10-methoxy-5,6a,7,8,13,13b-hexahydro-6H-13-aza-indeno[1,2-c]phenanthrene | 934490-23-0

• 分子结构分类: 有机化合物 - 生物碱及其衍生物 - 哈马拉生物碱
• 英文名称: 10-methoxy-5,6a,7,8,13,13b-hexahydro-6H-13-aza-indeno[1,2-c]phenanthrene
• CAS: 934490-23-0
• 化学式: C₂₀H₂₀N₂O
• 分子量: 304.392
• InChiKey: SSMODKQSACMSSP-UHFFFAOYSA-N

物化性质

• 沸点：
  491.5±40.0 °C(Predicted)
• 密度：
  1.28±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.68
• 重原子数：
  23.0
• 可旋转键数：
  1.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  28.26
• 氢给体数：
  1.0
• 氢受体数：
  2.0

反应信息

• 作为反应物：
  描述：

  10-methoxy-5,6a,7,8,13,13b-hexahydro-6H-13-aza-indeno[1,2-c]phenanthrene 在 氨 、 sodium 、 三溴化硼 作用下， 以 二氯甲烷 、 丙酮 为溶剂， 反应 5.0h， 生成 11-Methyl-11,21-diazatetracyclo[12.7.0.03,8.015,20]henicosa-1(14),3,5,7,15(20),16,18-heptaen-17-ol
  参考文献：
  名称：

  Dopamine/serotonin receptor ligands. Part 15: Oxygenation of the benz-indolo-azecine LE 300 leads to novel subnanomolar dopamine D1/D5 antagonists

  摘要：

  Relying on the high affinities of the benz-indolo-azecine LE 300 (1) and the hydroxylated dibenz-azecine LE 404 (2b) for the D-1/D-5 receptor subtypes, we synthesized methoxylated, hydroxylated and an indole-N methylated derivatives of 1 (Fig. 1). Hydroxylation of azecine derivatives is beneficial with regard to the affinities and selectivities for all the dopamine receptor subtypes. The 'serotonin-derived' 3-oxygenated target compounds but not the 11-oxygenated analogues were superior to the unsubstituted LE 300. 11-Methoxy-7,14-dimethyl-6,7,8,9,14,15-hexahydro-5H-indolo[3,2-f[3]bcnzazecine (3e) was found to be the most potent antagonist at D-2/D-3/D-4 and D-5 receptor subtypes (K-i for D-5=0.23 nmol) of all known benz-indolo-azecines. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2006.11.093
• 作为产物：
  描述：

  2-(2-chloro-ethyl)-N-[2-(5-methoxy-1H-indol-3-yl)-ethyl]-benzamide 在 三氯氧磷 、 sodium tetrahydroborate 作用下， 以 乙腈 、 甲醇 为溶剂， 反应 5.0h， 以50%的产率得到10-methoxy-5,6a,7,8,13,13b-hexahydro-6H-13-aza-indeno[1,2-c]phenanthrene
  参考文献：
  名称：

  Dopamine/serotonin receptor ligands. Part 15: Oxygenation of the benz-indolo-azecine LE 300 leads to novel subnanomolar dopamine D1/D5 antagonists

  摘要：

  Relying on the high affinities of the benz-indolo-azecine LE 300 (1) and the hydroxylated dibenz-azecine LE 404 (2b) for the D-1/D-5 receptor subtypes, we synthesized methoxylated, hydroxylated and an indole-N methylated derivatives of 1 (Fig. 1). Hydroxylation of azecine derivatives is beneficial with regard to the affinities and selectivities for all the dopamine receptor subtypes. The 'serotonin-derived' 3-oxygenated target compounds but not the 11-oxygenated analogues were superior to the unsubstituted LE 300. 11-Methoxy-7,14-dimethyl-6,7,8,9,14,15-hexahydro-5H-indolo[3,2-f[3]bcnzazecine (3e) was found to be the most potent antagonist at D-2/D-3/D-4 and D-5 receptor subtypes (K-i for D-5=0.23 nmol) of all known benz-indolo-azecines. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2006.11.093

文献信息

• Synthesis of indolo[2,3-a]quinolizine and hexahydro-1H-indolizino[8,7-b]indole derivatives by cascade condensation, cyclization, and Pictet–Spengler reaction: an application to the synthesis of (±)-harmicine
  作者：Chakrapani Sanaboina、Samaresh Jana、Sridhar Chidara、Balaram Patro、Gajendrasinh Balvantsinh Raolji、Laxminarayana Eppakayala

  DOI：10.1016/j.tetlet.2012.07.044

  日期：2012.9

  Synthesis of indole alkaloid related compounds using Schiff base formation, intramolecular cyclization (or N-alkylation), and Pictet–Spengler reaction as a cascade one pot condensation has been reported. The cascade chemistry has been applied to the synthesis of (±)-harmicine as a key step.

  已经报道了使用席夫碱形成，分子内环化（或N-烷基化）和Pictet-Spengler反应作为级联一锅缩合反应合成吲哚生物碱相关化合物的过程。级联化学已被用作合成（±）-甜菜碱的关键步骤。