1-(pyrrolidin-1-yl)hept-2-yn-1-one | 50779-56-1

• 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-(pyrrolidin-1-yl)hept-2-yn-1-one
• 英文别名: 1-Pyrrolidin-1-ylhept-2-yn-1-one
• CAS: 50779-56-1
• 化学式: C₁₁H₁₇NO
• 分子量: 179.262
• InChiKey: PIKQONMERVWEDI-UHFFFAOYSA-N

物化性质

• 沸点：
  135-136 °C(Press: 0.1 Torr)
• 密度：
  1.013±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  13
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.73
• 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-(pyrrolidin-1-yl)hept-2-yn-1-one 在 [RuH2(PPh3)4] 三丁基膦 作用下， 以 甲苯 为溶剂， 反应 48.0h， 以92%的产率得到N-(2E,4E-heptadienoyl)-pyrrolidine
  参考文献：
  名称：

  A convenient stereoselective synthesis of conjugated dienoic esters and amides

  摘要：

  DOI：

  10.1016/s0040-4020(01)85458-2
• 作为产物：
  描述：

  2-庚炔酸 在 草酰氯 作用下， 以 乙醚 为溶剂， 反应 0.67h， 生成 1-(pyrrolidin-1-yl)hept-2-yn-1-one
  参考文献：
  名称：

  A convenient stereoselective synthesis of conjugated dienoic esters and amides

  摘要：

  DOI：

  10.1016/s0040-4020(01)85458-2

文献信息

• Bifunctional Phosphine Ligand Enabled Gold‐Catalyzed Alkynamide Cycloisomerization: Access to Electron‐Rich 2‐Aminofurans and Their Diels–Alder Adducts
  作者：Xingguang Li、Xu Ma、Zhixun Wang、Pei‐Nian Liu、Liming Zhang

  DOI：10.1002/anie.201908598

  日期：2019.11.25

  By using biphenyl-2-ylphosphines functionalized with a remote tertiary amino group as a ligand, readily available acetylenic amides are directly converted into 2-aminofurans devoid of any electron-withdrawing and hence deactivating/stabilizing substituents. These highly electron-rich furans have rarely been prepared, let alone applied in synthesis, because of their high reactivities and low stabilities

  通过使用被远端叔氨基官能化的联苯-2-基膦作为配体，容易获得的炔属酰胺被直接转化为2-氨基呋喃，而没有任何吸电子和失活/稳定的取代基。这些高电子富集的呋喃很少制备，更不用说用于合成了，因为它们具有与呋喃环的富电子性质相关的高反应性和低稳定性。在这项工作中，这些反应性呋喃可以顺利进行原位分子间Diels-Alder反应，以提供高度官能化/取代的苯胺产品，或通过分子内化合物以高收率或优异的收率提供咔唑-4-羧酸酯。
• Thiuram Disulfide Mediated Cu-Catalyzed Amidation of Terminal Alkynes: An Efficient Synthesis of Alkynyl Amides
  作者：Sourav Mondal、Soumya Mondal、Amit Saha

  DOI：10.1021/acs.joc.3c01961

  日期：2024.2.16

  Terminal alkynes undergo a CO-free aminocarbonylation reaction mediated by thiuram disulfides. Thiuram disulfide acts as the source of the carbamoyl group in the amidation of terminal alkynes in the presence of copper-based reagent and catalyst. A series of alkynyl amides has been prepared with several structural variations following the current one-pot two-step protocol. The reaction proceeds through

  末端炔烃经历由二硫化秋兰姆介导的无CO氨基羰基化反应。在铜基试剂和催化剂存在下，二硫化秋兰姆在末端炔烃的酰胺化反应中充当氨基甲酰基的来源。按照当前的一锅两步方案，制备了一系列具有多种结构变化的炔基酰胺。该反应通过混合二硫化物中间体进行，该中间体已通过单晶 XRD 分析进行分离和表征。
• Addition of zinc homoenolates to acetylenic esters and amides: a formal [3 + 2] cycloaddition
  作者：Michael T. Crimmins、Philippe G. Nantermet、B. Wesley Trotter、Isabelle M. Vallin、Paul S. Watson、Lynne A. McKerlie、Tracy L. Reinhold、Adrian Wai Hing Cheung、Katherine A. Stetson

  DOI：10.1021/jo00057a013

  日期：1993.2

  The copper-catalyzed conjugate addition-cycloacylation reaction of zinc homoenolates with acetylenic esters or acetylenic amides is described. The zinc homoenolate is prepared from [(ethoxycyclopropyl)oxy]trimethylsilane and zinc chloride in ether. Addition of an acetylenic amide or ester provides 2-carboxamido-or 2-carboalkoxy-3-alkylcyclopent-2-en-1-ones in good to excellent yields. The reaction can be carried out in the presence of a variety of sensitive functional groups including epoxides, alpha,beta-unsaturated esters, acetals, silyl ethers, and furans.
• Alkoxy-Directed Insertion of Carbon-Carbon Double Bonds into Tantalum-Alkyne Complexes. Chemo- and Stereoslective Addition of Alkenyl Groups to Olefins
  作者：Kazuhiko Takai、Masashi Yamada、Hidetoshi Odaka、Kiitiro Utimoto

  DOI：10.1021/jo00099a004

  日期：1994.10

  Chemo- and stereoselective addition of alkenyl groups at terminal positions of olefins is accomplished by the reaction between tantalum-alkyne complexes and terminal olefins having adjacent hydroxyl groups.
• Stereoselective synthesis of trisubstituted .alpha.,.beta.-unsaturated esters and amides via reactions of tantalum-alkyne complexes derived from acetylenic esters and amides with carbonyl compounds
  作者：Kazuhiko Takai、Makoto Tezuka、Kiitiro Utimoto

  DOI：10.1021/jo00021a005

  日期：1991.10

  Treatment of acetylenic esters with low-valent tantalum (TaCl5 and Zn) in DME and benzene produces tantalum-alkyne complexes (not isolated), which react with carbonyl compounds regioselectively at the alpha-position of the esters to give Z isomers of trisubstituted alpha,beta-unsaturated esters in a stereoselective manner. In contrast, tantalum-alkyne complexes derived from acetylenic amides react with carbonyl compounds at the beta-position of the amides predominantly.