N-(p-methoxybenzyl)-4,9[1',2']benzeno-3a,4,9,9a-tetrahydro-1H-benz[f]isoindole-1,3(2H)-dione | 352344-18-4

• 分子结构分类: 有机化合物 - 木脂素、新木脂素和相关化合物 - 芳基四氢萘木脂素
• 英文名称: N-(p-methoxybenzyl)-4,9[1',2']benzeno-3a,4,9,9a-tetrahydro-1H-benz[f]isoindole-1,3(2H)-dione
• 英文别名: 17-[(4-Methoxyphenyl)methyl]-17-azapentacyclo[6.6.5.02,7.09,14.015,19]nonadeca-2,4,6,9,11,13-hexaene-16,18-dione
• CAS: 352344-18-4
• 化学式: C₂₆H₂₁NO₃
• 分子量: 395.458
• InChiKey: DZSYGLHDPIFQJF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  30
• 可旋转键数：
  3
• 环数：
  7.0
• sp3杂化的碳原子比例：
  0.23
• 拓扑面积：
  46.6
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  N-(p-methoxybenzyl)-4,9[1',2']benzeno-3a,4,9,9a-tetrahydro-1H-benz[f]isoindole-1,3(2H)-dione 在 palladium dihydroxide lithium aluminium tetrahydride 、 氢气 作用下， 以 四氢呋喃 、 乙醇 为溶剂， 反应 27.0h， 生成 N-(tert-butoxycarbonyl)-4,9[1',2']benzeno-1,3,3a,4,9,9a-hexahydro-1H-benz[f]isoindole
  参考文献：
  名称：

  A novel design of roof-shaped anthracene-fused chiral prolines as organocatalysts for asymmetric Mannich reactions

  摘要：

  A new class of artificial anthracene-fused chiral proline catalysts has been synthesized from the Diels-Alder adduct of anthracene and maleic anhydride via lithiation/carboxylation of 6 as a key step. Chiral resolution of racemic amino acids was carried out through the formation of diastereomeric esters with (-)-menthol. The absolute configuration of the chiral amino acid was determined by X-ray crystallographic analysis. The utility of the catalyst was confirmed by effecting asymmetric three-component Mannich reactions between aldehyde, ketone, and amine (yield up to 76%, ee up to 90%). (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2006.11.010
• 作为产物：
  描述：

  dibenzobarallene 、 4-甲氧基苄胺 以 四氢呋喃 为溶剂， 反应 6.0h， 以100%的产率得到N-(p-methoxybenzyl)-4,9[1',2']benzeno-3a,4,9,9a-tetrahydro-1H-benz[f]isoindole-1,3(2H)-dione
  参考文献：
  名称：

  A novel design of roof-shaped anthracene-fused chiral prolines as organocatalysts for asymmetric Mannich reactions

  摘要：

  A new class of artificial anthracene-fused chiral proline catalysts has been synthesized from the Diels-Alder adduct of anthracene and maleic anhydride via lithiation/carboxylation of 6 as a key step. Chiral resolution of racemic amino acids was carried out through the formation of diastereomeric esters with (-)-menthol. The absolute configuration of the chiral amino acid was determined by X-ray crystallographic analysis. The utility of the catalyst was confirmed by effecting asymmetric three-component Mannich reactions between aldehyde, ketone, and amine (yield up to 76%, ee up to 90%). (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2006.11.010

文献信息

• A novel design of roof-shaped anthracene-fused chiral prolines as organocatalysts for asymmetric Mannich reactions
  作者：Aika Sasaoka、Md. Imam Uddin、Ai Shimomoto、Yoshiyasu Ichikawa、Motoo Shiro、Hiyoshizo Kotsuki

  DOI：10.1016/j.tetasy.2006.11.010

  日期：2006.11

  A new class of artificial anthracene-fused chiral proline catalysts has been synthesized from the Diels-Alder adduct of anthracene and maleic anhydride via lithiation/carboxylation of 6 as a key step. Chiral resolution of racemic amino acids was carried out through the formation of diastereomeric esters with (-)-menthol. The absolute configuration of the chiral amino acid was determined by X-ray crystallographic analysis. The utility of the catalyst was confirmed by effecting asymmetric three-component Mannich reactions between aldehyde, ketone, and amine (yield up to 76%, ee up to 90%). (c) 2006 Elsevier Ltd. All rights reserved.