cis-1-(4-methoxyphenyl)-3-phenoxy-4-styrylazetidin-2-one-one | 108908-70-9

• 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: cis-1-(4-methoxyphenyl)-3-phenoxy-4-styrylazetidin-2-one-one
• 英文别名: 1-(4-methoxyphenyl)-3-phenoxy-4-styrylazetidin-2-one；1-p-anisyl-3-phenoxy-4-styrylazetidin-2-one
• CAS: 108908-70-9；123619-56-7；133008-22-7；133008-23-8
• 化学式: C₂₄H₂₁NO₃
• 分子量: 371.436
• InChiKey: URRDMQARXDSXES-PKTZIBPZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.57
• 重原子数：
  28.0
• 可旋转键数：
  6.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  38.77
• 氢给体数：
  0.0
• 氢受体数：
  3.0

反应信息

• 作为产物：
  描述：

  苯氧乙酸 在 六氯丙酮 、 三乙胺 、 亚磷酸三乙酯 作用下， 以 二氯甲烷 为溶剂， 反应 0.5h， 生成 cis-1-(4-methoxyphenyl)-3-phenoxy-4-styrylazetidin-2-one-one
  参考文献：
  名称：

  Arun; Govande; Deshmukh, Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 2002, vol. 41, # 4, p. 856 - 857

  摘要：

  DOI：

文献信息

• An Easy and Convenient Synthesis of β-Lactams via a One-Pot Staudinger Reaction with 4-(4,6-Dimethoxy-1,3,5-triazin-2-yl)-4-methylmorpholinium Chloride Starting from Substituted Carboxylic Acids
  作者：Maaroof Zarei

  DOI：10.2174/1570178611666141201224959

  日期：2015.1.1

  An easy and convenient direct synthesis of 2-azetidinones is described. The [2+2] cycloaddition reaction of imines and carboxylic acids using 4-(4,6-dimethoxy-1,3,5-triazin-2-yl)-4-methylmorpholinium chloride (DMTMM) has been employed to synthesize a variety of 2-azetidinones in high yields. The products were easily isolated because the byproducts are highly soluble in water.

  报道了一种简单便捷的2-氮杂环丁酮的直接合成方法。通过4-(4,6-二甲氧基-1,3,5-三嗪-2-基)-4-甲基吗啉氯盐（DMTMM）催化亚胺和羧酸的[2+2]环加成反应，实现了一系列2-氮杂环丁酮的高产率合成。产物易于分离，因为副产物在水中具有很高的溶解性。
• An improved method for the stereoselective synthesis of β-lactams from carboxylic acids and imines
  作者：Gunda I. Georg、Peter M. Mashava、Xiangming Guan

  DOI：10.1016/s0040-4039(00)74832-5

  日期：1991.1

  Carboxylic acids activated with Mukaiyama's reagent (2-chloro-N-methylpyridinium iodide) reacted with imines to produce β-lactams in good yields and with high stereoselectivity. The utilization of three equivalents of tripropylamine as the base was necessary to obtain high chemical yield and good stereoselectivity.

  用Mukaiyama试剂（2-氯-N-甲基吡啶碘鎓碘化物）活化的羧酸与亚胺反应，以高收率和高立体选择性产生β-内酰胺。为了获得高化学产率和良好的立体选择性，必须使用三当量的三丙胺作为碱。
• One-Pot Sequence Synthesis of Azetidin-2-One Using Diethyl Chlorophosphate
  作者：Maaroof Zarei

  DOI：10.3184/174751912x13282660033937

  日期：2012.2

  A simple and convenient synthesis of 2-azetidinone derivatives from the reaction of a pre-mixture of amines and aldehydes with carboxylic acids in the presence of diethyl chlorophosphate by [2+2] cycloaddition reaction is described. Separation and purification of imines as intermediates were not required. The methodology is convenient and good to excellent yields of products were obtained with simple

  描述了通过 [2+2] 环加成反应，在氯磷酸二乙酯存在下，通过胺和醛的预混合物与羧酸的反应，简单方便地合成 2-氮杂环丁酮衍生物。不需要将亚胺作为中间体进行分离和纯化。该方法操作方便，通过简单的纯化即可获得高产率的产品。
• 2,2′-Dibenzothiazolyl Disulfide: A Versatile Reagent for the Synthesis of 2-Azetidinones
  作者：S. Sharma、Seema Kanwar

  DOI：10.1055/s-2004-835628

  日期：——

  reagent that provides a convenient and efficient route for the synthesis of β-lactams from Schiff's bases and alkox/aryloxy acetic acids. The process involves the formation of thioester of the corresponding acid. Finally, condensation of titanium enolates, derived from these esters, with imines completes the synthesis of 2-azetidinones.

  已发现 2,2'-二苯并噻唑基二硫化物是一种多功能试剂，为从席夫碱和烷氧基/芳氧基乙酸合成 β-内酰胺提供了方便有效的途径。该过程涉及形成相应酸的硫酯。最后，衍生自这些酯的钛烯醇化物与亚胺的缩合完成了 2-氮杂环丁酮的合成。
• Triphosgene, an efficient acid activator for the Staudinger reaction
  作者：D Krishnaswamy、B.M Bhawal、A.R.A.S Deshmukh

  DOI：10.1016/s0040-4039(99)02074-2

  日期：2000.1

  An efficient one-step synthesis of beta-lactams by the reaction of imines with acids in the presence of triphosgene and triethylamine has been described. (C) 2000 Elsevier Science: Ltd. All rights reserved.