(R(a),R(a))-4,9-bis-(2-hydroxy-phenyl)-benzo[f]isoindole-1,3-dione | 356541-85-0

• 分子结构分类: 有机化合物 - 木脂素、新木脂素和相关化合物 - 芳基萘木脂素
• 英文名称: (R(a),R(a))-4,9-bis-(2-hydroxy-phenyl)-benzo[f]isoindole-1,3-dione
• 英文别名: (S(a),S(a))-4,9-bis-(2-hydroxy-phenyl)-benzo[f]isoindole-1,3-dione；4,9-bis-(2-hydroxy-phenyl)-benzo[f]isoindole-1,3-dione；4,9-Bis(2-hydroxyphenyl)benzo[f]isoindole-1,3-dione
• CAS: 356541-85-0；356541-92-9；854930-80-6；854930-81-7
• 化学式: C₂₄H₁₅NO₄
• 分子量: 381.387
• InChiKey: PWHGRXAJSVSRDS-UHFFFAOYSA-N

物化性质

• 密度：
  1.417±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.5
• 重原子数：
  29
• 可旋转键数：
  2
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  86.6
• 氢给体数：
  3
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  N-叔丁氧羰基-L-色氨酸 、 (R(a),R(a))-4,9-bis-(2-hydroxy-phenyl)-benzo[f]isoindole-1,3-dione 在 4-二甲氨基吡啶 、 N,N'-二环己基碳二亚胺 作用下， 以 二氯甲烷 为溶剂， 反应 2.0h， 以2.23 g的产率得到(R(a),R(a))-4,9-bis(phenyl-2-yl)-benzo[f]isoindole-1,3-dione [(2S)-2-tert-butoxycarbonylamino-3-(1H-indol-3-yl)]dipropionate
  参考文献：
  名称：

  Efficient chromatographic resolution of a configurationally fragile atropisomeric diphenol via its N-(α)-Boc-tryptophan diesters

  摘要：

  Racemic 4,5-bis-(2-hydroxy-phenyl)-benzo[f]isoindole-1,3-dione 2, an atropisomeric diphenol prone to thermal isomerisation, has been efficiently resolved by conversion into its N-(alpha)-Boc-tryptophan diesters. Easy chromatographic separation of the diastereomeric pair of diesters, followed by ester cleavage under mild conditions gave each enantiomer in good yield and high enantiomeric purity. X-ray diffraction on a single crystal of one of the diastereomeric diesters allowed attribution of the absolute configuration of the stereogenic axes. (C) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2005.03.011
• 作为产物：
  描述：

  4,9-Bis-(2-methoxy-phenyl)-benzo[f]isoindole-1,3-dione 在 三溴化硼 作用下， 以 二氯甲烷 为溶剂， 反应 63.0h， 生成 (R(a),R(a))-4,9-bis-(2-hydroxy-phenyl)-benzo[f]isoindole-1,3-dione
  参考文献：
  名称：

  Solid-State Isomerization of Atropodiastereomers: Effective Diastereoselection through Polymorphic Transformations

  摘要：

  DOI：

  10.1002/1521-3773(20010518)40:10<1926::aid-anie1926>3.0.co;2-3

文献信息

• Efficient chromatographic resolution of a configurationally fragile atropisomeric diphenol via its N-(α)-Boc-tryptophan diesters
  作者：Malek Nechab、Bhavesh M. Panchal、Christian Philouze、Cathy Einhorn、Jacques Einhorn

  DOI：10.1016/j.tetasy.2005.03.011

  日期：2005.5

  Racemic 4,5-bis-(2-hydroxy-phenyl)-benzo[f]isoindole-1,3-dione 2, an atropisomeric diphenol prone to thermal isomerisation, has been efficiently resolved by conversion into its N-(alpha)-Boc-tryptophan diesters. Easy chromatographic separation of the diastereomeric pair of diesters, followed by ester cleavage under mild conditions gave each enantiomer in good yield and high enantiomeric purity. X-ray diffraction on a single crystal of one of the diastereomeric diesters allowed attribution of the absolute configuration of the stereogenic axes. (C) 2005 Elsevier Ltd. All rights reserved.
• Solid-State Isomerization of Atropodiastereomers: Effective Diastereoselection through Polymorphic Transformations
  作者：Cathy Einhorn、André Durif、Marie-Thérèse Averbuch、Jacques Einhorn

  DOI：10.1002/1521-3773(20010518)40:10<1926::aid-anie1926>3.0.co;2-3

  日期：2001.5.18