(+)-trans-(10R,11R)-dihydroxy-8,9,10,11-tetrahydrodibenzacridine | 140460-91-9

• 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: (+)-trans-(10R,11R)-dihydroxy-8,9,10,11-tetrahydrodibenzacridine
• 英文别名: (-)-trans-(10R,11R)-dihydroxy-10,11-dihydrodibenzacridine；Dibenz(a,h)acridine-10,11-dione, 10,11-dihydro-, trans-；(7R,8R)-2-azapentacyclo[12.8.0.03,12.04,9.015,20]docosa-1(14),2,4(9),5,10,12,15,17,19,21-decaene-7,8-diol
• CAS: 140460-91-9
• 化学式: C₂₁H₁₅NO₂
• 分子量: 313.356
• InChiKey: LDRGXWUVYLIIGY-TZIWHRDSSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  24
• 可旋转键数：
  0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.1
• 拓扑面积：
  53.4
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (+)-trans-(10R,11R)-dihydroxy-8,9,10,11-tetrahydrodibenzacridine 在 间氯过氧苯甲酸 作用下， 以 四氢呋喃 为溶剂， 反应 2.5h， 以84.7%的产率得到(+)-(8R,9S,10S,11R)-10,11-dihydroxy-8,9-epoxy-8,9,10,11-tetrahydrodibenzyacridine
  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
• 作为产物：
  描述：

  (+/-)-trans-10,11-dihydroxy-10,11-dihydrodibenzyacridine 在 吡啶 、 sodium hydroxide 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 反应 24.5h， 生成 (+)-trans-(10R,11R)-dihydroxy-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

• RAY, JAYANTA K.;KAR, GANDHI K.;KARMAKAR, ARUN C., J. ORG. CHEM., 56,(1991) N, C. 2268-2270
  作者：RAY, JAYANTA K.、KAR, GANDHI K.、KARMAKAR, ARUN C.

  DOI：——

  日期：——
• KUMAR, SUBODH, J. ORG . CHEM., 1985, 50, N 17, 3070-3073
  作者：KUMAR, SUBODH

  DOI：——

  日期：——
• 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.