3-(4'-chlorobenzoylamino)-5-methylisoxazole | 88812-93-5

• 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: 3-(4'-chlorobenzoylamino)-5-methylisoxazole
• 英文别名: 4-chloro-N-(5-methyl-1,2-oxazol-3-yl)benzamide
• CAS: 88812-93-5
• 化学式: C₁₁H₉ClN₂O₂
• mdl: MFCD01200387
• 分子量: 236.658
• InChiKey: CVDHQYKCNQTJJO-UHFFFAOYSA-N

物化性质

• 熔点：
  215-216 °C(Solv: toluene (108-88-3))
• 沸点：
  310.7±37.0 °C(Predicted)
• 密度：
  1.371±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  16
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.09
• 拓扑面积：
  55.1
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  3-(4'-chlorobenzoylamino)-5-methylisoxazole 在 sodium azide 、 五氯化磷 、 sodium acetate 作用下， 以 水 、 丙酮 为溶剂， 反应 12.5h， 生成 5-(4-Chloro-phenyl)-1-(5-methyl-isoxazol-3-yl)-1H-tetrazole
  参考文献：
  名称：

  Synthesis of 1-(5-Methylisoxazole-3-yl)-5-Aryl-Tetrazoles and its Pyrolysis

  摘要：

  3-Aroylamino-5-methylisoxazoles (2) were obtained by the reaction of 3-amino-5-methylisoxazole (1) with different aroyl chlorides. These amides on reaction with phosphorous pentachloride followed by sodium azide yielded 1-(5-methylisoxazole-3-yl)-5-aryltetrazo (4). Pyrolysis of the tetrazoles thus obtained resulted in the formation of 3-aryl-6-acetyl(1,2-4)triazines (9).

  DOI：

  10.1080/00397919908086453
• 作为产物：
  描述：

  3-p-chlorobenzalamino-5-methylisoxazole 在 间氯过氧苯甲酸 作用下， 反应 1.5h， 生成 3-(4'-chlorobenzoylamino)-5-methylisoxazole
  参考文献：
  名称：

  Chary, T. Jagan Mohana; Krishnamurthy, A., Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 1995, vol. 34, # 1, p. 65 - 66

  摘要：

  DOI：

文献信息

• Experimental and DFT Studies on Competitive Heterocyclic Rearrangements. 3. A Cascade Isoxazole−1,2,4-Oxadiazole−Oxazole Rearrangement
  作者：Andrea Pace、Paola Pierro、Silvestre Buscemi、Nicolò Vivona、Giampaolo Barone

  DOI：10.1021/jo802081k

  日期：2009.1.2

  The thermal rearrangements of 3-acylamino-5-methylisoxazoles 1 have been investigated under basic and neutral conditions and interpreted with the support of computational data. The density functional theory (DFT) study on the competitive routes available for the base-catalyzed thermal rearrangement of isoxazoles 1 showed that the Boulton−Katritzky (BK) rearrangement, producing the less stable 3-acetonyl-1

  已经在碱性和中性条件下研究了3-酰基氨基-5-甲基异恶唑1的热重排，并在计算数据的支持下进行了解释。密度泛函理论（DFT）对可用于异恶唑1的碱催化热重排的竞争途径的研究表明，Boulton-Katritzky（BK）重排产生不稳定的3-丙酮基-1,2,4-恶二唑5与迁移亲核攻击环化（MNAC）或环收缩环扩展（RCRE）相比，它是一个更受青睐的过程。反过来，反应温度的升高将促进恶二唑5的MNAC ，从而产生更稳定的2-酰基氨基恶唑8。因此，可以以级联BK-MNAC重排为例，将3-酰基氨基异恶唑1热重排为恶唑8，该级联BK-MNAC重排为3-丙酮基1,2,4-恶二唑5作为辅助中间体。
• Prameela, B.; Rajanarendar, E.; Rao, C. Janakirama, Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 1986, vol. 25, p. 1209 - 1213
  作者：Prameela, B.、Rajanarendar, E.、Rao, C. Janakirama、Murthy, A. Krishna

  DOI：——

  日期：——
• PRAMEELA, B.;RAJANARENDAR, E.;RAO, C. JANAKIRAMA;MURTHY, A. KRISHNA, INDIAN J. CHEM., 25,(1986) N 12, 1209-1213
  作者：PRAMEELA, B.、RAJANARENDAR, E.、RAO, C. JANAKIRAMA、MURTHY, A. KRISHNA

  DOI：——

  日期：——
• Synthesis of 1-(5-Methylisoxazole-3-yl)-5-Aryl-Tetrazoles and its Pyrolysis
  作者：Kamala K. Vasu、K. Kondal Reddy

  DOI：10.1080/00397919908086453

  日期：1999.8

  3-Aroylamino-5-methylisoxazoles (2) were obtained by the reaction of 3-amino-5-methylisoxazole (1) with different aroyl chlorides. These amides on reaction with phosphorous pentachloride followed by sodium azide yielded 1-(5-methylisoxazole-3-yl)-5-aryltetrazo (4). Pyrolysis of the tetrazoles thus obtained resulted in the formation of 3-aryl-6-acetyl(1,2-4)triazines (9).
• Chary, T. Jagan Mohana; Krishnamurthy, A., Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 1995, vol. 34, # 1, p. 65 - 66
  作者：Chary, T. Jagan Mohana、Krishnamurthy, A.

  DOI：——

  日期：——