3-ethylidene-1-(4-methylphenyl)isoquinolin-4-one

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 异喹啉及其衍生物
• 英文名称: 3-ethylidene-1-(4-methylphenyl)isoquinolin-4-one
• 化学式: C₁₈H₁₅NO
• 分子量: 261.323
• InChiKey: UEWUOLKJFCQJGR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.2
• 重原子数：
  20
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.11
• 拓扑面积：
  29.4
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  4-(4-methylphenyl)-2,3-benzoxazin-1-one 、 烯丙基三苯基溴化膦 在 sodium hydride 作用下， 以 丁酮 为溶剂， 反应 26.0h， 以62%的产率得到3-ethylidene-1-(4-methylphenyl)isoquinolin-4-one
  参考文献：
  名称：

  Study of Insertion Reactions with Phosphorus Ylides − On Reactions between 4-(4-Methylphenyl)-2,3-benzoxazin-1-one and Alkylidene Phosphoranes

  摘要：

  4-(4-Methylphenyl)-2,3-benzoxazin-1-one (1) reacts thermally with a series of alkylidene phosphoranes and the relevant salts to give mainly substituted isoquinolines. Thus, compound 1 reacts with ester ylides 2a and 2b to give isoquinolones 7a and 7b, whereas with benzoylmethylenetriphenylphosphorane (3a), compound 7c was obtained together with the corresponding ylide 9a. The latter compound was treated with K2CO3 and then with polyphosphoric acid to give the isoquinolone 7c, With acetyl ylide 3b, o-diacetyl-alpha-naphthol 13 and cycloheptenone 14 were also obtained, in addition to 7d. On the other hand, isoquinolone derivatives 18, 21a, and 21b were successfully prepared by treatment of 1 with moderately (4a) and more reactive (4b, 4c) phosphonium salts.

  DOI：

  10.1002/1099-0690(200205)2002:10<1696::aid-ejoc1696>3.0.co;2-a

文献信息

• Study of Insertion Reactions with Phosphorus Ylides − On Reactions between 4-(4-Methylphenyl)-2,3-benzoxazin-1-one and Alkylidene Phosphoranes
  作者：Wafaa Mahmoud Abdou、Amin Farouk Mohammed Fahmy、Azza Abdel-Azeem Kamel

  DOI：10.1002/1099-0690(200205)2002:10<1696::aid-ejoc1696>3.0.co;2-a

  日期：2002.5

  4-(4-Methylphenyl)-2,3-benzoxazin-1-one (1) reacts thermally with a series of alkylidene phosphoranes and the relevant salts to give mainly substituted isoquinolines. Thus, compound 1 reacts with ester ylides 2a and 2b to give isoquinolones 7a and 7b, whereas with benzoylmethylenetriphenylphosphorane (3a), compound 7c was obtained together with the corresponding ylide 9a. The latter compound was treated with K2CO3 and then with polyphosphoric acid to give the isoquinolone 7c, With acetyl ylide 3b, o-diacetyl-alpha-naphthol 13 and cycloheptenone 14 were also obtained, in addition to 7d. On the other hand, isoquinolone derivatives 18, 21a, and 21b were successfully prepared by treatment of 1 with moderately (4a) and more reactive (4b, 4c) phosphonium salts.