Phthalimido-keten | 69177-79-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 异吲哚及其衍生物
• 英文名称: Phthalimido-keten
• 英文别名: Phthalimidoketene
• CAS: 69177-79-3
• 化学式: C₁₀H₅NO₃
• 分子量: 187.155
• InChiKey: GTISCRIUUOAYDS-UHFFFAOYSA-N

物化性质

• 沸点：
  301.7±35.0 °C(Predicted)
• 密度：
  1.505±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  14
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  54.4
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  Phthalimido-keten 在 palladium diacetate 、 Ti₂CO₃ 、 三苯基膦 作用下， 以 乙腈 、 苯 为溶剂， 反应 20.0h， 生成 2-((1R,9bS)-4-Methylene-2-oxo-1,2,3,4,5,9b-hexahydro-2a-aza-benzo[a]cyclobuta[c]cyclohepten-1-yl)-isoindole-1,3-dione
  参考文献：
  名称：

  Sequential and cascade [2+2] — cycloaddition-palladium catalysed cyclisation: Bicyclic β-lactams

  摘要：

  Sequential and cascade ketene-imine [2+2]-cycloaddition-palladium catalysed cyclisation reactions occur in good yield. Racemic and homochiral examples incorporating a range of aromatic and heteroaromatic rings are reported.

  DOI：

  10.1016/0040-4039(95)01910-a
• 作为产物：
  描述：

  邻苯二甲酰甘氨酸 在 氯化亚砜 、 calcium chloride 作用下， 以 苯 为溶剂， 反应 3.0h， 生成 Phthalimido-keten
  参考文献：
  名称：

  多种功能化 2,3-烯丙酸酯的合成和细胞毒活性

  摘要：

  摘要 合成了一系列新的功能化烯丙酸酯，并研究了它们对肿瘤细胞系（HepG2 和 Jurkat）和正常来源细胞（HEK293）的细胞毒作用。含有二萜的丙二烯化合物显示出最高的细胞毒性作用，这可归因于具有潜在抗肿瘤活性的有前途的物质。

  DOI：

  10.1134/s1068162020010057

文献信息

• Chemical modification of sulfazecin. Synthesis of 4-methoxycarbonyl-2-azetidinone-1-sulfonic acid derivatives.
  作者：SHOJI KISHIMOTO、MICHIYUKI SENDAI、MITSUMI TOMIMOTO、SHOHEI HASHIGUCHI、TAISUKE MATSUO、MICHIHIKO OCHIAI

  DOI：10.1248/cpb.32.2646

  日期：——

  In the course of the chemical modification of sulfazecin, 3-[2-(2-aminothiazol-4-yl)-(Z)-2-(substituted oxyimino) acetamido]-4-methoxycarbonyl-2-azetidinone-1-sulfonic acids were synthesized starting from cis-1-(2, 4-dimethoxybenzyl)-4-methoxycarbonyl-3-phthalimido-2-azetidinone (2). These new 4-substituted derivatives showed more potent antimicrobial activities against gram-negative bacteria than did the corresponding 4-unsubstituted compounds, and the derivatives having 3, 4-cis stereochemistry were more active than the trans isomers, especially against P. aeruginosa and some β-lactamase-producing bacteria. The reported procedure for the cycloaddition reaction used to prepare 2 was investigated in detail ; by the use of a 20% excess of triethylamine, 2 was easily obtained in the yield of 72% as colorless crystals. A possible intermediate of β-lactam formation in this cycloaddition reaction, an acyl iminium salt (6), was isolated as crystals and converted into β-lactams by treatment with 1, 8-diazabicyclo [5. 4. 0]-7-undecene.

  在磺扎西丁的化学修饰过程中，从顺式-1-(2,4-二甲氧基苄基)-4-甲氧羰基-3-酞酰亚胺基-2-氮杂环丁酮(2)出发，合成了3-[2-(2-氨基噻唑-4-基)-(Z)-2-(取代氧亚胺基)乙酰胺基]-4-甲氧羰基-2-氮杂环丁酮-1-磺酸。这些新的4-取代衍生物对革兰氏阴性菌的抗菌活性比相应的4-未取代化合物更强，其中具有3,4-顺式立体化学结构的衍生物比反式异构体更活跃，尤其对铜绿假单胞菌和一些产生β-内酰胺酶的细菌更为有效。研究了用于制备2的环加成反应的报道程序;通过使用20%过量的三乙胺，可以很容易地以72%的产率得到无色晶体2。在这种环加成反应中形成β-内酰胺的可能中间体——酰基亚胺盐(6)被分离为晶体，并通过与1,8-二氮杂双环[5.4.0]-7-十一碳烯处理转化为β-内酰胺。
• Microwave-Induced Bismuth Nitrate-Catalyzed Michael Reaction of 3-Amino β-Lactams with Enones
  作者：Ram Naresh Yadav、Ashok Kumar Srivastava、Bimal Krishna Banik

  DOI：10.14233/ajchem.2020.22168

  日期：2020.1.15

  Microwave-induced bismuth nitrate-catalyzed reaction of 3-amino β-lactams with unsaturated ketones is performed in order to obtain substituted amino β-lactams. Amino β-lactams were obtained through the strategy of [2+2] ketene-imine cycloaddition followed by deprotection of phthalimido β-lactams with ethylene diamine.

  使用微波诱导的铋硝酸盐催化剂反应，将3-氨基β-内酰胺与不饱和酮反应，以获得取代的氨基β-内酰胺。氨基β-内酰胺是通过[2+2]烯酮-亚胺环加成策略获得，然后用乙二胺去保护邻苯二甲酰亚胺β-内酰胺。
• Synthesis and Cytotoxic Activity of a Number of Functionalized 2,3-Allenoates
  作者：R. N. Malikova、I. M. Sakhautdinov、M. A. Maksimova、U. Sh. Kuzmina、Yu. V. Vakhitova、M. S. Yunusov

  DOI：10.1134/s1068162020010057

  日期：2020.1

  functionalized allenoates has been synthesized, and their cytotoxic effect has been studied against the tumor cell line (HepG2 and Jurkat) and the normal origin cells (HEK293). The highest cytotoxic effect has been shown for diterpene-containing allenic compounds, which can be attributed to promising substances with potential antitumor activity.

  摘要 合成了一系列新的功能化烯丙酸酯，并研究了它们对肿瘤细胞系（HepG2 和 Jurkat）和正常来源细胞（HEK293）的细胞毒作用。含有二萜的丙二烯化合物显示出最高的细胞毒性作用，这可归因于具有潜在抗肿瘤活性的有前途的物质。
• 1,4-di-(4-methylthiophenyl)-3-phtaloylazetidine-2-one and the derivatives thereof
  申请人：Universite De Nantes

  公开号：US10457665B2

  公开（公告）日：2019-10-29

  The present invention relates to a compound with formula (I) or a salt and/or a pharmaceutically acceptable solvate thereof, the method for preparing same as well as the uses thereof, in particular the therapeutic use thereof, mainly in the treatment of diseases associated with a hyperactivity of the endocannabinoid system.

  本发明涉及一种式（I）化合物或其盐和/或其药学上可接受的溶液、其制备方法及其用途，特别是其治疗用途，主要用于治疗与内源性大麻素系统亢进有关的疾病。
• Maier, Guenther; Reisenauer, Hans Peter; Sayrac, Tugmac, Chemische Berichte, 1982, vol. 115, # 6, p. 2192 - 2201
  作者：Maier, Guenther、Reisenauer, Hans Peter、Sayrac, Tugmac

  DOI：——

  日期：——