(+)-(8R,9S,10R,11S)-10,11-dihydroxy-8,9-epoxy-8,9,10,11-tetrahydrodibenzacridine | 140460-98-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 喹啉及其衍生物
• 英文名称: (+)-(8R,9S,10R,11S)-10,11-dihydroxy-8,9-epoxy-8,9,10,11-tetrahydrodibenzacridine
• 英文别名: Ccris 3571；(16R,18S,19R,20S)-17-oxa-13-azahexacyclo[12.9.0.03,12.04,9.015,21.016,18]tricosa-1,3(12),4,6,8,10,13,15(21),22-nonaene-19,20-diol
• CAS: 140460-98-6
• 化学式: C₂₁H₁₅NO₃
• 分子量: 329.355
• InChiKey: YDXYXYWIDOQJHT-BQJUDKOJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  25
• 可旋转键数：
  0
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.19
• 拓扑面积：
  65.9
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  (+/-)-trans-10,11-dihydroxy-10,11-dihydrodibenzyacridine 在 吡啶 、 盐酸 、 sodium hydroxide 、 Amberlite-400 (OH^-) 、 水 、 N-溴代乙酰胺 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 反应 29.75h， 生成 (+)-(8R,9S,10R,11S)-10,11-dihydroxy-8,9-epoxy-8,9,10,11-tetrahydrodibenzacridine
  参考文献：
  名称：

  Synthesis of enantiomerically pure bay-region 10,11-diol 8,9-epoxide diastereomers of the carcinogen dibenz[a,h]acridine

  摘要：

  The present study describes the synthesis and configurational assignment of four enantiomerically pure, bay-region 10,11-diol 8,9-epoxide diastereomers 14-17 of dibenz[a,h]acridine (1) from the corresponding optically pure trans-10,11-dihydroxy-10,11-dihydrodibenz[a,h]acridine enantiomers 6 and 7. Racemic trans-10,11-di-hydroxy-10, 11-dihydrodibenz[a,h]acridine (3) was resolved via its conversion to the diastereomeric bis((-)-methyloxy) esters, separation of the diastereomers by short bed/continuous developing preparative TLC, and finally saponification of the individual diastereomers. Assignment of (10R,11R)-absolute configuration to (-)-trans-10,11-dihydroxy-10,11-dihydrodibenz[a,h]acridine (6) was achieved through the application of exciton circular dichroism technique to the bis[p-(dimethylamino)cinnamic] ester 13 of its tetrahydro analogue 11.

  DOI：

  10.1021/jo00036a006

文献信息

• Synthesis of enantiomerically pure bay-region 10,11-diol 8,9-epoxide diastereomers of the carcinogen dibenz[a,h]acridine
  作者：Subodh Kumar、Panna L. Kole、S. K. Balani、Donald M. Jerina

  DOI：10.1021/jo00036a006

  日期：1992.5

  The present study describes the synthesis and configurational assignment of four enantiomerically pure, bay-region 10,11-diol 8,9-epoxide diastereomers 14-17 of dibenz[a,h]acridine (1) from the corresponding optically pure trans-10,11-dihydroxy-10,11-dihydrodibenz[a,h]acridine enantiomers 6 and 7. Racemic trans-10,11-di-hydroxy-10, 11-dihydrodibenz[a,h]acridine (3) was resolved via its conversion to the diastereomeric bis((-)-methyloxy) esters, separation of the diastereomers by short bed/continuous developing preparative TLC, and finally saponification of the individual diastereomers. Assignment of (10R,11R)-absolute configuration to (-)-trans-10,11-dihydroxy-10,11-dihydrodibenz[a,h]acridine (6) was achieved through the application of exciton circular dichroism technique to the bis[p-(dimethylamino)cinnamic] ester 13 of its tetrahydro analogue 11.