(+)(9R,10R)-1,5-dibromo-9,10-dihydro-9,10-ethanoanthracene

• 分子结构分类: 有机化合物 - 苯类化合物 - 蒽
• 英文名称: (+)(9R,10R)-1,5-dibromo-9,10-dihydro-9,10-ethanoanthracene
• 英文别名: (1R,8R)-3,10-dibromotetracyclo[6.6.2.02,7.09,14]hexadeca-2(7),3,5,9(14),10,12-hexaene
• 化学式: C₁₆H₁₂Br₂
• 分子量: 364.079
• InChiKey: BDDHAPDQYAUKLL-VXGBXAGGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.7
• 重原子数：
  18
• 可旋转键数：
  0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  0
• 氢给体数：
  0
• 氢受体数：
  0

反应信息

• 作为产物：
  描述：

  1,5-二溴蒽醌 在 sodium tetrahydroborate 、 sodium hypophosphite 、 potassium iodide 作用下， 以 甲苯 为溶剂， 180.0 ℃ 、8.2 MPa 条件下， 反应 67.0h， 生成 (+)(9R,10R)-1,5-dibromo-9,10-dihydro-9,10-ethanoanthracene
  参考文献：
  名称：

  Syntheses and absolute stereochemistry of chiral 9,10-dihydro-9,10-ethanoanthracenes and their tricarbonylchromium complexes

  摘要：

  Several chiral mono- and disubstituted 9,10-dihydro-9,10-ethanoanthracenes have been prepared from the corresponding anthracenes. Most of them were separated into enantiomers by chromatography on cellulose triacetate (CTA) and their absolute chiralities established by chiroptical comparison (via their CD spectra) with key compounds of known configuration. From the laevorotatory 1,5-dibromo derivative 16 the dextrorotatory dideuterio hydrocarbon (+)(9S, 10S)-20 was obtained.Complexation of 2,6-dimethyl 9,10-dihydro-9,10-ethanoanthracene (+)-25, obtained by enantioselective chromatography on CTA [with its chirality (9R, 10R) deduced from optical comparison with the 2-monomethyl derivative of known configuration], with Cr(CO)6 afforded two mono tricarbonylchromium complexes [endo)+)-26 and exo(+)-27] as well as the bis-exo,endo-complex (+)-28. Configurational assignments (exo, endo) are based on the absorption patterns of the bridge protons in the H-1-NMR spectra.

  DOI：

  10.1007/bf00814140

文献信息

• Syntheses and absolute stereochemistry of chiral 9,10-dihydro-9,10-ethanoanthracenes and their tricarbonylchromium complexes
  作者：Z. Li、A. Werner、K. Schlögl

  DOI：10.1007/bf00814140

  日期：1993.4

  Several chiral mono- and disubstituted 9,10-dihydro-9,10-ethanoanthracenes have been prepared from the corresponding anthracenes. Most of them were separated into enantiomers by chromatography on cellulose triacetate (CTA) and their absolute chiralities established by chiroptical comparison (via their CD spectra) with key compounds of known configuration. From the laevorotatory 1,5-dibromo derivative 16 the dextrorotatory dideuterio hydrocarbon (+)(9S, 10S)-20 was obtained.Complexation of 2,6-dimethyl 9,10-dihydro-9,10-ethanoanthracene (+)-25, obtained by enantioselective chromatography on CTA [with its chirality (9R, 10R) deduced from optical comparison with the 2-monomethyl derivative of known configuration], with Cr(CO)6 afforded two mono tricarbonylchromium complexes [endo)+)-26 and exo(+)-27] as well as the bis-exo,endo-complex (+)-28. Configurational assignments (exo, endo) are based on the absorption patterns of the bridge protons in the H-1-NMR spectra.