(1-cyclohexyl-3-phenyl-aziridin-2-yl)-p-tolyl-methanone | 52599-14-1

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (1-cyclohexyl-3-phenyl-aziridin-2-yl)-p-tolyl-methanone
• 英文别名: 3-(p-Methyl-benzoyl)-1-cyclohexyl-2-phenyl-aziridin；Methanone, (1-cyclohexyl-3-phenyl-2-aziridinyl)(4-methylphenyl)-, trans-；(1-cyclohexyl-3-phenylaziridin-2-yl)-(4-methylphenyl)methanone
• CAS: 52599-14-1
• 化学式: C₂₂H₂₅NO
• 分子量: 319.447
• InChiKey: ABWDYIPGRJQNNT-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.2
• 重原子数：
  24
• 可旋转键数：
  4
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.41
• 拓扑面积：
  20.1
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (1-cyclohexyl-3-phenyl-aziridin-2-yl)-p-tolyl-methanone 在 4-亚硝基间甲酚 作用下， 以 苯 为溶剂， 反应 24.0h， 生成 3,5-dicyclohexyl-2-phenyl-4,6-di-p-tolyl-3,5-dihydro-2H-pyrrolo[3,4-d]oxazole
  参考文献：
  名称：

  对亚硝基苯酚与2-芳酰基氮丙啶的反应一步合成3,5-二氢-2 H-吡咯并[3,4- d ]恶唑

  摘要：

  在2-或3-位带有电子释放取代基的1-烷基-2-芳酰基-3-芳基氮丙啶与取代的对亚硝基苯酚反应，生成3,5-二氢-2 H-吡咯并[3,4- d ]恶唑。硝酮，芳基和芳酰基亚胺作为次要产物的分离支持以两个连续的1,3-偶极加成来解释反应，其中第二个区域特异性加成是自催化的，随后是Paal-Knorr缩合反应。

  DOI：

  10.1039/p19720001459

文献信息

• Reaction of 3-aroylaziridines with diphenylcyclopropenone. Synthesis and properties of novel 4-aroyl-4-oxazolines
  作者：J. W. Lown、R. K. Smalley、G. Dallas、T. W. Maloney

  DOI：10.1139/v70-014

  日期：1970.1.1

  3-Aroylaziridines and 3-acylaziridines react with diphenylcyclopropenone with the formation of novel 4-aroyl-4-oxazolines and 4-acyl-4-oxazolines respectively. The unusual physical and chemical properties of these reactive heterocycles are discussed.

  3-Aroylaziridines 和 3-acylaziridines 与二苯基环丙烯酮反应，分别形成新的 4-aroyl-4-oxazolines 和 4-acyl-4-oxazolines。讨论了这些反应性杂环的不寻常的物理和化学性质。
• Reaction of 3-aroylaziridines with aryl isothiocyanates
  作者：J. W. Lown、G. Dallas、T. W. Maloney

  DOI：10.1139/v69-589

  日期：1969.10.1

  3-Aroylaziridines react with a variety of aryl isothiocyanates in refuxing benzene to give either (a) 4-aroyl-5-arylamino-4-thiazolines by a [2 + 3] cycloaddition and/or (b) 2-arylamino-4-aroyl-4-thiazolines. When the N-substituent of the aziridine is cyclohexyl or isopropyl the product type (a) is isolated in greater quantity, but when the N-substituent is methyl, product type (b) is isolated in greater quantity. The reactions provide convenient one-step syntheses of new 4-aroyl-4-thiazolines.

  3-芳酰基环氧丙烷与各种芳基异硫氰酸酯在回流苯中反应，可产生(a) [2+3]环加成反应得到4-芳酰基-5-芳基氨基-4-噻唑烷和/或(b) 2-芳基氨基-4-芳酰基-4-噻唑烷。当环氧丙烷的N-取代基为环己基或异丙基时，产物类型(a)的产量较大，但当N-取代基为甲基时，产物类型(b)的产量较大。这些反应提供了新型4-芳酰基-4-噻唑烷的便利一步合成方法。
• 1,3-Dipolar cycloaddition of nitrosonaphthols to 3-aroylazindines. Novel syntheses of substituted naphtho[1,2-<i>d</i>]oxazoles and naphtho[2,1-<i>d</i>]oxazoles
  作者：J. W. Lown、J. P. Moser

  DOI：10.1139/v70-371

  日期：1970.7.15

  A series of 3-aroyl-2-arylaziridines underwent 1,3-dipolar cycloadditions in both orientations to the nitrogen–oxygen bond of 1-nitroso-2-naphthol. Spontaneous 1,3-cleavage of the intermediate oxadiazolidines to nitrones and cyclodehydration of the latter afforded both 2-aryl- and 2-aroylnaphtho-[1,2-d]oxazoles in good yields. The interpretation of the reaction received confirmation by independent

  一系列 3-aroyl-2-arylaziridines 与 1-nitroso-2-naphthol 的氮氧键发生 1,3-偶极环加成反应。中间体恶二唑烷自发 1,3-裂解为硝酮，后者环化脱水以良好的产率得到 2-芳基-和 2-芳酰基萘-[1,2-d] 恶唑。反应的解释得到了几种 2-芳酰基萘并 [1,2-d] 恶唑的独立、明确合成的确认。
• Reaction of 3-aroylaziridines with diphenylcyclopropenone. 1,3-Dipole cascade from azomethine ylide to carbonyl ylide
  作者：Kiyoshi Matsumoto、Yukio Ikemi、Mitsuo Toda、Akikazu Kakehi、Takane Uchida、James William Lown

  DOI：10.1016/0040-4039(95)00436-g

  日期：1995.4

  The novel formation of anhydro-3-hydroxy-2,4-diphenyl-6-arylpyrylium hydroxide in the reaction of 3-aroylaziridines with diphenylcyclopropenones and their 1,3-dipolar cycloaddition reactions with diphenylcyclopropenone, N-phenylmaleimide, dimethyl fumarate, and dimethyl maleate were described.

  3-芳基氮丙啶与二苯基环丙烯酮的反应中新形成的脱水-3-羟基-2,4-二苯基-6-芳基吡啶鎓及其与二苯基环丙烯酮，N-苯基马来酰亚胺，富马酸二甲酯和二甲基的1,3-偶极环加成反应描述了马来酸盐。
• Matsumoto, Kiyoshi; Iida, Hirokazu; Uchida, Takane, Canadian Journal of Chemistry, 1994, vol. 72, # 10, p. 2108 - 2117
  作者：Matsumoto, Kiyoshi、Iida, Hirokazu、Uchida, Takane、Yabe, Yoshimi、Kakehi, Akikazu、Lown, J. William

  DOI：——

  日期：——