3-(p-tolyl)-1-oxo-2,3,4,5,6,7-hexahydro-1H-isoindole | 151830-93-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯啉
• 英文名称: 3-(p-tolyl)-1-oxo-2,3,4,5,6,7-hexahydro-1H-isoindole
• 英文别名: 1-p-tolyl-2,3,4,5,6,7-hexahydroisoindol-3-one；2,3,4,5,6,7-Hexahydro-3-(4-methylphenyl)-1H-isoindol-1-one；3-(4-methylphenyl)-2,3,4,5,6,7-hexahydroisoindol-1-one
• CAS: 151830-93-2
• 化学式: C₁₅H₁₇NO
• 分子量: 227.306
• InChiKey: YTBKXBMEVYUOPL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  17
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  29.1
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为产物：
  描述：

  2-p-toluoylcyclohexanecarboxylic acid 在 formamide 作用下， 反应 4.0h， 以41%的产率得到3-(p-tolyl)-1-oxo-2,3,4,5,6,7-hexahydro-1H-isoindole
  参考文献：
  名称：

  Synthesis and Structural Study of New Saturated Isoindol-1-one Derivatives

  摘要：

  Condensation of 2-p-toluoylcyclohexanecarboxylic acid (1a,b) with primary amines gave the corresponding hexahydroisoindol-1-ones (2a-g) in good yield. The octahydro derivatives (4a-g) were prepared from cis- and trans-hexahydro-1-(2H)-phthalazinone (3a,b) by reduction with zinc-hydrochloric acid via ring contraction. Stereoselective synthesis of cis-N-phenyloctahydroisoindol-1-one (4h) was performed starting from 2b by reduction with magnesium-methanol at room temperature. Configurational assignments of cis and trans isomers were based on H-1- and C-13-nmr spectroscopic studies.

  DOI：

  10.3987/com-93-6366

文献信息

• A retro Diels–Alder method for the preparation of pyrrolo[1,2-a]pyrimidinediones from diexo-aminooxanorbornenecarboxamide
  作者：Géza Stájer、Angela E. Szabó、Pál Sohár、Antal Csámpai、Reijo Sillanpää

  DOI：10.1016/j.molstruc.2005.09.011

  日期：2006.2

  with the oxocarboxylic acids: 4-oxopentanoic acid, p-chlorobenzoylpropionic acid or 2-formylbenzoic acid, the pyrrolo[1,2-a]pyrimidinediones 2 and 3 or pyrimido[1,2-a]isoindoledione 4 were formed on cyclization and thermolysis, when the parent cycles decomposed via the loss of furan to give 2–4 in a retro Diels–Alder reaction. With cis-or trans-2-aroylcyclohexanecarboxylic acids as starting compounds

  摘要 通过 diexo-3-amino-7-oxanorbornene-2-carboxamide 1 与氧代羧酸：4-氧代戊酸、对氯苯甲酰基丙酸或 2-甲酰基苯甲酸的反应，吡咯并[1,2-a]嘧啶二酮 2和 3 或嘧啶并[1,2-a]异吲哚二酮 4 在环化和热解过程中形成，当母体循环通过呋喃的损失分解，在逆狄尔斯-阿尔德反应中得到 2-4。以顺式或反式-2-芳酰基环己烷羧酸为起始化合物，形成了1-芳酰基六氢异吲哚-3-酮（5-8）；苯基取代的衍生物得到非对映体混合物。新化合物的结构通过核磁共振光谱确定，对于 3 和 6，也通过单晶 X 射线结构测定确定。