(3,4-dihydro-2H-pyrrol-5-yl)(phenyl)methanone

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: (3,4-dihydro-2H-pyrrol-5-yl)(phenyl)methanone
• 英文别名: 2-Benzoyl-1-pyrroline；3,4-dihydro-2H-pyrrol-5-yl(phenyl)methanone
• 化学式: C₁₁H₁₁NO
• 分子量: 173.214
• InChiKey: QEXXDGJSKFWCCL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.2
• 重原子数：
  13
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  29.4
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  5-溴戊酸 在 吡啶 、 N-溴代丁二酰亚胺(NBS) 、 草酰氯 、 18-冠醚-6 、 硫酸 、 potassium tert-butylate 、 苄基三乙基氯化铵 、 sodium hydride 、 potassium carbonate 、 sodium hydroxide 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 、 水 、 1,2-二氯乙烷 、 N,N-二甲基甲酰胺 、 甲苯 、 乙腈 为溶剂， 反应 21.75h， 生成 (3,4-dihydro-2H-pyrrol-5-yl)(phenyl)methanone
  参考文献：
  名称：

  N-烷氧基内酰胺的顺序亲核化/环收缩重排

  摘要：

  开发了一种α-溴N-烷氧基内酰胺与有机金属试剂的亲核加成/环收缩重排，可有效地获得结合了各种C（sp 2）单元（如芳基，杂芳基和烯基）的α-酰基吡咯烷。顺序反应通过使用亲核加成形成五元螯合物，然后通过形成N，O-半缩醛以良好的收率和宽的底物范围进行环收缩而进行。此外，描述了使用手性N-烷氧基内酰胺进行非对映选择性反应的初步结果。

  DOI：

  10.1021/acs.orglett.0c03821

文献信息

• A Commercially Available and User-Friendly Catalyst for Hydroamination Reactions under Technical Conditions
  作者：Benjamin Zelenay、Peter Munton、Xiaojie Tian、Silvia Díez-González

  DOI：10.1002/ejoc.201900701

  日期：2019.8.7

  The activity of a simple, commercially available copper salt, [Cu(NCMe)4](BF4) in intramolecular hydroamination reactions of alkynes and allenes is presented. Reactions were successfully carried out in technical acetonitrile in the presence of air. While attempts of alkene hydroamination failed, this catalysts was also found active in intermolecular aza-Michael reactions.

  介绍了一种简单的市售铜盐 [Cu(NCMe)4](BF4) 在炔烃和丙二烯的分子内加氢胺化反应中的活性。在空气存在下，在工业乙腈中成功进行了反应。虽然烯烃加氢胺化的尝试失败了，但也发现这种催化剂在分子间氮杂-迈克尔反应中具有活性。
• Iron-Catalyzed Acyl Migration of Tertiary α-Azidyl Ketones: Synthetic Approach toward Enamides and Isoquinolones
  作者：Tonghao Yang、Xing Fan、Xiaopeng Zhao、Wei Yu

  DOI：10.1021/acs.orglett.8b00409

  日期：2018.4.6

  transformed into enamides by treatment with FeBr2 at elevated temperature in DMF. The reaction proceeds via 1,2-benzoyl migration from α-carbon to the nitrogen atom, accompanied by expulsion of a nitrogen molecule. This protocol is suitable for the synthesis of N-(cyclopent-1-en-1-yl)benzamides, N-(cyclohex-1-en-1-yl)benzamides, and N-benzoyl-α-methyl enamines and provides a convenient approach toward isoquinolones

  本文报道，在较高的温度下，通过在DMF中用FeBr 2处理，可以将叔α-叠氮基苯基酮转化为酰胺。该反应通过从α-碳到氮原子的1，2-苯甲酰基迁移而伴随着氮分子的排出而进行。该方案适用于合成N-（环戊-1-烯-1-基）苯甲酰胺，N-（环己-1-烯-1-基）苯甲酰胺和N-苯甲酰基-α-甲基烯胺。异喹诺酮类的简便治疗方法。
• Quantitation of Important Roast-Smelling Odorants in Popcorn by Stable Isotope Dilution Assays and Model Studies on Flavor Formation during Popping
  作者：Peter Schieberle

  DOI：10.1021/jf00057a024

  日期：1995.9

  Stable isotope dilution assays were developed for the quantitation of the roast-smelling popcorn odorants, 2-acetyl-tetrahydropyridine (ACTPY) and 2-propionyl-1-pyrroline (PPY). Both and, in addition, the two further roast-aroma compounds, a-acetyl-l-pyrroline (ACPY) and acetylpyrazine, were quantified in different popcorn samples. In fresh hot-air popped corn, ACTPY showed the highest concentration (437 mu g/kg), followed by ACPY (24 mu g/kg) which were established as the key contributors to the roasty popcorn odor. During storage of a popcorn sample for seven days in a sealed polyethylene bag, the concentrations of ACTPY, ACPY, and PPY decreased to about one third. Model studies using aqueous maize extracts and distinct precursor compounds revealed the pair proline/fructose as the most effective precursor system in ACTPY formation, while the pair 1-pyrroline/2-oxopropanal was most effective in the generation of ACPY. A reaction scheme suggesting that ACPY is formed by an ''acylation'' of the intermediate 1-pyrroline by 2-oxopropanal is discussed.
• Intramolecular Hydroamination of Aminoalkynes with Silver−Phenanthroline Catalysts
  作者：Jeffrey M. Carney、Patrick J. Donoghue、William M. Wuest、Olaf Wiest、Paul Helquist

  DOI：10.1021/ol801458g

  日期：2008.9.1

  Intramolecular hydroamination of several aminoalkynes catalyzed by silver-phenanthroline complexes is reported. This catalyst system complements previous protocols by employing air- and moisture-stable complexes without compromising activity or reaction control. Some of the hydroamination products are subject to a useful aerobic oxidation. Silver-phenanthroline complexes have successfully demonstrated efficacy in the desymmetrization of a prochiral diyne.
• Sequential Nucleophilic Arylation/Ring-Contractive Rearrangement of <i>N</i>-Alkoxylactams
  作者：Norihiko Takeda、Yukiko Kobori、Kohei Okamura、Motohiro Yasui、Masafumi Ueda

  DOI：10.1021/acs.orglett.0c03821

  日期：2020.12.18

  A nucleophilic addition/ring-contractive rearrangement of α-bromo N-alkoxylactams with organometallic reagents was developed, providing an efficient access to α-acylpyrrolidines incorporating various C(sp2) units such as aryl, heteroaryl, and alkenyl groups. The sequential reaction proceeds through a five-membered chelate formation using nucleophilic addition followed by ring contraction via the formation

  开发了一种α-溴N-烷氧基内酰胺与有机金属试剂的亲核加成/环收缩重排，可有效地获得结合了各种C（sp 2）单元（如芳基，杂芳基和烯基）的α-酰基吡咯烷。顺序反应通过使用亲核加成形成五元螯合物，然后通过形成N，O-半缩醛以良好的收率和宽的底物范围进行环收缩而进行。此外，描述了使用手性N-烷氧基内酰胺进行非对映选择性反应的初步结果。