(1aR,2R,2aR,5aS,6S,6aS)-4-phenylhexahydro-3H-2,6-methanooxireno[2,3-f]isoindole-3,5(4H)-dione | 477248-67-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯烷类
• 英文名称: (1aR,2R,2aR,5aS,6S,6aS)-4-phenylhexahydro-3H-2,6-methanooxireno[2,3-f]isoindole-3,5(4H)-dione
• 英文别名: (1S,2S,6R,7R,8R,10S)-4-phenyl-9-oxa-4-azatetracyclo[5.3.1.02,6.08,10]undecane-3,5-dione
• CAS: 477248-67-2
• 化学式: C₁₅H₁₃NO₃
• 分子量: 255.273
• InChiKey: OTEKBPFTWJQPII-BCFCROPCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.21
• 重原子数：
  19.0
• 可旋转键数：
  1.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.47
• 拓扑面积：
  49.91
• 氢给体数：
  0.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  (1aR,2R,2aR,5aS,6S,6aS)-4-phenylhexahydro-3H-2,6-methanooxireno[2,3-f]isoindole-3,5(4H)-dione 在 硫酸 作用下， 反应 8.0h， 生成 2-exo-hydroxy-5-oxo-4-oxatricyclo[4.2.1.0^3,7]nonane-9-carboxylic acid
  参考文献：
  名称：

  摘要：

  Epoxidation of endo- and evo-bicyclo[2.2.1]hept-5-ene-2,3-dicarboxylic acid N-arylimides with a solution of peracetic acid in anhydrous dioxane affords 5,6-exo-epoxybicycloheptanedicarboxylic acid N-arylimides. The epoxidation reaction is not sensitive to the configuration of the imide fragment, to the character and position of the substituent in the aromatic ring. The reaction is determined only by oxidation conditions.

  DOI：

  10.1023/a:1015573902465
• 作为产物：
  描述：

  3,6-endomethylene-1,2,3,6-tetrahydrophthalic anhydride 在 过甲酸 作用下， 以 苯 为溶剂， 反应 36.0h， 生成 (1aR,2R,2aR,5aS,6S,6aS)-4-phenylhexahydro-3H-2,6-methanooxireno[2,3-f]isoindole-3,5(4H)-dione
  参考文献：
  名称：

  Unusual reaction of endic anhydride with 2-methyl-2-phenylaminopropanenitrile

  摘要：

  DOI：

  10.1134/s107042800604021x

文献信息

• Ethanolysis of N-substituted norbornane epoxyimides: Discovery of diverse pathways depending on substituent's character
  作者：Tetyana Petrova、Igor Tarabara、Vitaliy Palchikov、Liliya Kasyan、Dmytro Kosenkov、Sergiy Okovytyy、Leonid Gorb、Svetlana Shishkina、Oleg Shishkin、Jerzy Leszczynski

  DOI：10.1039/b917850c

  日期：——

  In order to understand the vital role of the imide substituent, a systematic theoretical DFT study at the PCM/B3LYP/6-31+G(d) level was carried out. We found that substituents at the nitrogen atom of epoxyimides exerted remarkable effects on the regioselectivity in the ethanolysis reaction, based on the solvent effects and intramolecular electronic interactions. Particularly, the preference for the

  结合实验和理论研究进行了调查的环氧酰亚胺的转变 降冰片烷变成杂环化合物。我们确定了芳基取代的环氧酰亚胺的相互作用降冰片烷 和 乙醇钠导致形成新的杂环化合物，具有制备上有用的产率，并且具有完全的区域选择性。在这种情况下，含有芳基电子给体取代基的环氧酰亚胺的反应导致形成内-9氨基甲酰基-exo -2-羟基-5- oxo-4-氧三环[4.2.1.0 3,7 ]壬烷环氧酰亚胺，exo -2-hydroxy-5-oxo-4-azatricyclo [4.2.1.0 3,7 ] nonan- endo -9-获得羧酸作为乙醇化反应的产物。出乎意料的是，烷基取代的环氧酰亚胺的乙醇化导致二羟基酰亚胺形成为主要产品。为了了解酰亚胺取代基的重要作用，在PCM / B3LYP / 6-31 + G（d）水平进行了系统的理论DFT研究。我们发现，基于溶剂效应和分子内电子相互作用，环氧酰亚胺氮原子上的取代基对乙醇化
• Grignard Reagents and Their <i>N</i> -analogues in the Synthesis of Tricyclic and Tetracyclic Cage-like Lactams
  作者：Igor V. Tkachenko、Igor N. Tarabara、Irina V. Omelchenko、Vitalii A. Palchykov

  DOI：10.1002/jhet.3302

  日期：2018.10

  convenient method is reported for the synthesis of 34 novel tricyclic and tetracyclic cage‐like lactams in high to excellent yields. The method involves treatment of easily available exo‐2,3‐epoxy(or Ts‐aziridino)bicyclo[2.2.1]heptan‐endo‐5,6‐dicarboximides by Grignard reagents, their N‐analogues, or phenyl lithium in tetrahydrofuran. In silico screening of biological activity spectrum showed high probability

  据报道，一种方便的方法可以高产率到优异的产率合成34种新颖的三环和四环笼状内酰胺。该方法包括治疗的容易获得外环氧-2,3-（或TS-氮丙啶基）双环[2.2.1]庚烷内切-5,6-二甲酰亚胺通过格氏试剂，其Ñ -analogues，或苯基锂在四氢呋喃中。在计算机上进行的生物活性谱筛选显示，甘油环醚单加氧酶抑制作用，睾丸酮17β-脱氢酶（NADP +）抑制作用，胆红素氧化酶抑制作用和对四环衍生物的抗缺血活性的发生概率较高。
• exo-2,3-Epoxybicyclo[2.2.1]heptan-endo-5,6-dicarboximides: versatile starting materials for the preparation of oxazaheterocyclic cage compounds
  作者：Vitaliy A. Palchikov、Igor N. Tarabara、Oxana V. Krishchik、Irina V. Omelchenko、Svetlana V. Shishkina、Oleg V. Shishkin、Liliya I. Kasyan

  DOI：10.1007/s00706-014-1192-y

  日期：2014.7

  AbstractA convenient method is reported for the synthesis of N-substituted exo-2-hydroxy-6-aza-4-oxatetracyclo[5.2.1.13,508,9]undecan-7-ones, exo-2-hydroxy-6-aza-4-oxatetracyclo[5.2.1.13,508,9]undecanes, and endo-8,exo-9-dihydroxy-4-azatricyclo[5.2.1.02,6]decanes in high to moderate yields. The method involves treatment of easily available exo-2,3-epoxybicyclo[2.2.1]heptan-endo-5,6-dicarboximides with

  摘要报道了一种方便的方法，用于合成N-取代的exo -2-羟基-6-氮杂-4-草酸酯四环[5.2.1.1 3,5 0 8,9 ] undecan -7-ones，exo -2-羟基-6 -aza-4-oxatetracyclo [5.2.1.1 3,5 0 8,9 ]十一烷和内-8，exo -9-二羟基-4-azatricyclo [5.2.1.0 2,6 ]癸烷，产率高至中等。该方法涉及治疗容易得到的外切-2,3-epoxybicyclo [2.2.1]庚烷内切-5,6-二甲酰亚胺用的LiAlH 4。 图形概要
• Stereochemistry of dihydroxylation of N-arylbicyclo[2.2.1]-hept-5-ene-endo- and -exo-2,3-dicarboximides
  作者：B. T. Bagmanov

  DOI：10.1134/s1070428007110097

  日期：2007.11

  Stereochemistry of the oxidation of N-arylbicyclo[2.2.1]hept-5-ene-endo-and-exo-2,3-dicarboximides at the double bond with peroxyacetic acid generated in situ in the presence of sulfuric acid and with an anhydrous dioxane solution of peroxyacetic acid was studied. In both cases, the reaction was stereospecific, regardless of the substituent in the N-aryl group and configuration of the imide ring, but the reaction direction depended on the presence of water in the system. In the first case, the corresponding trans-5,6-dihydroxy derivatives were formed, while in the second, exo-5,6-epoxy derivatives. The oxidation of N-arylbicyclo[2.2.1]-hept-5-ene-endo-and-exo-2,3-dicarboximides with a solution of potassium permanganate in aqueous acetone gave the corresponding N-aryl-cis-5,6-dihydroxybicyclo[2.2.1]heptane-endo-and-exo-2,3-dicarboximides. The exo,cis,exo and exo,cis,endo configurations of the synthesized compounds were determined by H-1 NMR spectroscopy.
• Spatial arrangement of norbornanedicarboxylic acids N-arylimides
  作者：M. S. Salakhov、B. T. Bagmanov、N. S. Nabiev

  DOI：10.1134/s1070428010110023

  日期：2010.11

  The effect of substituents on the spatial arrangement of norbornane compounds was investigated. Norbornanedicarboxylic acids N-arylimides with OCH(3), Cl, NO(2) groups in the ortho-position of the aromatic ring form as conformational isomers with hindered rotation. The specific spatial isomerism is confirmed by the quantum-chemical calculations.