1-(oct-1-yn-1-yl)pyrrolidin-2-one | 332183-36-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯烷类
• 英文名称: 1-(oct-1-yn-1-yl)pyrrolidin-2-one
• 英文别名: 1-Oct-1-ynylpyrrolidin-2-one；1-oct-1-ynylpyrrolidin-2-one
• CAS: 332183-36-5
• 化学式: C₁₂H₁₉NO
• 分子量: 193.289
• InChiKey: VYGZINDDSDYUQA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  14
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.75
• 拓扑面积：
  20.3
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  1-(oct-1-yn-1-yl)pyrrolidin-2-one 在 三甲基溴硅烷 、 水 作用下， 以 二氯甲烷 为溶剂， 反应 1.33h， 以88%的产率得到(E)-1-(1-bromooct-1-enyl)pyrrolidin-2-one
  参考文献：
  名称：

  Regio- and stereospecific synthesis of (E)-α-iodoenamide moieties from ynamides through iodotrimethylsilane-mediated hydroiodation

  摘要：

  A facile approach to (E)-alpha-haloenamide moieties from ynamides using bromo- or iodotrimethylsilane is described. The simple protocol enables a regio- and stereospecific hydrohalogenation of the triple bond in gram-scale and provides a general entry for synthesis of novel enamide analogues. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2012.12.101
• 作为产物：
  描述：

  1-辛炔 在 potassium phosphate 、 N-溴代丁二酰亚胺(NBS) 、 1,10-菲罗啉 、 copper(ll) sulfate pentahydrate 、 silver nitrate 作用下， 以 丙酮 、 甲苯 为溶剂， 反应 17.0h， 生成 1-(oct-1-yn-1-yl)pyrrolidin-2-one
  参考文献：
  名称：

  Regio- and stereospecific synthesis of (E)-α-iodoenamide moieties from ynamides through iodotrimethylsilane-mediated hydroiodation

  摘要：

  A facile approach to (E)-alpha-haloenamide moieties from ynamides using bromo- or iodotrimethylsilane is described. The simple protocol enables a regio- and stereospecific hydrohalogenation of the triple bond in gram-scale and provides a general entry for synthesis of novel enamide analogues. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2012.12.101

文献信息

• Fishing with copper acetylides: Selective alkynylation of heteronucleophiles
  作者：Céline Guissart、Michel Luhmer、Gwilherm Evano

  DOI：10.1016/j.tet.2018.09.053

  日期：2018.11

  Copper acetylides are readily available and especially convenient reagents for the alkynylation of a broad range of heteronucleophiles. Upon simple activation with molecular oxygen in the presence of suitable ligands and solvents, they readily transfer their alkyne moiety at room temperature, notably yielding a variety of nitrogen- and phosphorus-substituted alkynes. We report in this manuscript an

  乙炔铜很容易获得，尤其是方便的试剂，用于广泛范围的异亲核试剂的炔基化。在合适的配体和溶剂存在下用分子氧简单活化后，它们很容易在室温下转移其炔烃部分，特别是产生各种氮和磷取代的炔烃。我们在这份手稿中报告了基于定量13对该炔基化的化学选择性的广泛研究1 H NMR分析。通过合适的配体/溶剂组合，即使存在大量过量的氮亲核试剂，各种磷基亲核试剂也可以被烷基化，并具有出色的选择性。这种化学选择性的炔基化反应可以进一步扩展到更具挑战性的氮-亲核试剂的选择性炔基化反应，进一步突出了乙炔铜作为炔化剂的合成潜力，可以选择性地“诱捕”亲核试剂而不影响其他亲核试剂。
• Efficient preparations of novel ynamides and allenamides
  作者：Lin-Li Wei、Jason A. Mulder、Hui Xiong、Craig A. Zificsak、Christopher J. Douglas、Richard P. Hsung

  DOI：10.1016/s0040-4020(00)01014-0

  日期：2001.1

  achiral allenamides, ynamides are prepared from enamides via bromination followed by base-induced elimination of the Z-bromoenamides. These ynamides and allenamides possess improved thermal stability compared to ynamines and allenamines. They can be isolated, purified, and handled with ease, and thus, should be synthetically more useful than traditional ynamines and allenamines.

  在此描述了一系列新型的酰胺和烯丙酰胺的实用合成。尽管炔丙基酰胺的碱诱导的异构化方案导致一系列手性和非手性烯丙酰胺，但是通过溴化由酰胺制备炔基酰胺，然后进行碱诱导的Z-溴烯酰胺的消除。与炔胺和烯丙胺相比，这些炔酰胺和烯丙酰胺具有改进的热稳定性。它们可以轻松分离，纯化和处理，因此在合成上应比传统的ynamines和allenamines更有用。
• Cationic polycyclization of ynamides: building up molecular complexity
  作者：Cédric Theunissen、Benoît Métayer、Morgan Lecomte、Nicolas Henry、Hwai-Chien Chan、Guillaume Compain、Phidéline Gérard、Christian Bachmann、Naima Mokhtari、Jérome Marrot、Agnès Martin-Mingot、Sébastien Thibaudeau、Gwilherm Evano

  DOI：10.1039/c7ob00850c

  日期：——

  Polycyclization reactions are among the most efficient synthetic tools for the synthesis of complex, polycyclic molecules in a single operation from simple starting materials. We report in this manuscript a full account on the discovery and development of a novel cationic polycyclization from readily available ynamides. Simple activation of these building blocks under acidic conditions enables the

  多环化反应是从单一起始原料通过一次操作合成复杂的多环分子的最有效的合成工具之一。我们在这份手稿中报告了有关从容易获得的酰胺中发现和发展新型阳离子多环化反应的完整报告。这些构件在酸性条件下的简单活化能够产生高反应性的活化的酮亚胺离子，从而引发前所未有的阳离子多环化反应，从而产生高度取代的多环氮杂环，该杂环最多具有七个稠合环和三个连续的立体中心。
• Highly Stereoselective Synthesis of Novel α-Haloenamides via a Mild and Efficient Hydrohalogenation of Ynamides
  作者：Jason A. Mulder、Kimberly C. M. Kurtz、Richard P. Hsung、Heather Coverdale、Michael O. Frederick、Lichun Shen、Craig A. Zificsak

  DOI：10.1021/ol0300266

  日期：2003.5.1

  A highly stereoselective preparation of novel chiral (E)-alpha-haloenamides under mild conditions utilizing magnesium halide salts is described. This unexpected mild and efficient hydrohalogenation reaction highlights another synthetic utility of ynamides.
• Regio- and stereospecific synthesis of (E)-α-iodoenamide moieties from ynamides through iodotrimethylsilane-mediated hydroiodation
  作者：Akihiro H. Sato、Kazuhiro Ohashi、Tetsuo Iwasawa

  DOI：10.1016/j.tetlet.2012.12.101

  日期：2013.3

  A facile approach to (E)-alpha-haloenamide moieties from ynamides using bromo- or iodotrimethylsilane is described. The simple protocol enables a regio- and stereospecific hydrohalogenation of the triple bond in gram-scale and provides a general entry for synthesis of novel enamide analogues. (C) 2012 Elsevier Ltd. All rights reserved.