyl-1-piperidine-2,6-dione
• 英文别名: (1-pent-4-ynyl)piperidine-2,6-dione；N-(pent-4-ynyl)glutarimide；1-Pent-4-ynylpiperidine-2,6-dione
• CAS: 63838-16-4
• 化学式: C₁₀H₁₃NO₂
• 分子量: 179.219
• InChiKey: AGBKEZMQRDBCCW-UHFFFAOYSA-N

物化性质

• 沸点：
  110 °C(Press: 0.02 Torr)
• 密度：
  1?+-.0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.4
• 重原子数：
  13
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.6
• 拓扑面积：
  37.4
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  1-pent-4-ynyl-1-piperidine-2,6-dione 在 sodium tetrahydroborate 作用下， 以96%的产率得到6-羟基-1-戊-4-炔基-哌啶-2-酮
  参考文献：
  名称：

  1-Bromalkynes as π-nucleophiles in acyliminium ion cyclilizations. a formal synthesis of lupinine and epilupinine.

  摘要：

  The use of a 1-bromoalkyne as pi-nucleophile in the alpha-N-acyliminium ion cyclization of a glutarimide derivative results in the formation of a single bromoenol triflate 11 in triflic acid-trifluoroacetic and of a mixture (E/Z: 4/1) of bromofluoro derivatives 12a,b in HF, 11 is quantitatively converted to esters 9a,b which are also obtained after trifluoroscetic acid treatment and methanolysis. 9a,b are known precursors of lupinine and epilupinine.

  DOI：

  10.1016/s0040-4039(00)92521-8
• 作为产物：
  描述：

  戊二酰亚胺 、 5-氯戊炔 在 18-冠醚-6 、 potassium carbonate 作用下， 以 苯 为溶剂， 反应 16.0h， 以83.5%的产率得到1-pent-4-ynyl-1-piperidine-2,6-dione
  参考文献：
  名称：

  Gesson, J. P.; Jacquesy, J. C.; Rambaud, D., Bulletin de la Societe Chimique de France, 1992, # 3, p. 227 - 231

  摘要：

  DOI：

文献信息

• α-Acyliminium ion-acetylene cyclisations
  作者：H.E. Schoemeker、Tj. Boer-Terpstra、J. Dukink、W.N. Speckamp

  DOI：10.1016/0040-4020(80)85036-8

  日期：1980.1

  Cyclisation of acetylenic ethoxylactams 1b-12b leads to bridgehead nitrogen bicyclic ketones in excellent yields. The reaction is weakly acid-catalysed and proceeds at ambient temperature. The observed regioselectivity effect is discussed in terms of stability of exo vs endo vinyl cations and ring strain effects. The high yield conversion of N-(5-hexynyl)-ethoxy lactams 7b and 8b in the 5/8 and 6/8

  炔基乙氧基内酰胺1b-12b的环化可产生极高收率的桥头氮双环酮。该反应是弱酸催化的，并在环境温度下进行。根据外型对内乙烯基阳离子的稳定性和环应变效应，讨论了观察到的区域选择性效应。在5/8和6/8稠合的双环酮内酰胺7c和8c中N-（5-己炔基）-乙氧基内酰胺7b和8b的高产率转化值得特别注意。
• Synthesis of Indolizidine and Quinolizidine Derivatives via Intramolecular Cyclization of Alkynyltungsten Compounds with <i>N</i>-Acyliminium Ion
  作者：Heh-Lung Huang、Wen-Hsuan Sung、Rai-Shung Liu

  DOI：10.1021/jo010406+

  日期：2001.9.1
• Cousson, Alain; Gazeau, Catherine; Gesson, Jean-Pierre, Bulletin de la Societe Chimique de France, 1994, vol. 131, # 1, p. 95 - 104
  作者：Cousson, Alain、Gazeau, Catherine、Gesson, Jean-Pierre、Jacquesy, Jean-Claude、Rambaud, Didier、Renoux, Brigitte

  DOI：——

  日期：——
• Sonogashira/N-acyliminium ion aromatic π-cyclisation processes: access to tetra- and pentacyclic lactams
  作者：Ronald Grigg、Visuvanathar Sridharan、David A. Sykes

  DOI：10.1016/j.tet.2008.06.044

  日期：2008.9

  Application of the Sonogashira reaction of N-alkynylimides with 2-iodophenol or 2-iodo-N-tosylaniline affords 2-(N-alkylimino)-benzofurans and indoles in good yield. Selective partial reduction of the latter followed by treatment with TsOH generates N-acyliminium ions, which cyclise to afford tetra- and pentacyclic lactams in good yield. The latter are reduced to the analogous cyclic amines by BH3. (C) 2008 Elsevier Ltd. All rights reserved.
• SCHOEMAKER H. E.; BOER-TERPSTRA T.; DIJKINK J.; SPECKAMP W. N., TETRAHEDRON, 1980, 36, NO 1, 143-148
  作者：SCHOEMAKER H. E.、 BOER-TERPSTRA T.、 DIJKINK J.、 SPECKAMP W. N.

  DOI：——

  日期：——