(3R,4S)-1,3-二苯基-4-(对甲苯基)氮杂环丁烷-2-酮 | 62500-28-1

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 二苯乙烯类
• 中文名称: (3R,4S)-1,3-二苯基-4-(对甲苯基)氮杂环丁烷-2-酮
• 英文名称: 1,3r-diphenyl-4c-p-tolyl-azetidin-2-one
• 英文别名: 1,3r-Diphenyl-4c-p-tolyl-azetidin-2-on；2-Azetidinone, 4-(4-methylphenyl)-1,3-diphenyl-, cis-；(3S,4S)-4-(4-methylphenyl)-1,3-diphenylazetidin-2-one
• CAS: 62500-28-1
• 化学式: C₂₂H₁₉NO
• 分子量: 313.399
• InChiKey: DYKMEOLGLOATGB-LEWJYISDSA-N

物化性质

• 熔点：
  142-143 °C
• 沸点：
  525.3±50.0 °C(Predicted)
• 密度：
  1.172±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.6
• 重原子数：
  24
• 可旋转键数：
  3
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.14
• 拓扑面积：
  20.3
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为产物：
  描述：

  3,5-Diphenyl-2-p-tolyl-thiazolidin-4-one 在 镍 作用下， 以 乙醇 、 水 为溶剂， 反应 0.03h， 以80%的产率得到(3R,4S)-1,3-二苯基-4-(对甲苯基)氮杂环丁烷-2-酮
  参考文献：
  名称：

  Reductive ring contraction of mesoionic thiazol-4-ones to azetidin-2-ones

  摘要：

  DOI：

  10.1021/jo01299a026

文献信息

• Chiral tris(oxazoline)/Cu(ii) catalyzed coupling of terminal alkynes and nitronesElectronic supplementary information (ESI) available: experimental. See http://www.rsc.org/suppdata/cc/b3/b306653c/
  作者：Meng-Chun Ye、Jian Zhou、Zheng-Zheng Huang、Yong Tang

  DOI：10.1039/b306653c

  日期：——

  Novel chiral iPr-tris(oxazoline)/Cu(ClO4)2 x 6H2O catalyzed coupling of terminal acetylenes and nitrones to afford cis-disubstituted beta-lactams is described; the choice of base proves essential to both the diastereoselectivity and the enantioselectivity.

  描述了新颖的手性iPr-三（恶唑啉）/ Cu（ClO4）2 x 6H2O催化的末端乙炔和硝酮的偶联，得到顺式二取代的β-内酰胺。碱的选择被证明对非对映选择性和对映选择性都是必不可少的。
• Trisoxazoline/Cu(II)-Promoted Kinugasa Reaction. Enantioselective Synthesis of <i>β</i>-Lactams
  作者：Meng-Chun Ye、Jian Zhou、Yong Tang

  DOI：10.1021/jo0602874

  日期：2006.4.1

  precursor for the first time in the Kinugasa reaction, and this allowed the reaction to be performed under a practical and convenient condition. An appropriate base used in this reaction was essential to control both diastereoselectivity and enantioselectivity. Compared with primary and tertiary amines, secondary amines gave higher enantioselectivities. The reaction scope and limitation as well as the

  手性i催化硝基酮与末端炔烃的反应Pr-三恶唑啉2a / Cu（ClO 4）2 ·6H 2在空气气氛下，以中等至良好的产率提供了高达85％ee的β-内酰胺。非对映选择性取决于炔烃。丙炔酸酯给出反式异构体作为主要产物，而其他炔烃主要提供顺式-二取代的内酰胺。在Kinugasa反应中，铜（II）盐首次被证明是有效的催化剂前体，这使得该反应可以在实用且方便的条件下进行。在该反应中使用的合适的碱对于控制非对映选择性和对映选择性都是必不可少的。与伯胺和叔胺相比，仲胺具有更高的对映选择性。研究了反应的范围和局限性及其机理。
• Enantioselective synthesis of β-lactams via the IndaBox–Cu(II)-catalyzed Kinugasa reaction
  作者：Takao Saito、Tomohiro Kikuchi、Hiroaki Tanabe、Junichi Yahiro、Takashi Otani

  DOI：10.1016/j.tetlet.2009.06.050

  日期：2009.9

  The enantioselective Kinugasa reaction of nitrones with terminal alkynes in the presence of 20 mol % of IndaBox–Cu(OTf)2 and di-sec-butylamine (1.5 equiv) produced β-lactams with the highest level of enantiomeric excesses among the catalytic enantioselective Kinugasa reactions reported so far.

  在20 mol％IndaBox–Cu（OTf）2和二仲丁胺（1.5当量）的存在下，硝酮与末端炔烃的对映选择性Kinugasa反应生成的β-内酰胺在催化对映选择性Kinugasa中具有最高的对映体过量水平迄今已报道了反应。
• on the azetidin-2-one ring formation. A 1H NMR investigation.
  作者：Adele Bolognese、M.Vittoria Diurno、Orazio Mazzoni、Federico Giordano

  DOI：10.1016/s0040-4020(01)89743-x

  日期：1991.8

  Azetidin-2-ones were prepared by addition of phenylacetic acid chloride to substituted benzal-anilines in DMF. The effect of temperature and substituents at the benzal-anilines on the reaction mechanism was investigated, carrying out the reaction in DMF d7 in an NMR probe of a Bruker 400-MHz spectrometer, at 25 and 60-degrees-C. Proton signals, arising from two kinds of intermediates, a 2-phenyl-N-(alpha-chlorobenzyl)-acetanilide (6) and a nitrogen-charged adduct (7), suggest that two competitive mechanisms play a role in the formation of trans and cis azetidin-2-ones.
• Tris(oxazoline)/copper-catalyzed coupling of alkynes with nitrones: a highly enantioselective access to β-lactams
  作者：Jiang-Hua Chen、Sai-Hu Liao、Xiu-Li Sun、Qi Shen、Yong Tang

  DOI：10.1016/j.tet.2012.04.049

  日期：2012.6

  Chiral tris(oxazoline)/Cu(I) complexes are demonstrated as a type of efficient catalysts for the asymmetric Kinugasa reaction of terminal alkynes with C-arylnitrones, providing a highly enantio- and diastereoselective access to optically active beta-lactams. (C) 2012 Elsevier Ltd. All rights reserved.