3-(4-methylphenyl)-2-phenyl-2,3,4,5,6,7-hexahydro-1H-isoindol-1-one | 151830-94-3

• 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-(4-methylphenyl)-2-phenyl-2,3,4,5,6,7-hexahydro-1H-isoindol-1-one
• 英文别名: 3-(4-methylphenyl)-2-phenyl-4,5,6,7-tetrahydro-3H-isoindol-1-one
• CAS: 151830-94-3
• 化学式: C₂₁H₂₁NO
• 分子量: 303.404
• InChiKey: MECJKJIGPIIECF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.4
• 重原子数：
  23
• 可旋转键数：
  2
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  20.3
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  3-(4-methylphenyl)-2-phenyl-2,3,4,5,6,7-hexahydro-1H-isoindol-1-one 在 magnesium 作用下， 以 甲醇 为溶剂， 反应 8.0h， 以40%的产率得到cis-2-phenyl-3-(p-tolyl)-1-oxo-2,3,3a,4,5,6,7,7a-octahydro-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
• 作为产物：
  描述：

  苯胺 、 2-p-toluoylcyclohexanecarboxylic acid 反应 3.0h， 以60%的产率得到3-(4-methylphenyl)-2-phenyl-2,3,4,5,6,7-hexahydro-1H-isoindol-1-one
  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

• Design and synthesis of some isoindoline derivatives as analogues of the active anti-inflammatory Indoprofen
  作者：Ferenc Csende、Ferenc Miklós、Andrea Porkoláb

  DOI：10.3998/ark.5550190.0014.225

  日期：——

  Searching new targets for anti-inflammatory drug de sign, agents with the isoindole skeleton were focused on the basis of preliminary studies of NSAI Ds as COX-1 and/or COX-2 enzyme inhibitors. Thus several novel N-substituted isoindoline derivatives as possible bi ologically active compounds were prepared as analogues of Indoprofen ( 1) starting from cis -2-((4- methylphenyl)carbonyl)cyclohexanecarboxylic

  在 NSAI Ds 作为 COX-1 和/或 COX-2 酶抑制剂的初步研究的基础上，寻找抗炎药物设计的新目标，具有异吲哚骨架的药物。因此，从顺式-2-((4-甲基苯基)羰基)环己烷甲酸(3)开始，通过用伯芳胺处理，制备了几种新的N-取代的异二氢吲哚衍生物作为可能的生物活性化合物作为吲哚洛芬(1)的类似物。
• Csende, Ferenc; Porkolab, Andrea; Matiz, Katalin, Scientia Pharmaceutica, 1999, vol. 67, # 2, p. 149 - 158
  作者：Csende, Ferenc、Porkolab, Andrea、Matiz, Katalin、Szabo, Zoltan、Csorvaassy, Istvan、Frank, Laszlo

  DOI：——

  日期：——
• Synthesis and Structural Study of New Saturated Isoindol-1-one Derivatives
  作者：Ferenc Csende、Zolt� Szab�、G斯a St�er

  DOI：10.3987/com-93-6366

  日期：——

  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.