9,10-dimethoxy-11b-methyl-1,6,7,11b-tetrahydrobenzo[a]quinolizin-4-one | 62681-54-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 四氢异喹啉
• 英文名称: 9,10-dimethoxy-11b-methyl-1,6,7,11b-tetrahydrobenzo[a]quinolizin-4-one
• 英文别名: 9,10-dimethoxy-11b-methyl-1,6,7,11b-tetrahydro-pyrido[2,1-a]isoquinolin-4-one；9,10-dimethoxy-11b-methyl-6,7-dihydro-1H-benzo[a]quinolizin-4-one
• CAS: 62681-54-3
• 化学式: C₁₆H₁₉NO₃
• 分子量: 273.332
• InChiKey: UWUKKQHXQLDLBS-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  20
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.44
• 拓扑面积：
  38.8
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  9,10-dimethoxy-11b-methyl-1,6,7,11b-tetrahydrobenzo[a]quinolizin-4-one 在 sodium tetrahydroborate 、 正丁基锂 、 碘苯二乙酸 、 叔丁基锂 、 三乙胺 、 三氟乙酸 作用下， 以 四氢呋喃 、 乙醇 、 正己烷 、 二氯甲烷 、 水 、 乙腈 为溶剂， 反应 38.75h， 生成
  参考文献：
  名称：

  Conjugate Additions of Sulfur-Stabilized Anions to Unsaturated Lactams. Synthesis of Polyfunctionalized Benzo[a]quinolizinone Systems

  摘要：

  Conjugate addition reactions of sulfur-stabilized nucleophiles to the delta-lactam unit of tetrahydrobenzo[a]benzoquinolizines have been studied. The stereochemical outcome of the conjugate addition reaction depends on the nature of the substituent at the angular position, thus 2,11b-cis or 2,11b-trans diastereomers could be obtained selectively. The tandem conjugate addition-alkylation also takes place in good yields and with high diastereoselectivity. The polyfunctionalized hexahydrobenzo[a]quinolizinone systems obtained could be further elaborated toward emetine-like structures.

  DOI：

  10.1021/jo060903w
• 作为产物：
  描述：

  9,10-dimethoxy-11b-methyl-2,3,6,7-tetrahydro-1H-pyrido[2,1-a]isoquinolin-4(11bH)-one 在 吡啶 、 双氧水 、 lithium diisopropyl amide 作用下， 以 四氢呋喃 、 正己烷 、 二氯甲烷 为溶剂， 反应 1.67h， 生成 9,10-dimethoxy-11b-methyl-1,6,7,11b-tetrahydrobenzo[a]quinolizin-4-one
  参考文献：
  名称：

  Conjugate Additions of Sulfur-Stabilized Anions to Unsaturated Lactams. Synthesis of Polyfunctionalized Benzo[a]quinolizinone Systems

  摘要：

  Conjugate addition reactions of sulfur-stabilized nucleophiles to the delta-lactam unit of tetrahydrobenzo[a]benzoquinolizines have been studied. The stereochemical outcome of the conjugate addition reaction depends on the nature of the substituent at the angular position, thus 2,11b-cis or 2,11b-trans diastereomers could be obtained selectively. The tandem conjugate addition-alkylation also takes place in good yields and with high diastereoselectivity. The polyfunctionalized hexahydrobenzo[a]quinolizinone systems obtained could be further elaborated toward emetine-like structures.

  DOI：

  10.1021/jo060903w

文献信息

• Conjugate Additions of Sulfur-Stabilized Anions to Unsaturated Lactams. Synthesis of Polyfunctionalized Benzo[<i>a</i>]quinolizinone Systems
  作者：Eva García、Esther Lete、Nuria Sotomayor

  DOI：10.1021/jo060903w

  日期：2006.9.1

  Conjugate addition reactions of sulfur-stabilized nucleophiles to the delta-lactam unit of tetrahydrobenzo[a]benzoquinolizines have been studied. The stereochemical outcome of the conjugate addition reaction depends on the nature of the substituent at the angular position, thus 2,11b-cis or 2,11b-trans diastereomers could be obtained selectively. The tandem conjugate addition-alkylation also takes place in good yields and with high diastereoselectivity. The polyfunctionalized hexahydrobenzo[a]quinolizinone systems obtained could be further elaborated toward emetine-like structures.