14-(3,4-dimethoxyphenyl)-11,12-dimethoxy-8,9-dihydro-6H-chromeno[4',3':4,5]pyrrolo[2,1-a]isoquinolin-6-one

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯
• 英文名称: 14-(3,4-dimethoxyphenyl)-11,12-dimethoxy-8,9-dihydro-6H-chromeno[4',3':4,5]pyrrolo[2,1-a]isoquinolin-6-one
• 英文别名: 12-(3,4-Dimethoxyphenyl)-16,17-dimethoxy-4-oxa-1-azapentacyclo[11.8.0.02,11.05,10.014,19]henicosa-2(11),5,7,9,12,14,16,18-octaen-3-one
• 化学式: C₂₉H₂₅NO₆
• 分子量: 483.521
• InChiKey: GUQIOEPDGPSMEI-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.3
• 重原子数：
  36
• 可旋转键数：
  5
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.21
• 拓扑面积：
  68.2
• 氢给体数：
  0
• 氢受体数：
  6

上下游信息

• 上游原料

  中文名称	英文名称	CAS号	化学式	分子量
  ——	2-(2-Allyloxy-phenyl)-1-(3,4-dimethoxy-phenyl)-8,9-dimethoxy-5,6-dihydro-pyrrolo[2,1-a]isoquinoline-3-carboxylic acid ethyl ester	869544-10-5	C34H35NO7	569.654
  ——	[2-[3-Bromo-1-(3,4-dimethoxyphenyl)-8,9-dimethoxy-5,6-dihydropyrrolo[2,1-a]isoquinolin-2-yl]phenyl] ethyl carbonate	519753-12-9	C31H30BrNO7	608.486
  ——	2-[1-(3,4-dimethoxyphenyl)-8,9-dimethoxy-5,6-dihydropyrrolo[2,1-a]isoquinolin-2-yl]phenyl ethyl carbonate	519753-09-4	C31H31NO7	529.59

反应信息

• 作为产物：
  描述：

  N-(3,4-二甲氧基苯乙基)-2-(3,4-二甲氧基苯基)乙酰胺 在 tin(ll) chloride 、 三氯氧磷 作用下， 以 甲苯 为溶剂， 反应 12.0h， 生成 14-(3,4-dimethoxyphenyl)-11,12-dimethoxy-8,9-dihydro-6H-chromeno[4',3':4,5]pyrrolo[2,1-a]isoquinolin-6-one
  参考文献：
  名称：

  反应性在合成lamellarin和8-氧代小ber碱衍生物中的应用：芳基取代的苯并呋喃-8-氧代小ber碱的光化学性质研究

  摘要：

  观察到二氢异喹啉和3-硝基香豆素之间的独特的差异反应性，并被用于在酸催化或碱促进的条件下有效构建薄片蛋白及其异构体苯并呋喃-8-氧代小ber碱衍生物。此外，发现这些制备的在苯并呋喃部分上带有给电子取代基的芳基取代的苯并呋喃-8-氧代小ber碱衍生物是台式稳定的，但对光敏感，当暴露于可见光下时可发生氧化性开环反应，得到相应的酮产物。在有氧条件下发光。

  DOI：

  10.1016/j.tet.2018.01.042

文献信息

• An efficient synthesis of lamellarin alkaloids: synthesis of lamellarin G trimethyl ether
  作者：Somsak Ruchirawat、Thumnoon Mutarapat

  DOI：10.1016/s0040-4039(00)02222-x

  日期：2001.2

  A general and efficient synthesis of lamellarin alkaloids is described. The synthesis involves the formation of the core pyrrolo[2,1-a]isoquinoline, followed by the formation of the lactone ring.

  描述了薄片蛋白生物碱的一般和有效的合成。合成涉及形成吡咯并[2，1- a ]异喹啉核心，然后形成内酯环。
• Domino Bischler-Napieralski - Michael Reaction and Oxidation - New Route to Coumarin-Pyrrole-Isoquinoline Fused Pentacycles
  作者：Ketan S. Mandrekar、Hari K. Kadam、Santosh G. Tilve

  DOI：10.1002/ejoc.201801244

  日期：2018.12.19

  The pentacyclic lamellarin core divides into four units, which can be connected through N‐alkylation, EDC‐coupling, and domino Bischler–Napieralski – Michael – Oxidation reaction sequences. This concise synthesis of lamellarin scaffolds makes it unique among other routes and highlights its importance in the wide field of lamellarin chemistry.

  五环lamellarin核心分为四个单元，可以通过N烷基化，EDC偶联和多米诺骨牌Bischler–Napieralski – Michael–氧化反应序列进行连接。层状蛋白支架的这种简洁的合成使其在其他途径中独树一帜，并突出了其在层状蛋白化学广泛领域中的重要性。
• Total synthesis of lamellarin G trimethyl ether through enaminone cyclocondensation
  作者：Urtė Šachlevičiūtė、Neringa Kleizienė、Aurimas Bieliauskas、Algirdas Šačkus、Till Opatz

  DOI：10.1039/d3ob00870c

  日期：——

  A synthesis of pyrrolo[2,1-a]isoquinolines based on intramolecular condensation of an enaminone intermediate obtained by C-acylation of an N-alkylated 6,7-dimethoxy-1-methyl-3,4-dihydroisoquinolinium salt was developed. This methodology was further applied to the total synthesis of lamellarin G trimethyl ether from commercially available starting materials compatible with xylochemistry with an overall

  开发了一种基于烯胺酮中间体分子内缩合的吡咯并[2,1- a ]异喹啉的合成方法，该烯胺酮中间体是通过N-烷基化6,7-二甲氧基-1-甲基-3,4-二氢异喹啉鎓盐的C-酰化获得的。该方法进一步应用于从与木化学相容的市售起始材料全合成片层素G三甲醚，基于高藜芦胺，7步总产率为26%。
• 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.