2,5-dioxopyrrolidin-1-yl formate | 17592-54-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯烷类
• 英文名称: 2,5-dioxopyrrolidin-1-yl formate
• 英文别名: N-Formyloxysuccinimid；2,5-Pyrrolidinedione, 1-(formyloxy)-；(2,5-dioxopyrrolidin-1-yl) formate
• CAS: 17592-54-0
• 化学式: C₅H₅NO₄
• 分子量: 143.099
• InChiKey: HTHSIXDWFKZUGO-UHFFFAOYSA-N

物化性质

• 沸点：
  231.8±23.0 °C(Predicted)
• 密度：
  1.46±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -0.8
• 重原子数：
  10
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  63.7
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  1-碘-3-硝基苯 、 2,5-dioxopyrrolidin-1-yl formate 在 palladium diacetate 、 三乙胺 、 4,5-双二苯基膦-9,9-二甲基氧杂蒽 作用下， 以 2-甲基四氢呋喃 为溶剂， 反应 10.0h， 以78%的产率得到2,5-dioxopyrrolidin-1-yl 3-nitrobenzoate
  参考文献：
  名称：

  Palladium-Catalyzed Carbonylation of (Hetero)Aryl, Alkenyl and Allyl Halides by Means of N-Hydroxysuccinimidyl Formate as CO Surrogate

  摘要：

  An efficient Pd-catalyzed carbonylation protocol is described for the coupling of a large panel of aryl, heteroaryl, benzyl, vinyl and allyl halides 2 with the unusual N-hydroxysuccinimidyl (NHS) formate 1 as a CO surrogate to afford the corresponding valuable NHS esters 3. High conversion to the coupling products was achieved with up to 98% yield by means of Pd(OAc)(2)/Xantphos catalyst system.

  DOI：

  10.1021/acs.joc.5b01119
• 作为产物：
  描述：

  N-羟基丁二酰亚胺 、 甲酸 在 乙酸酐 作用下， 反应 18.0h， 以98%的产率得到2,5-dioxopyrrolidin-1-yl formate
  参考文献：
  名称：

  钯催化芳烃 C-H 噻蒽化合成酯

  摘要：

  已经开发出从容易获得的芳烃中高效钯催化合成酯的方法。这些 C-H 键酯化是通过区域选择性噻蒽化反应生成芳基-TT 盐实现的，芳基-TT 盐被视为反应性亲电底物，与苯酚甲酸酯和 N-羟基琥珀酰亚胺 (NHS) 甲酸酯偶联，从而获得苯酚酯和 NHS酯，分别在没有一氧化碳的情况下。在这种氧化还原中性钯催化条件下，可以高效制备多种功能性酯。合成应用的后期功能化和研究证明了已建立平台和这些产品的潜在应用。

  DOI：

  10.1021/acs.orglett.2c02330

文献信息

• Active Ester Functionalized Azobenzenes as Versatile Building Blocks
  作者：Sven Schultzke、Melanie Walther、Anne Staubitz

  DOI：10.3390/molecules26133916

  日期：——

  conditions for the introduction of NHS esters to azobenzenes and diazocines has been established. Yields were consistently high with very few exceptions. The NHS functionalized azobenzenes react with primary amines quantitatively. These amines are ubiquitous in biological systems and in material science.

  偶氮苯是重要的分子开关，但仍然难以选择性地官能化。已经建立了一种在温和条件下将 NHS 酯引入偶氮苯和重氮辛的高产率 Pd 催化交叉偶联方法。除了极少数例外，产量一直很高。NHS 官能化偶氮苯与伯胺定量反应。这些胺在生物系统和材料科学中无处不在。
• Synthesis of potential inhibitors of hemagglutination by influenza virus: chemoenzymic preparation of N-5 analogs of N-acetylneuraminic acid.
  作者：Michelle A. Sparks、Kevin W. Williams、Christine Lukacs、Andreas Schrell、Gregory Priebe、Andreas Spaltenstein、George M. Whitesides

  DOI：10.1016/s0040-4020(01)80502-0

  日期：1993.1

  A chemoenzymic route to neuraminic acid 2 is described. This method is based on conversion of N-carbobenzoxymannosamine (ManCBz) 3 to N-carbobenzoxyneuraminic acid (Neu5CBz) 4, catalyzed by Neu5Ac aldolase. The Neu5CBz 4 was converted to the α-methyl glycoside 8 and deprotected to afford the free amine 2. This procedure has been scaled up to generate 10-gram quantities of 2. N-Acylation of 2 produced

  描述了向神经氨酸2的化学酶途径。该方法基于由Neu5Ac醛缩酶催化的N-碳代苯甲氧基甘露糖胺（ManCBz）3到N-碳代苯并神经氨酸（Neu5CBz）4的转化。Neu5CBz 4转化为α-甲基糖苷8并脱保护得到游离胺2。此过程已按比例放大以生成10克数量的2。的N-酰化2产生几个新的N-酰基神经氨酸类似物; 在血凝抑制试验（HAI）中，已将它们评估为流感病毒与鸡红细胞粘附的抑制剂。神经氨酸2的这种制备 与其他文献程序进行比较。
• Fungal efflux pump inhibitors
  申请人：——

  公开号：US20030220338A1

  公开（公告）日：2003-11-27

  This invention relates to compounds that are efflux pump inhibitors and therefore are useful as potentiators of anti-fungal agents for the treatment of infections caused by fungi that employ an efflux pump resistance mechanism.

  本发明涉及一种能够抑制外排泵并且因此可用作抗真菌药物增效剂的化合物，用于治疗由采用外排泵耐药机制的真菌引起的感染。
• Jelokhani-Niaraki, Masood; Yoshioka, Katsumi; Takahashi, Hiroki, Journal of the Chemical Society. Perkin transactions II, 1992, # 7, p. 1187 - 1193
  作者：Jelokhani-Niaraki, Masood、Yoshioka, Katsumi、Takahashi, Hiroki、Kato, Fumio、Kondo, Michio

  DOI：——

  日期：——
• Palladium-Catalyzed Carbonylation of (Hetero)Aryl, Alkenyl and Allyl Halides by Means of <i>N-</i>Hydroxysuccinimidyl Formate as CO Surrogate
  作者：Anaïs Barré、Mihaela-Liliana Ţînţaş、Florent Alix、Vincent Gembus、Cyril Papamicaël、Vincent Levacher

  DOI：10.1021/acs.joc.5b01119

  日期：2015.7.2

  An efficient Pd-catalyzed carbonylation protocol is described for the coupling of a large panel of aryl, heteroaryl, benzyl, vinyl and allyl halides 2 with the unusual N-hydroxysuccinimidyl (NHS) formate 1 as a CO surrogate to afford the corresponding valuable NHS esters 3. High conversion to the coupling products was achieved with up to 98% yield by means of Pd(OAc)(2)/Xantphos catalyst system.