(3R,4R)-1,3,4-triphenyl-2-azetidinone | 434283-66-6

• 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: (3R,4R)-1,3,4-triphenyl-2-azetidinone
• 英文别名: (3R,4R)-1,3,4-triphenylazetidin-2-one
• CAS: 434283-66-6
• 化学式: C₂₁H₁₇NO
• 分子量: 299.372
• InChiKey: IUQCUELHHDRDJI-UXHICEINSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.2
• 重原子数：
  23
• 可旋转键数：
  3
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.1
• 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：

  (3R,4R)-1,3,4-triphenyl-2-azetidinone 以28%的产率得到
  参考文献：
  名称：

  SHERADSKY T.; ZBAIDA D., J. ORG. CHEM., 1980, 45, NO 11, 2165-2169

  摘要：

  DOI：
• 作为产物：
  描述：

  2,3,5-triphenyl-4-thiazolone 以12%的产率得到
  参考文献：
  名称：

  SHERADSKY T.; ZBAIDA D., J. ORG. CHEM., 1980, 45, NO 11, 2165-2169

  摘要：

  DOI：

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。
• Studies on the Enantioselective Kinugasa Reaction: Efficient Synthesis of β-Lactams Catalyzed by<i>N</i>-PINAP/CuX Complexes
  作者：Karol Wolosewicz、Michał Michalak、Jakub Adamek、Bartłomiej Furman

  DOI：10.1002/ejoc.201600050

  日期：2016.4

  enantioselective Kinugasa reactions between acyclic and, for the first time, cyclic nitrones and terminal alkynes are described herein. A catalytic amount of the readily available PINAP/CuX complexes, generated in situ, efficiently catalyzed the Kinugasa reactions, leading to a series of β-lactams with good enantioselectivities and moderate diastereoselectivities and yields. A broad range of nitrones and terminal

  本文首次描述了无环与环状硝酮和末端炔烃之间的催化对映选择性 Kinugasa 反应。催化量的容易获得的 PINAP/CuX 复合物，原位生成，有效地催化了衣笠反应，产生了一系列具有良好对映选择性和中等非对映选择性和产率的 β-内酰胺。在反应条件下可以耐受广泛的硝酮和末端炔烃，包括很少报道的烷基取代炔烃。Further investigations proved that the PINAP/CuX catalytic system enabled the synthesis of monobactams on the gram scale (without loss of stereoselectivity and yield) and also both enantiomers by the appropriate choice of readily available atropisomeric
• Cu(I)/Bis(azaferrocene)-Catalyzed Enantioselective Synthesis of β-Lactams via Couplings of Alkynes with Nitrones
  作者：Michael M.-C. Lo、Gregory C. Fu

  DOI：10.1021/ja025833z

  日期：2002.5.1

  As a consequence of the wide-ranging significance of beta-lactams (e.g., use as drugs and as chiral building blocks), a great deal of effort has been dedicated to the development of methods for their stereoselective synthesis. Although considerable progress has been achieved, nearly all of the approaches that have been described are based on the use of chiral precursors; direct catalytic enantioselective routes to beta-lactams are rare as well as limited in scope. In this communication, we establish that, using a new C2-symmetric planar-chiral bis(azaferrocene) ligand, we can generate beta-lactams with very good enantiomeric excess and cis diastereoselection via catalytic enantioselective Kinugasa reactions (couplings of alkynes with nitrones). Appealing attributes of this process include the ready availability of the starting materials, the functional-group tolerance of the reaction, and the convergency of the approach.