(E)-3-(4-Dimethylamino-phenyl)-acrylic acid (10R,11R)-10-[(E)-3-(4-dimethylamino-phenyl)-acryloyloxy]-8,9,10,11-tetrahydro-dibenzo[a,h]acridin-11-yl ester | 140380-85-4

• 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: (E)-3-(4-Dimethylamino-phenyl)-acrylic acid (10R,11R)-10-[(E)-3-(4-dimethylamino-phenyl)-acryloyloxy]-8,9,10,11-tetrahydro-dibenzo[a,h]acridin-11-yl ester
• CAS: 140380-85-4
• 化学式: C₄₃H₃₉N₃O₄
• 分子量: 661.8
• InChiKey: WQZICDLQIWECOF-RWESQFFUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8.54
• 重原子数：
  50.0
• 可旋转键数：
  8.0
• 环数：
  7.0
• sp3杂化的碳原子比例：
  0.19
• 拓扑面积：
  71.97
• 氢给体数：
  0.0
• 氢受体数：
  7.0

反应信息

• 作为产物：
  描述：

  ((1R,2S,5R)-2-Isopropyl-5-methyl-cyclohexyloxy)-acetic acid (10R,11R)-10-[2-((1R,2S,5R)-2-isopropyl-5-methyl-cyclohexyloxy)-acetoxy]-8,9,10,11-tetrahydro-dibenzo[a,h]acridin-11-yl ester 在 sodium hydroxide 、 sodium hydride 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 反应 24.5h， 生成 (E)-3-(4-Dimethylamino-phenyl)-acrylic acid (10R,11R)-10-[(E)-3-(4-dimethylamino-phenyl)-acryloyloxy]-8,9,10,11-tetrahydro-dibenzo[a,h]acridin-11-yl ester
  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