3-pyrrolidino-1-phenyl-2-buten-1-one | 30736-22-2

• 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-pyrrolidino-1-phenyl-2-buten-1-one
• 英文别名: 3-Pyrrolidino-1-phenyl-2-buten-1-on；1-phenyl-3-(1-pyrrolidinyl)-2-butene-1-one；1-phenyl-3-pyrrolidin-1-yl-but-2-en-1-one；1-phenyl-3-pyrrolidin-1-ylbut-2-en-1-one
• CAS: 30736-22-2
• 化学式: C₁₄H₁₇NO
• 分子量: 215.295
• InChiKey: YGOUMBZNIBHPBM-UHFFFAOYSA-N

物化性质

• 熔点：
  157-158 °C
• 沸点：
  329.0±25.0 °C(Predicted)
• 密度：
  1.077±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  16
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  20.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  3-pyrrolidino-1-phenyl-2-buten-1-one 在 Selectfluor 、 三乙胺 作用下， 以 乙腈 为溶剂， 反应 4.83h， 以58%的产率得到2,2-二氟-1-苯基-1,3-丁二酮
  参考文献：
  名称：

  Chemoenzymatic synthesis of optically active alcohol and β-amino-acid derivative containing the difluoromethylene group

  摘要：

  The bioreduction of alpha,alpha-difluorinated ketones, ethyl 2,2-difluoro-3-oxobutanoate (2a) and 2,2-difluoro-1-phenyl-1,3-butanedione (2b), with cells of recombinant Escherichia coli overproducing SCR (Saccharomyces cerevisiae carbonyl reductase from bakers' yeast) and GDH (glucose dehydrogenase from Bacillus megaterium) gave enantiomerically pure alcohols, ethyl (S)-2,2-difluoro-3-hydroxybutanoate ((S)-1a) and (S)-2,2-difluoro-3-hydroxy-1-phenyl-1-butanone ((S)-1b), respectively, in the presence of NADP(+) and glucose in buffer. The reductions of 2a and 2b proceeded completely at the substrate concentrations of 0.4 M (67 g/L) and 1.0 M (200 g/L), respectively. The opposite enantiomers (R)-1a and (R)-1b were also produced by enzyme E039 (a mixture of carbonyl reductase and formate dehydrogenase) contained in Chiralscreen OH (Daicel Chemical Industries) in the presence of NADH and sodium formate in buffer. Enantiomerically pure (S)-1a was converted by organic synthetic methods into an a,a-difluorinated derivative of (R)-beta-aminobutyric acid (BABA) in three steps. (C) 2010 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.molcatb.2010.05.009
• 作为产物：
  描述：

  1-phenyl-3-chloro-2-buten-1-one 在 三乙胺 作用下， 以 甲醇 为溶剂， 反应 2.0h， 生成 3-pyrrolidino-1-phenyl-2-buten-1-one
  参考文献：
  名称：

  Kashima, Choji; Tajima, Tadakuni; Omote, Yoshimori, Journal of Heterocyclic Chemistry, 1984, vol. 21, p. 171 - 176

  摘要：

  DOI：

文献信息

• Interaction of push–pull tert-enamines with phenylglyoxal
  作者：Dmitry A. Sibgatulin、Dmitry M. Volochnyuk、Aleksander N. Kostyuk、Sergey P. Ivonin、Andriy V. Lapandin

  DOI：10.1007/s00706-009-0110-1

  日期：2009.6

  AbstractThe reaction of push–pull enamines with 1,2-biselectrophilic phenylglyoxal was investigated. Phenylglyoxal was found to react depending on the structure of the push–pull enamine, affording either a hydroxyalkylation product at the methyl group or the cyclic product via participation of the methyl group and the β-carbon of the enamine. Graphical abstract

  摘要研究了推挽式烯胺与1,2-双亲电子苯基乙二醛的反应。发现苯乙二醛会根据推挽式烯胺的结构发生反应，从而通过甲基和烯胺的β-碳的参与提供甲基的羟烷基化产物或环状产物。 图形概要
• New approach to CF3-containing polysubstituted anilines: reaction of β-trifluoroacetylvinyl ethers with enamines
  作者：Dmitriy M Volochnyuk、Alexander N Kostyuk、Dmitriy A Sibgatulin、Alexander N Chernega、Alexander M Pinchuk、Andrei A Tolmachev

  DOI：10.1016/j.tet.2004.01.010

  日期：2004.3

  The reaction of β-trifluoroacetylvinyl ethers with ‘push–pull’ enamines having a methyl group at the α-position was investigated. As a result, a set of CF3-containing dialkyl anilines and their covalent hydrates were obtained. A possible reaction mechanism and the stability of the covalent hydrates obtained are discussed.

  研究了β-三氟乙酰乙烯基醚与在α位具有甲基的“推挽”烯胺的反应。结果，获得了一组含CF 3的二烷基苯胺及其共价水合物。讨论了可能的反应机理和所得共价水合物的稳定性。
• SELECTIVE SYNTHESIS OF 3,5-DISUBSTITUTED ISOXAZOLES FROM β-SUBSTITUTED ENONES AND HYDROXYLAMINE HYDROCHLORIDE IN THE PRESENCE OF VARIOUS BASES
  作者：Choji Kashima、Nobutoshi Yoshiwara、Shun-ichi Shirai、Yoshimori Omote

  DOI：10.1246/cl.1982.1455

  日期：1982.9.5

  The synthesis of two isomeric isoxazoles could be selectively controlled in the reaction of β-substituted enones with 3 species of hydroxylamine; hydroxyammonium cation (1), free hydroxylamine (2) and aminohydroxy anion (3).

  β-取代烯酮与3种羟胺反应可以选择性控制两种异构异恶唑的合成；羟铵阳离子 (1)、游离羟胺 (2) 和氨基羟基阴离子 (3)。
• Ruthenium(<scp>ii</scp>)-catalysed direct synthesis of mono-allylation products of 1,3-diketones from cinnamyl alcohols
  作者：Rajesh K. Jena、Mahesh Samanta、Mohan C. Sau、Sonali Panda、Braja N. Patra、Manish Bhattacharjee

  DOI：10.1039/d2nj01650h

  日期：——

  synthesized and structurally characterized. It crystallizes in the orthorhombic non-centrosymmetric space group P212121 and undergoes auto-resolution. The complex is an efficient catalyst for direct carbon–carbon bond-formation reactions using cinnamyl alcohols to produce enantio- and regioselective mono-allylation products of diketones in high yield. A wide range of substrates provides good to excellent

  合成了复合物[Ru( p -cymene)(dppe)Cl]PF 6 ·C 7 H 8并进行了结构表征。它在正交非中心对称空间群P 2 1 2 1 2 1中结晶并经历自动分辨。该配合物是一种有效的催化剂，用于直接碳-碳键形成反应，使用肉桂醇以高收率生产二酮的对映选择性和区域选择性单烯丙基化产物。广泛的基材提供了良好的产量。吡咯烷和乙酸添加剂的使用增加了选择性并防止了不需要的副产物。
• Corsaro, A.; Perrini, G.; Testa, M. G., Phosphorus, Sulfur and Silicon and the Related Elements, 1992, vol. 71, p. 197 - 206
  作者：Corsaro, A.、Perrini, G.、Testa, M. G.、Chiacchio, U.

  DOI：——

  日期：——