3-azido-1,4-diphenyl-2-azetidinone | 16311-94-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 内酰胺类
• 英文名称: 3-azido-1,4-diphenyl-2-azetidinone
• 英文别名: cis-3-azido-1,4-diphenylazetidin-2-one；3-azido-1,4-diphenylazetidin-2-one；2-Azetidinone, 3-azido-1,4-diphenyl-, cis-；(3S,4R)-3-azido-1,4-diphenylazetidin-2-one
• CAS: 16311-94-7
• 化学式: C₁₅H₁₂N₄O
• 分子量: 264.286
• InChiKey: QXVSDJNBVKPWMJ-UONOGXRCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  20
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.13
• 拓扑面积：
  34.7
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  3-azido-1,4-diphenyl-2-azetidinone 在 水 作用下， 以 甲醇 、 苯 为溶剂， 反应 30.0h， 生成 3-(dimethoxyphosphorylamino)-1,4-diphenyl-2-azetidinone
  参考文献：
  名称：

  Dimukhametov, M. N.; Nuretdinov, I. A., Journal of general chemistry of the USSR, 1985, vol. 55, # 11, p. 2205 - 2209

  摘要：

  DOI：
• 作为产物：
  描述：

  3-Brom-trans-1,4-diphenylazetidin-2-on 以35%的产率得到
  参考文献：
  名称：

  MANHAS M. S.; CHAWLA H. P. S.; AMIN S. G.; BOSE A. K., SYNTHESIS , 1977, NO 6, 407-409

  摘要：

  DOI：

文献信息

• Carbocation catalyzed carboxylic acid activation in Staudinger reaction for stereoselective synthesis of β-lactams
  作者：Ankita Rai、Puneet K. Singh、Prashant Shukla、Vijai K. Rai

  DOI：10.1016/j.tetlet.2016.10.012

  日期：2016.11

  stereoselective β-lactams has been disclosed via cyclopropenium-ion-catalyzed reaction of substituted acetic acids with aldimines under mild conditions. Products are formed in high yields (86–95%) and good diastereoselectivity within 3–4 h. The new reaction is focused on the exploration of the scope of cyclopropenium-ion catalysis and introduction of a catalytic version of one-step Staudinger reaction for β-lactam

  已经公开了通过在温和的条件下环乙酸离子催化的取代乙酸与醛亚胺的合成立体选择性β-内酰胺的新策略。产物在3-4小时内以高收率（86–95％）和良好的非对映选择性形成。该新反应的重点是探索环丙烯离子催化的范围，并引入了用于一步一步Staudinger反应的催化型β-内酰胺合成方法。该反应对于一系列取代的乙酸和醛亚胺是有效的。
• A Mild and Efficient Route to 2-Azetidinones Using the Cyanuric Chloride-DMF Complex
  作者：Aliasghar Jarrahpour、Maaroof Zarei

  DOI：10.1055/s-0030-1289517

  日期：2011.10

  Efficient conversion of Schiff bases and carboxylic acids to β-lactams can be carried out at room temperature in CH2Cl2, using a cyanuric chloride-N,N-dimethyl formamide complex. The complex is easily prepared by reaction of cyanuric chloride and DMF, an inexpensive reagent, at room temperature. Optimization of conditions and comparison of yield with cyanuric chloride were performed.

  在室温下，利用氰尿酰氯-N,N-二甲基甲酰胺复合物，可以在CH2Cl2中高效地将席夫碱和羧酸转化为β-内酰胺。通过在室温下将氰尿酰氯与低成本试剂DMF反应，可以轻松制备该复合物。优化了条件并比较了产率与氰尿酰氯的结果。
• Utilization of DMF–PhCOCl Adduct as an Acid Activator in a New and Convenient Method for Preparation of β-Lactams
  作者：Maaroof Zarei

  DOI：10.1246/bcsj.20110323

  日期：2012.3.15

  An efficient one-pot synthesis of β-lactams by the reaction of imines with acetic acid derivatives in the presence of DMF and benzoyl chloride adduct, a cheap reagent, has been described. Optimizat...

  已经描述了通过亚胺与乙酸衍生物在 DMF 和苯甲酰氯加合物（一种廉价试剂）存在下的反应，高效地一锅法合成 β-内酰胺。优化...
• Reactions of Acid Chlorides/Ketenes with 2-Substituted 4,5-Dihydro-4,4-dimethyl-1,3-thiazoles: Formation of Penam Derivatives
  作者：Junxing Shi、Anthony Linden、Heinz Heimgartner

  DOI：10.1002/hlca.201300165

  日期：2013.8

  cycloaddition and led to the correspoding β‐lactam. On the other hand, acid chlorides and 4,5‐dihydro‐1,3‐thiazoles bearing an α‐H‐atom at the C(2)‐substituent underwent C(α)‐ and/or N‐addition reactions and furnished non‐β‐lactam adducts, i.e., C(α)‐ and/or N‐acylated 1,3‐thiazolidines. The attempted transformations of sulfonyl esters of exo‐6‐hydroxy penams to endo‐6‐azido penams failed, although they were

  在碱性条件下，研究了酰氯与各种2-取代的4,5-二氢-4,4-二甲基-5-（甲基硫烷基）-1,3-噻唑的加成反应。从这些添加物中获得了两种产物，β-内酰胺和非β-内酰胺加合物。当用在C（2）带有Ph取代基的4,5-二氢-1,3-噻唑进行反应时，反应通过正式的[2 + 2]环加成反应进行，并导致相应的β-内酰胺。另一方面，在C（2）取代基上带有α -H原子的酰氯和4,5-二氢-1,3-噻唑进行了C（α）和/或N加成反应，且未提供‐β-内酰胺加合物，即C（α）-和/或N-酰化的1,3-噻唑烷。尽管在相同条件下用单β-内酰胺成功，但尝试将exo -6-羟基Penam的磺酰基酯转化为内-6-叠氮基Penam的尝试失败了。
• Efficient one-pot synthesis of 2-azetidinones from acetic acid derivatives and imines using methoxymethylene-N,N-dimethyliminium salt
  作者：Aliasghar Jarrahpour、Maaroof Zarei

  DOI：10.1016/j.tet.2010.05.009

  日期：2010.7

  A cheap, versatile and convenient method for synthesis of beta-lactams using methoxymethylene-N,N-dimethyliminium salt as an acid activator in Staudinger reaction is reported. This method is used for the preparation of monocyclic, spirocyclic, N-alkyl and three-electron-withdrawing group beta-lactams. The products are obtained in good to excellent yields. (C) 2010 Elsevier Ltd. All rights reserved.