2-[1-(3,4-dimethoxyphenyl)-8,9-dimethoxy-5,6-dihydropyrrolo[2,1-a]isoquinolin-2-yl]-4,5-dimethoxyphenyl ethyl carbonate | 519753-21-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯
• 英文名称: 2-[1-(3,4-dimethoxyphenyl)-8,9-dimethoxy-5,6-dihydropyrrolo[2,1-a]isoquinolin-2-yl]-4,5-dimethoxyphenyl ethyl carbonate
• 英文别名: [2-[1-(3,4-Dimethoxyphenyl)-8,9-dimethoxy-5,6-dihydropyrrolo[2,1-a]isoquinolin-2-yl]-4,5-dimethoxyphenyl] ethyl carbonate
• CAS: 519753-21-0
• 化学式: C₃₃H₃₅NO₉
• 分子量: 589.642
• InChiKey: SGJUNUDCQOLSJH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.9
• 重原子数：
  43
• 可旋转键数：
  12
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  95.8
• 氢给体数：
  0
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  2-[1-(3,4-dimethoxyphenyl)-8,9-dimethoxy-5,6-dihydropyrrolo[2,1-a]isoquinolin-2-yl]-4,5-dimethoxyphenyl ethyl carbonate 在 N-溴代丁二酰亚胺(NBS) 、 叔丁基锂 作用下， 以 四氢呋喃 、 二氯甲烷 、 正戊烷 为溶剂， 生成 14-(3,4-dimethoxyphenyl)-2,3,11,12-tetramethoxy-8,9-dihydro-6H-chromeno[4',3':4,5]pyrrolo[2,1-a]isoquinolin-6-one
  参考文献：
  名称：

  Further developments in the synthesis of lamellarin alkaloids via direct metal–halogen exchange

  摘要：

  Direct metal-halogen exchange of 2-bromopyrrole carbonate derivatives with tert-butyllithium followed by the intramolecular lactonization of the resulting 2-pyrrole anion onto the carbonate provided the corresponding lamellarins in moderate to good yield. The lamellarin framework could be obtained from the direct metal-halogen exchange strategy in a 26-33% overall yield over 5-6 steps. (C) 2003 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(02)02887-3
• 作为产物：
  描述：

  3,4-二甲氧基苯酚 在 三氟化硼乙醚 、 sodium hydride 、 碳酸氢钠 、 benzyltrimethylazanium tribroman-2-uide 作用下， 以 四氢呋喃 、 二氯甲烷 、 乙腈 为溶剂， 生成 2-[1-(3,4-dimethoxyphenyl)-8,9-dimethoxy-5,6-dihydropyrrolo[2,1-a]isoquinolin-2-yl]-4,5-dimethoxyphenyl ethyl carbonate
  参考文献：
  名称：

  Further developments in the synthesis of lamellarin alkaloids via direct metal–halogen exchange

  摘要：

  Direct metal-halogen exchange of 2-bromopyrrole carbonate derivatives with tert-butyllithium followed by the intramolecular lactonization of the resulting 2-pyrrole anion onto the carbonate provided the corresponding lamellarins in moderate to good yield. The lamellarin framework could be obtained from the direct metal-halogen exchange strategy in a 26-33% overall yield over 5-6 steps. (C) 2003 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(02)02887-3

文献信息

• Further developments in the synthesis of lamellarin alkaloids via direct metal–halogen exchange
  作者：Poonsakdi Ploypradith、Wiyada Jinaglueng、Chitkavee Pavaro、Somsak Ruchirawat

  DOI：10.1016/s0040-4039(02)02887-3

  日期：2003.2

  Direct metal-halogen exchange of 2-bromopyrrole carbonate derivatives with tert-butyllithium followed by the intramolecular lactonization of the resulting 2-pyrrole anion onto the carbonate provided the corresponding lamellarins in moderate to good yield. The lamellarin framework could be obtained from the direct metal-halogen exchange strategy in a 26-33% overall yield over 5-6 steps. (C) 2003 Elsevier Science Ltd. All rights reserved.
• Utility of Polymer-Supported Reagents in the Total Synthesis of Lamellarins
  作者：Poonsakdi Ploypradith、Rachel Kirk Kagan、Somsak Ruchirawat

  DOI：10.1021/jo050388m

  日期：2005.6.1

  Four solid-supported reagents have been utilized in the multistep synthesis of lamellarins. The use of Amberlyst A-26 Br-3(-) and polymer bound pyridine hydrobromide perbromide (PVPHP) for keto alpha-bromination of the less studied ortho-substituted acetophenone derivatives selectively furnished the corresponding monobromination products (phenacyl bromide derivatives), which were used directly in condensation reactions with benzyldihydroisoquinoline mediated by Amberlyst A-26 NaCO3-. The 2H-pyrrole carbonates subsequently underwent intramolecular Friedel-Crafts transacylation followed by lactonization to provide the lamellarin skeleton. Alternatively, Amberlyst A-26 NaCO3- effectively served as base in condensation reaction of benzyldihydroisoquinoline with alpha-nitrocinnamate derivatives to provide the corresponding 2-ethoxycarbonyl pyrroles, which smoothly underwent O-debenzylation reaction followed by lactonization to furnish the lamellarin skeleton. The novel Amberlyst-15 mediated lactonization reactions effectively combined the otherwise two separate steps into a single transformation.