1-(4-Methoxyphenyl)-3,4-diphenylazetidin-2-on | 51527-45-8

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 二苯乙烯类
• 英文名称: 1-(4-Methoxyphenyl)-3,4-diphenylazetidin-2-on
• 英文别名: 1-(4-Methoxyphenyl)-3,4-diphenylazetidin-2-one
• CAS: 51527-45-8
• 化学式: C₂₂H₁₉NO₂
• 分子量: 329.398
• InChiKey: YCZSMQZWPLETRQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.2
• 重原子数：
  25
• 可旋转键数：
  4
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.14
• 拓扑面积：
  29.5
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  alpha-溴苯乙酸 、 4-methoxy-N-[(E)-phenylmethylidene]aniline 在 三苯基膦 作用下， 以 苯 为溶剂， 反应 18.0h， 以98%的产率得到1-(4-Methoxyphenyl)-3,4-diphenylazetidin-2-on
  参考文献：
  名称：

  Novel Method for the Synthesis of b-Lactams by the Reaction of a-Bromocarboxylic Acids with Imines Mediated by Triphenylphosphine

  摘要：

  DOI：

  10.3987/com-05-10661

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。
• 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。
• Electrogenerated NHC as an organocatalyst in the Staudinger reaction
  作者：Marta Feroci、Isabella Chiarotto、Monica Orsini、Achille Inesi

  DOI：10.1039/c002325f

  日期：——

  Electrogenerated N-heterocyclic carbene can behave as an organocatalyst in the Staudinger reaction (from imine and acyl chloride) in a very polar solvent, such as an ionic liquid.

  在极性很强的溶剂（如离子液体）中，电生成的 N-杂环碳烯在施陶丁格反应（由亚胺和酰基氯）中可用作有机催化剂。
• Manhas, Maghar S.; Chaudhary, Ashok G.; Raju, Vegesna, S., Heterocycles, 1993, vol. 35, # 2, p. 635 - 638
  作者：Manhas, Maghar S.、Chaudhary, Ashok G.、Raju, Vegesna, S.、Robb, Ernest W.、Bose, Ajay K.

  DOI：——

  日期：——
• Copper-Catalyzed Reaction of Terminal Alkynes with Nitrones. Selective Synthesis of 1-Aza-1-buten-3-yne and 2-Azetidinone Derivatives
  作者：Masahiro Miura、Masahiro Enna、Kazumi Okuro、Masakatsu Nomura

  DOI：10.1021/jo00121a018

  日期：1995.8

  Reaction of arylacetylenes with C,N-diarylnitrones using a catalyst system of CuI-dppe (dppe = 1,2-bis(diphenylphosphino)ethane) in the presence of potassium carbonate in DMF predominantly affords the corresponding 1,2,4-triaryl-1-aza- 1-buten-3-ynes in good yields. In contrast, the catalytic reaction using CuI in the presence of an excess amount of pyridine as the ligand gives 1,3,4-triaryl-2-azetidinones as the major products. The reaction with aliphatic terminal alkynes in place of arylacetylenes produces the latter products irrespective of the catalyst system used. Asymmetric induction is also observed in the reaction of phenylacetylene with alpha,N-diphenylnitrone to give 1,2,4-triphenyl-2-azetidinone in the presence of chiral bisoxazoline-type ligands.