N-phenylhydrazono α-bromoglyoxylate d'ethyle | 35257-03-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: N-phenylhydrazono α-bromoglyoxylate d'ethyle
• 英文别名: C-ethoxycarbonyl-N-phenylhydrazonoyl bromide；bromo-phenylhydrazono-acetic acid ethyl ester；Phenylhydrazono-bromessisaeure-aethylester；Oxalsaeure-aethylester-(bromid-phenylhydrazon)；Brom-phenylhydrazono-essigsaeure-aethylester；Ethyl 2-bromo-2-(phenylhydrazinylidene)acetate
• CAS: 35257-03-5
• 化学式: C₁₀H₁₁BrN₂O₂
• 分子量: 271.114
• InChiKey: ZGHYJLGEHMXZIP-UHFFFAOYSA-N

物化性质

• 熔点：
  82-83 °C
• 沸点：
  323.8±25.0 °C(Predicted)
• 密度：
  1.42±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.2
• 重原子数：
  15
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  50.7
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  N-phenylhydrazono α-bromoglyoxylate d'ethyle 在 水 、 三乙胺 、 potassium hydroxide 作用下， 以 甲醇 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 18.0h， 生成 2-(2-oxo-3-(phenylamino)indolin-3-yl)acetonitrile
  参考文献：
  名称：

  Synthesis of Oxindolyl Pyrazolines and 3-Amino Oxindole Building Blocks via a Nitrile Imine [3 + 2] Cycloaddition Strategy

  摘要：

  The [3 + 2] dipolar cycloaddition reaction of nitrite imines with 3-alkylidene oxindoles is described. The pyrazoline spiroadducts were obtained in high yields and with excellent regio- and diastereoselectivities. These spirocyclic intermediates have been elaborated to synthetically versatile 3-amino oxindole building blocks such as beta-amino nitrile, 1,3-diamine, and pyrrolo[2,3-b]indoline derivatives.

  DOI：

  10.1021/ol302425h
• 作为产物：
  描述：

  3-oxo-2-(phenylhydrazono)butyric acid ethyl ester 在 溴 、 sodium acetate 、 溶剂黄146 作用下， 生成 N-phenylhydrazono α-bromoglyoxylate d'ethyle 、 bromo-(4-bromo-phenylhydrazono)-acetic acid ethyl ester
  参考文献：
  名称：

  Bowack; Lapworth, Journal of the Chemical Society, 1905, vol. 87, p. 1859

  摘要：

  DOI：

文献信息

• Synthesis of novel spiro-pyrazole and spiro-isoxazoline derivatives of 9α- and 9β-hydroxyparthenolide
  作者：Fatima Outahar、Mohamed Moumou、Abdellah Hannioui、El Mostapha Rakib、Lahcen El Ammari、Mohamed Saadi、Mohamed Akssira

  DOI：10.1016/j.tetlet.2020.152409

  日期：2020.10

  A series of novel spiropyrazoles and spiroisoxazolines was efficiently synthesized. Structural modifications were performed at the C-9 and C-13 positions of 9α- and 9β-hydroxyparthenolide, which were isolated from the aerial parts of Anvillea radiata. The structures and stereochemistry of the cycloadducts were fully established by spectroscopic methods including X-ray diffraction data.

  高效合成了一系列新型螺吡唑和螺异恶唑啉。结构修饰是在9α-和9β-羟基单酚的C-9和C-13位置进行的，这些位置是从辐射小ville的空中部分分离出来的。通过包括X射线衍射数据在内的光谱方法可以完全确定环加合物的结构和立体化学。
• Reaction of Hydrazonoyl Halides 51¹: A Facile Synthesis of 5-Arylthiazoles and Triazolino[4,3-<b> <i>a</i> </b>]pyrimidines as Antimicrobial Agents
  作者：Abdou O. Abdelhamid、Abdelwahed R. Sayed、Yasser H. Zaki

  DOI：10.1080/10426500701242145

  日期：2007.6.1

  were synthesized with good yields from reactions of hydrazonoyl halides with 5-substituted-3-phenyl-4,5-dihydropyrazole-1-carboximidothionic acid, pyrimidine-2-thione, methyl carbodithioate, respectively. All structures of the newly synthesized compounds were elucidated by elemental analysis, spectral data, and alternative synthesis methods. Newly developed compounds are capable of inhibiting the growth

  [5-取代的 2-(3-苯基-5-取代的 2-吡唑啉基)(1,3-噻唑-4-基)]苯基二氮烯、三唑并[3,4-a]嘧啶和 2,3-二氢-1 ,3,4-噻二唑分别由腙酰卤与 5-取代-3-苯基-4,5-二氢吡唑-1-羧基亚胺硫酮酸、嘧啶-2-硫酮、碳二硫酸甲酯反应合成，收率良好。通过元素分析、光谱数据和替代合成方法阐明了新合成化合物的所有结构。新开发的化合物能够极大地抑制细菌（革兰氏阳性和革兰氏阴性）的生长。
• New routes to steroidal heterocyclic derivatives: Synthesis of biologically active pyrazolyl- and isoxazolylpregnene derivatives
  作者：Abdou O. Abdelhamid、Mervat M. Abdelhalim、Gamal A. Elmegeed

  DOI：10.1002/jhet.5570440102

  日期：2007.1

  Pyrazolyl- and isoxazolylpregnene derivatives were synthesized from the appropriate hydrazonoyl chlorides and hydroximoyl chlorides with enaminoprogesterone derivative. The newly synthesized compounds were elucidated by elemental analysis, spectral data and chemical transformation. Some products were tested towards some bacteria and some Fungal-plant pathogens

  吡唑基和异恶唑基戊二烯衍生物是由适当的酰氯和羟肟基氯与烯胺基孕酮衍生物合成的。通过元素分析，光谱数据和化学转化来阐明新合成的化合物。对某些产品进行了针对某些细菌和某些真菌植物病原体的测试
• Facile Synthesis of Thiophene- and 1,3,4-Thiadiazole-Based Heterocycles
  作者：Kamal M. Dawood、Eman A. Ragab、Ahmad M. Farag

  DOI：10.1080/10426500903299919

  日期：2010.7.30

  Treatment of 3-cyanoacetylpyrazole derivative 1 with phenyl isothiocyanate in potassium hydroxide at room temperature followed by α-haloketones 4a–d and hydrazonoyl halides 10a–e gave the corresponding pyrazolylthiophene 6a–d and pyrazolyl-1,3,4-thiadiazole 12a–e derivatives, respectively.

  在室温下在氢氧化钾中用异硫氰酸苯酯处理 3-氰基乙酰基吡唑衍生物 1，然后用 α-卤代酮 4a-d 和腙酰卤 10a-e 得到相应的吡唑基噻吩 6a-d 和吡唑基-1,3,4-噻二唑 12a-e衍生品，分别。
• Synthesis of bipyrazole and 1,3,4-thiadiazole derivatives
  作者：Kamal M. Dawood、Eman A. Ragab、Ahmad M. Farag

  DOI：10.3184/030823409x12528547964044

  日期：2009.10

  New hydrazonoyl bromides reacted with several C-nucleophiles to give the corresponding bipyrazoles. Treatment of 3-cyanoacetylpyrazole derivatives with phenyl isothiocyanate in potassium hydroxide followed by hydrazonoyl bromides gave the corresponding pyrazolyl-1,3,4-thiadiazoles.

  新的肼酰溴与几种 C-亲核物反应，得到相应的双吡唑。在氢氧化钾中用异硫氰酸苯酯处理 3-氰基乙酰基吡唑衍生物，然后用肼酰溴化物处理，可得到相应的吡唑-1,3,4-噻二唑。