N-(tert-butoxycarbonyl)-4,9[1',2']benzeno-1,3,3a,4,9,9a-hexahydro-1H-benz[f]isoindole | 924626-21-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 蒽
• 英文名称: N-(tert-butoxycarbonyl)-4,9[1',2']benzeno-1,3,3a,4,9,9a-hexahydro-1H-benz[f]isoindole
• CAS: 924626-21-1
• 化学式: C₂₃H₂₅NO₂
• 分子量: 347.457
• InChiKey: DXHBVAMAUOCYSP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.76
• 重原子数：
  26.0
• 可旋转键数：
  0.0
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  29.54
• 氢给体数：
  0.0
• 氢受体数：
  2.0

反应信息

• 作为反应物：
  描述：

  N-(tert-butoxycarbonyl)-4,9[1',2']benzeno-1,3,3a,4,9,9a-hexahydro-1H-benz[f]isoindole 在 4-二甲氨基吡啶 、 四甲基乙二胺 、 仲丁基锂 、 N,N'-二环己基碳二亚胺 、 三氟乙酸 作用下， 以 四氢呋喃 、 二氯甲烷 、 环己烷 为溶剂， 反应 26.0h， 生成 4,9[1',2']benzeno-1,3,3a,4,9,9a-hexahydro-1H-benz[f]isoindole-1-carboxylic acid (-)-menthyl ester
  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 在 palladium dihydroxide lithium aluminium tetrahydride 、 氢气 作用下， 以 四氢呋喃 、 乙醇 为溶剂， 反应 33.0h， 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