9,10-dimethoxy-1,6,7,11b-tetrahydrobenzo[a]quinolizin-4-one | 910564-24-8

• 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-1,6,7,11b-tetrahydrobenzo[a]quinolizin-4-one
• 英文别名: 9,10-dimethoxy-6,7-dihydro-1H-pyrido[2,1-a]isoquinolin-4(11bH)-one；9,10-Dimethoxy-1,6,7,11b-tetrahydrobenzo[a]quinolizin-4-one
• CAS: 910564-24-8
• 化学式: C₁₅H₁₇NO₃
• 分子量: 259.305
• InChiKey: XRJHLVMBPOUFCL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  19
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.4
• 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-1,6,7,11b-tetrahydrobenzo[a]quinolizin-4-one 在 正丁基锂 、 碘苯二乙酸 、 三氟乙酸 作用下， 以 四氢呋喃 、 正己烷 、 水 、 乙腈 为溶剂， 反应 7.5h， 生成 (2RS,11bRS)-2-formyl-9,10-dimethoxy-1,2,3,6,7,11b-hexahydrobenzo[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
• 作为产物：
  描述：

  tert-butyl 6,7-dimethoxy-3,4-dihydroisoquinoline-2(1H)-carboxylate 在 titanium(IV) isopropylate 、 四甲基乙二胺 、 叔丁基锂 、 三乙胺 、 三氟乙酸 作用下， 以 四氢呋喃 、 二氯甲烷 、 正戊烷 为溶剂， 反应 37.17h， 生成 9,10-dimethoxy-1,6,7,11b-tetrahydrobenzo[a]quinolizin-4-one
  参考文献：
  名称：

  The synthesis and structure revision of NSC-134754

  摘要：

  已成功合成强效HIF途径抑制剂亚氨基嘌呤类似物NSC-134754，并已重新确定其结构。首次通过X射线晶体学确定了NSC-134754的立体化学，并证明只有一个立体异构体对HIF具有活性。

  DOI：

  10.1039/c3cc48189a

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.
• The synthesis and structure revision of NSC-134754
  作者：Jennie A. Hickin、Afshan Ahmed、Katharina Fucke、Margaret Ashcroft、Keith Jones

  DOI：10.1039/c3cc48189a

  日期：——

  The synthesis of emetine analogue NSC-134754, a potent inhibitor of the HIF pathway, has been accomplished and its structure reassigned. The stereochemistry of NSC-134754 has been assigned for the first time using X-ray crystallography and it has been demonstrated that only one diastereoisomer is active against HIF.

  已成功合成强效HIF途径抑制剂亚氨基嘌呤类似物NSC-134754，并已重新确定其结构。首次通过X射线晶体学确定了NSC-134754的立体化学，并证明只有一个立体异构体对HIF具有活性。