(1E)-2-(2-呋喃基)-N-羟基-2-氧代亚氨代乙酰氯化物 | 23714-62-7

• 分子结构分类: 有机化合物 - 有机氧化合物
• 中文名称: (1E)-2-(2-呋喃基)-N-羟基-2-氧代亚氨代乙酰氯化物
• 英文名称: 2-(ω-chloro-ω-hydroxyiminoacetyl)furan
• 英文别名: 2-<α-Isonitroso-α-chlor-acetyl>-furan；2-furan-2-yl-N-hydroxy-2-oxo-acetimidoyl chloride；2-(furan-2-yl)-N-hydroxy-2-oxoethanimidoyl chloride
• CAS: 23714-62-7
• 化学式: C₆H₄ClNO₃
• 分子量: 173.556
• InChiKey: MZACRVOYDMVPGO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  11
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  62.8
• 氢给体数：
  1
• 氢受体数：
  4

安全信息

• 海关编码：
  2932190090

反应信息

• 作为反应物：
  描述：

  (1E)-2-(2-呋喃基)-N-羟基-2-氧代亚氨代乙酰氯化物 、 3-hydroxy-1-(5-methyl-1-phenyl-1H-1,2,3-triazole-4-yl)prop-2-en-1-one sodium salt 在 sodium carbonate 作用下， 以 neat (no solvent) 为溶剂， 反应 0.25h， 以96%的产率得到(3-(furan-2-carbonyl)isoxazol-4-yl)(5-methyl-1-phenyl-1H-1,2,3-triazol-4-yl)methanone
  参考文献：
  名称：

  含三唑部分的吡唑并[1,5-a]嘧啶，Azolo [3,4-d]哒嗪和硫代诺[2,3-b]吡啶的绿色一锅无溶剂合成

  摘要：

  吡唑并[1,5- a ]嘧啶，[1,2,4]三唑并[1,5- a ]嘧啶，8,10-二甲基-2-（5-甲基-1-苯基-4,5-二氢-1 H -1,2,3-三唑-4-基）吡啶基[2'，3'：3,4]-吡唑并[1,5- a ]嘧啶，苯并[4,5]咪唑[1， 2‐ a ]嘧啶通过杂环胺和3−羟基-1-（5-甲基-1-苯基-1 H -1,2,3-三唑-4基）丙-2-烯-1-酮钠被执行。另外，从钠3-羟基-1-（5-甲基-1-苯基-异恶唑1，和吡唑的合成ħ 1,2,3-三唑-4-基）丙-2-烯-1-酮和分别制备了羟酰氯和酰卤。类似地，（1,2,3-三唑-4-基）噻吩[2,3- b从获得]吡啶衍生物钠3-羟基-1-（5-甲基-1-苯基-1- ħ -1,2,3-三唑-4-基）丙-2-烯-1-酮和氰基硫代随后它与活性亚甲基化合物反应。除了对所有合成化合物进行全面表征外，还对它们进行了测试以评估其抗菌活性，

  DOI：

  10.1002/jhet.2343
• 作为产物：
  描述：

  2-(2-hydroxyimino-1-oxoethyl)furan 在 N-氯代丁二酰亚胺 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 1.0h， 生成 (1E)-2-(2-呋喃基)-N-羟基-2-氧代亚氨代乙酰氯化物
  参考文献：
  名称：

  羟基脒衍生物作为高效选择性吲哚胺-2,3-双加氧酶 1 抑制剂的发现

  摘要：

  在这项研究中，通过基于结构的药物设计，一系列新型羟基脒衍生物被鉴定为有效和选择性的 IDO1 抑制剂。其中，化合物13-15和18表现出良好的酶和细胞活性。化合物18在小鼠、大鼠和狗中显示出改善的生物利用度（分别为 F% = 44%、58.8%、102.1%）。化合物18具有合理的体内药代动力学特性，在转基因 MC38 异种移植小鼠模型中进行了进一步评估。化合物18与PD-1单克隆抗体的组合显示出协同抗肿瘤作用。这些数据表明化合物18作为一种潜在的癌症免疫治疗剂，应该值得进一步研究。

  DOI：

  10.1021/acsmedchemlett.0c00443

文献信息

• Convenient method for synthesis of various fused heterocycles via utility of 4-acetyl-5-methyl-1-phenyl-pyrazole as precursor
  作者：Sobhi MOHAMED GOMHA、Ahmad SAMI SHAWALI、Abdou OSMAN ABDELHAMID

  DOI：10.3906/kim-1311-12

  日期：——

  A new, less expensive, solvent-free procedure was developed for the synthesis of some new derivatives of various fused heterocyclic ring systems, namely azolopyridazine, azolotriazine, azinotriazine, thienopyridine, and pyrazolopyridine. The structures of the products prepared were established by their spectral data and elemental analyses. Eight compounds were evaluated for their in vitro antimicrobial activity. Some of the tested compounds exhibited moderate to significant antibacterial and antifungal activities.

  开发了一种新的、更经济的无溶剂方法，用于合成各种融合杂环系统的若干新型衍生物，包括吖啶并嘧嗪、吖啶并三嗪、氰基三嗪、噻吩并吡啶和吡唑并吡啶。通过其光谱数据和元素分析确定了制备产物的结构。对八种化合物进行了体外抗菌活性评估，其中一些测试化合物显示出中等到显著的抗细菌和抗真菌活性。
• Reactions With Hydrazonoyl Halides 45: Synthesis of Some New Triazolino[4,3‐<i>a</i>]pyrimidines, Pyrazolo[3,4‐<i>d</i>]pyridazines, Isoxazolo[3,4‐<i>d</i>]pyridazines, and Thieno[2,3‐<i>b</i>]pyridines
  作者：Abdou O. Abdelhamid、Ali A. Al‐Atoom

  DOI：10.1080/00397910500330593

  日期：2006.2

  Abstract Triazolino[4,3‐a]pyrimidines pyrazolo[3,4‐d]pyridazines and isoxazolo[3,4‐d]pyridazines were synthesized from hydrazonoyl halides. Also, 3‐aminothieno[2,3‐b]pyridines and pyrimidino[4′,5′:4,5]thieno[2,3‐b]pyridines were synthesized from cynothioacetamide. Structures of the newly synthesized compounds were established on the basis of elemental analyses and spectral data.

  摘要 三唑并[4,3-a]嘧啶类吡唑并[3,4-d]哒嗪和异恶唑并[3,4-d]哒嗪由腙酰卤化物合成。此外，3-氨基噻吩并[2,3-b]吡啶和嘧啶并[4',5':4,5]噻吩并[2,3-b]吡啶由犬硫代乙酰胺合成。新合成化合物的结构是在元素分析和光谱数据的基础上建立的。
• Useful Precursors for Synthesis of Some New Azolo[3,4-<i>d</i>]pyridiazines, Azolo[1,5-<i>a</i>]pyrimidines, Azolo[5,1-<i>c</i>]triazines, Pyrazoles, and Benzo[b][l,4]diazepine
  作者：Abdou O. Abdelhamid、Abdelgawad A. Fahmi、Basma S. Baaiu

  DOI：10.1002/jhet.2507

  日期：2016.11

  Pyrazolo[3,4‐d]pyridazines, isoxazolo[3,4‐d]pyridazines, azolo[1,5‐a]pyrimidines, azolo[5,1‐c]triazines, pyrazoles, and benzo[b][l,4]diazepine were synthesized from the appropriate hydrazonoyl halides, hydroximoyl halides, heterocyclic amines, diazotized heterocyclic amines, arenediazonium chlorides, and o‐phenylenediamines with appropriate of sodium 3‐(5‐bromobenzofuran‐2‐yl)‐3‐oxoprop‐1‐en‐1‐olate

  吡唑并[3,4- d ]哒嗪，异恶唑并[3,4- d ]哒嗪类，三唑并[1,5-一个]嘧啶，三唑并[5,1- c ^ ]三嗪，吡唑，和苯并[ b ] [1,4] 4]二氮杂from是由适当的酰卤，羟甲酰卤，杂环胺，重氮化杂环胺，槟榔二氯化铵和邻苯二胺与适当的3-（5-溴苯并呋喃-2-基）-3-氧代丙-1-酸钠合成的烯-1-醇或1-（5-溴苯并呋喃-2-基）-3-（二甲氨基）丙-2-烯-1-酮。尽可能通过元素分析，光谱数据和替代合成来阐明新合成的化合物。
• Design and Synthesis of Some New Pyrazolo[1,5-<i>a</i>]pyrimidines, Pyrazolo[5,1-<i>c</i>]triazines, Pyrazolo[3,4-<i>d</i>]pyridazines, and Isoxazolo[3,4-<i>d</i>]pyridazines Containing the Pyrazole Moiety
  作者：Abdou O. Abdelhamid、Abdelgawad A. Fahmi、Karema N. M. Halim

  DOI：10.1080/00397911.2011.616639

  日期：2013.4.18

  Abstract GRAPHICAL ABSTRACT

  摘要图形抽象
• Synthesis and Biological Evaluation of Some New Pyridines, Isoxazoles and Isoxazolopyridazines Bearing 1,2,3-Triazole Moiety
  作者：anhar hassan、Huda Rashdan、sara nabil、dina elnagar

  DOI：10.32383/appdr/103101

  日期：2019.6.28

  Some new isoxazole derivatives 3a-d were synthesized via the reaction of 3-(dimethylamino)-1-(5-methyl-1-(3-nitrophenyl)-1H-1,2,3-triazol-4-yl)prop-2-en-1-one (1) with different hydroximoyl chlorides derivatives 2a-d. From these new isoxazoles 3a-d a new series of isoxazolopyridazines 4a-d was derived using hydrazine hydrate. In addition, enaminone 1 was reacted with ethyl acetoacetate to afford the corresponding ester derivative 6, the latter was submitted to react with different chemical reagents to obtain a variety of bioactive substituted pyridine derivatives. The azido derivative 14, was used as the key molecule for the synthesis of new urea and aryl carbamate derivatives upon its reaction with different amines and phenol through Curtius rearrangement. The chemical compositions of all the new compounds were investigated from their spectral and microanalytical data. The synthesized compounds were tested for their pharmacological potency as, anti-hepatic cancer and anti-microbial agents. Most of the tested compounds showed good anti-hepatic cancer results comparing with the standard drug doxorubicin especially when their toxic effects on the normal cell lines were studied. Referring to the anti-microbial test most of the compounds showed strong effects.