5-[(E)-2-(4-Chloro-phenyl)-vinyl]-3-methyl-isoxazol-4-ylamine | 754985-41-6

• 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: 5-[(E)-2-(4-Chloro-phenyl)-vinyl]-3-methyl-isoxazol-4-ylamine
• 英文别名: 5-(4-Chlorostyryl)-3-methylisoxazol-4-amine；5-[(E)-2-(4-chlorophenyl)ethenyl]-3-methyl-1,2-oxazol-4-amine
• CAS: 754985-41-6
• 化学式: C₁₂H₁₁ClN₂O
• 分子量: 234.685
• InChiKey: GVKNAPAXGKQWTC-QPJJXVBHSA-N

物化性质

• 沸点：
  407.7±33.0 °C(Predicted)
• 密度：
  1.309±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  16
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.08
• 拓扑面积：
  52
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  5-[(E)-2-(4-Chloro-phenyl)-vinyl]-3-methyl-isoxazol-4-ylamine 在 ammonium cerium (IV) nitrate 、 氧气 作用下， 以 乙醇 、 二氯甲烷 为溶剂， 反应 2.5h， 生成 (E)-2-(5-(4-chlorostyryl)-3-methylisoxazol-4-yl)-2,3-dihydrospiro[benzo[f]isoindole-1,3'-indoline]-2',4,9-trione
  参考文献：
  名称：

  A facile synthesis, anti-inflammatory and analgesic activity of isoxazolyl-2,3-dihydrospiro[benzo[f]isoindole-1,3′-indoline]-2′,4,9-triones

  摘要：

  A new series of isoxazolyl-2,3-dihydrospiro[benzo[f]isoindole-1,3'-indoline]-2',4,9-triones (14) were synthesized by reaction of 4-amino-3-methyl-5-styrylisoxazole 10 with chloroacetic acid followed by a three component reaction with substituted isatins 12 and 1,4-naphthoquinone 13 using Ceric ammonium nitrate (CAN) catalyst under aerial oxidation condition. Structures of these compounds were established on the basis of IR, H-1 NMR, C-13 NMR and mass spectral data. The title compounds 14a-j were evaluated for their anti-inflammatory and analgesic activity. Compounds 14d, 14e and 14f exhibited potent anti-inflammatory and analgesic activity as that of standard drugs. (c) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2013.04.053
• 作为产物：
  描述：

  (E)-5-(4-chlorostyryl)-3-methyl-4-nitroisoxazole 在 盐酸 、 tin(ll) chloride 作用下， 以 四氢呋喃 为溶剂， 反应 2.0h， 生成 5-[(E)-2-(4-Chloro-phenyl)-vinyl]-3-methyl-isoxazol-4-ylamine
  参考文献：
  名称：

  Epoxidation of 3-methyl-4-N-acetyl-5-styrylisoxazoles

  摘要：

  An efficient synthesis of novel isoxazoloepoxides is described. The title compounds were obtained in high yields and without the use of chromatography. (c) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2007.05.012

文献信息

• Design, synthesis, antimicrobial, anti-inflammatory and analgesic activity of novel isoxazolyl pyrimido[4,5-b]quinolines and isoxazolyl chromeno[2,3-d]pyrimidin-4-ones
  作者：E. Rajanarendar、M. Nagi Reddy、S. Rama Krishna、K. Rama Murthy、Y.N. Reddy、M.V. Rajam

  DOI：10.1016/j.ejmech.2012.07.029

  日期：2012.9

  Novel series of 2-methyl-3-3-methyl-5-[(E)-2-phenyl-1-ethenyl]-4-isoxazolyl}-3,4-dihydropyrimido[4,5-b]quinolin-4-ones 5 and 3-3-methyl-5-[(E)-2-phenyl-1-ethenyl]-4-isoxazolyl}-3,4-dihydro-2H-chromeno[2,3-d]pyrimidin-4-ones 7 have been synthesized from isoxazolyl cyanoacetamide synthon 2. Compound 2 was obtained by reaction of 4-amino-3-methyl-5-styrylisoxazole 1 with ethyl cyanoacetate. Isoxazolyl

  2-甲基-3- 3-甲基-5-[（E）-2-苯基-1-乙烯基] -4-异恶唑基} -3,4-二氢嘧啶[4,5 - b ]喹啉-4的新系列-酮5和3- 3-甲基-5 - [（ë）-2-苯基-1-乙烯基] -4-异恶唑基} -3,4-二氢-2- ħ -chromeno [2,3- d ]嘧啶从异恶唑基氰基乙酰胺合成子2合成了-4-ones 7。通过使4-氨基-3-甲基-5-苯乙烯基恶唑1与氰基乙酸乙酯反应获得化合物2。异恶唑基嘧啶并[4,5 - b ]喹啉-4-酮5是从化合物2经与o的缩合得到的。-硝基硝基苯甲醛，然后用SnCl 2处理，随后进行串联N-乙酰化，然后用乙酸酐进行环脱水。通过与水杨醛反应并随后与甲醛环化，将化合物2转化为异恶唑基铬诺[2,3 - d ]嘧啶-4-酮7。化合物2 – 7的特征在于IR，1 H NMR，13 C NMR和质谱数据。对标题化合物5a – f和7a –
• Polyethylene glycol (PEG-400) promoted as an efficient and recyclable reaction medium for the one-pot eco-friendly synthesis of functionalized isoxazole substituted spirooxindole derivatives
  作者：Nagi Reddy Modugu、Praveen Kumar Pittala

  DOI：10.1039/c7nj03515b

  日期：——

  An efficient, inexpensive and environmentally friendly synthesis of novel isoxazole substituted spirooxindole-pyridopyrimidine/indenopyridine/chromenopyridine/naphthyridine/quinoline derivatives has been developed via one-pot three-component reaction of isoxazolyl enamino esters, isatins and 1,3-dimethylbarbituric acid/1,3-indandione/chromene-2,4-dione/quinoline-2,4-dione/naphthalene-1,2,4-trione/dimedone

  新颖异恶唑的一种高效，廉价且环境友好的合成取代spirooxindole-吡啶并嘧啶/ indenopyridine / chromenopyridine /萘/喹啉衍生物已被开发经由异恶唑基烯氨基酯，靛红与1,3-二甲基巴比妥酸/ 1,3-茚满二酮/色烯-2,4-二酮/喹啉-2,4-二酮/萘-1,2,4的一锅三组分反应-使用PEG-400作为溶剂和催化剂的三酮/二甲酮。选择了26种异恶唑基烯氨基酯，7种1,3-二酮化合物和11种取代的isatins进行文库验证。该方法的优点是其环境安全性，无催化剂性，操作简便，无金属操作，多种底物范围，高收率，优异的官能团耐受性和较短的反应时间，PEG-400可以回收和再利用。
• p-TSA-catalyzed facile and efficient one-pot eco-friendly synthesis of novel isoxazolyl amino furo[3,2-c]quinolinone derivatives in aqueous medium
  作者：Nagi Reddy Modugu、Praveen Kumar Pittala

  DOI：10.1016/j.tetlet.2017.08.062

  日期：2017.10

  operationally simple approach for the synthesis of novel isoxazolyl amino furo[3,2-c]quinolinone derivatives by a one-pot three-component reaction of 4-amino-3-methyl-5 styrylisoxazoles, aryl glyoxal monohydrates and 4-hydroxy-1-methyl-2-quinolinone using p-TSA as the catalyst in aqueous medium was developed. The protocol proves to be an efficient and an environmentally benign in terms of high yields, operational

  通过4-氨基-3-甲基-5苯乙烯基恶唑，芳基乙二醛一水合物和4-水的一锅三组分反应合成新型异恶唑基氨基呋喃[3,2- c ]喹啉酮衍生物的绿色且操作简单的方法以p -TSA为催化剂，在水性介质中开发了羟基-1-甲基-2-喹啉酮。从高产率，操作简便，反应简捷，与各种底物的相容性，水作为溶剂和易于纯化等方面来看，该协议被证明是一种有效且对环境无害的方法。
• Water-acetic acid mediated an efficient and eco-friendly protocol for the one-pot synthesis of bis-isoxazolyl amino dihydro-1 H -indol-4(5 H )-ones under mild reaction conditions
  作者：Modugu Nagi Reddy、Pittala Praveen Kumar

  DOI：10.1016/j.tetlet.2017.11.027

  日期：2017.12

  A cost-effective and eco-friendly straightforward synthesis of new bis-isoxazolyl amino dihydro-1H-indol-4(5H)-ones is successfully achieved via one-pot three-component reaction of N-isoxazolyl enaminone, aryl glyoxal monohydrates and 4-amino-3-methyl-5-styrylisoxazoles by using water as a reaction medium and acetic acid (AcOH) as cheap and green promoter. The protocol proves to be an efficient and

  通过N-异恶唑基烯胺酮，芳基乙二醛一水合物的一锅三组分反应成功地实现了经济高效且环保的新型双-异恶唑基氨基二氢-1 H-吲哚-4（5 H）-酮的合成和4-氨基-3-甲基-5-苯乙烯基恶唑，以水为反应介质，以乙酸（AcOH）为廉价绿色助催化剂。从高产率，低反应时间，操作简便，无金属和广泛的基材范围来看，该协议被证明是一种有效且对环境无害的方法。最重要的是，此反应过程是绿色的。
• Acetic acid promoted an efficient and eco-friendly one-pot synthesis of functionalized novel isoxazolyl amino chromenopyrrole derivatives in aqueous medium
  作者：Nallamothu Vanaja Rani、Ravindhranath Kunta

  DOI：10.1080/00397911.2020.1846058

  日期：2021.2.16

  An efficient, economical, and environmentally friendly method has been reported for one-pot synthesis of isoxazolyl amino chromenopyrrole derivatives from 4-amino-3-methyl-5-styrylisoxazoles, aryl ...

  已经报道了一种高效、经济且环保的方法，用于从 4-氨基-3-甲基-5-苯乙烯基异恶唑、芳基...