ethyl 1-(3,4-dimethoxyphenyl)-2-(2-benzyloxy-4,5-dimethoxyphenyl)-8,9-dimethoxy-5,6-dihydropyrrolo[2,1-a]isoquinoline-3-carboxylate | 858520-96-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯
• 英文名称: ethyl 1-(3,4-dimethoxyphenyl)-2-(2-benzyloxy-4,5-dimethoxyphenyl)-8,9-dimethoxy-5,6-dihydropyrrolo[2,1-a]isoquinoline-3-carboxylate
• 英文别名: ethyl 2-(2-benzyloxy-4,5-dimethoxyphenyl)-8,9-dimethoxy-1-(3,4-dimethoxyphenyl)-5,6-dihydropyrrolo[2,1-a]isoquinoline-3-carboxylate；Ethyl 1-(3,4-dimethoxyphenyl)-2-(4,5-dimethoxy-2-phenylmethoxyphenyl)-8,9-dimethoxy-5,6-dihydropyrrolo[2,1-a]isoquinoline-3-carboxylate
• CAS: 858520-96-4
• 化学式: C₄₀H₄₁NO₉
• 分子量: 679.767
• InChiKey: MJZJMXIKVFSALD-UHFFFAOYSA-N

物化性质

• 沸点：
  778.4±60.0 °C(Predicted)
• 密度：
  1.21±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  7.4
• 重原子数：
  50
• 可旋转键数：
  14
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.28
• 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：

  ethyl 1-(3,4-dimethoxyphenyl)-2-(2-benzyloxy-4,5-dimethoxyphenyl)-8,9-dimethoxy-5,6-dihydropyrrolo[2,1-a]isoquinoline-3-carboxylate 在 palladium on activated charcoal 、 氢气 、 溶剂黄146 、 三乙胺 作用下， 以 乙醇 、 甲醇 为溶剂， 以72%的产率得到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：

  木糖苷G三甲基醚通过烯胺酮中间体的木糖化学启发合成

  摘要：

  已经从原理上可以从木糖化学（木质生物质）来源衍生的前体和溶剂实现了简明的高收率的lamellarin G三甲基醚合成。该路线是相对绿色的，因为一些反应是在没有溶剂或相对温和的溶剂的情况下进行的。另外，避免了产物的色谱纯化，并且仅进行一次水性后处理。合成的新颖性在于用于构建中心吡咯环的烯胺酮的中间体。该产品的总产率是迄今为止报道的最高的。

  DOI：

  10.1021/acs.joc.9b01604
• 作为产物：
  描述：

  (3,4-二甲氧基苯基)乙酰氯 在 碳酸氢钠 、 sodium carbonate 、 三氯氧磷 作用下， 以 二氯甲烷 、 水 、 N,N-二甲基甲酰胺 、 乙腈 为溶剂， 反应 23.0h， 生成 ethyl 1-(3,4-dimethoxyphenyl)-2-(2-benzyloxy-4,5-dimethoxyphenyl)-8,9-dimethoxy-5,6-dihydropyrrolo[2,1-a]isoquinoline-3-carboxylate
  参考文献：
  名称：

  Total Synthesis of Natural and Unnatural Lamellarins with Saturated and Unsaturated D-Rings

  摘要：

  Twenty-eight natural and unnatural lamellarins with either a saturated or an unsaturated D-ring were synthesized according to our developed synthetic route. The key step involved the Michael addition/ring closure (Mi-RC) of the benzyldihydroisoquinoline and alpha-nitrocinnamate derivatives, which provided the 2-carboethoxypyrrole intermediates in moderate to good yields (up to 78% yield). Subsequent hydrogenolysis/lactonization furnished lamellarins with a saturated D-ring in excellent yields (up to 93% yield). DDQ oxidation of the saturated lamellarin acetates led directly to the corresponding unsaturated analogues in 54-95% yield. In addition, only two steps in our developed strategy require column chromatography.

  DOI：

  10.1021/jo061810h

文献信息

• Synthesis of Lamellarin U and Lamellarin G Trimethyl Ether by Alkylation of a Deprotonated α-Aminonitrile
  作者：Johannes C. Liermann、Till Opatz

  DOI：10.1021/jo800467e

  日期：2008.6.1

  1,2,3,4-Tetrahydroisoquinoline-1-carbonitriles can serve as starting materials for the one-pot synthesis of 5,6-dihydropyrrolo[2,1a]isoquinolines and 1-benzyl-3,4-dihydroisoquinolines. The latter compounds were transformed to lamellarin G trimethyl ether and lamellarin U in short reaction sequences. This method allows the introduction of acid-sensitive protecting groups for the phenolic hydroxy functions

  1,2,3,4-四氢异喹啉-1-腈可以用作起始的一锅合成5,6-二氢吡咯并[2,1的材料一]异喹啉和1-苄基-3,4-二氢异喹啉。后面的化合物以短的反应顺序被转化为薄片蛋白G三甲醚和薄片蛋白U。这种方法允许引入用于酚羟基官能团的酸敏感保护基，该保护基在经典的Bischler-Napieralski反应的苛刻条件下会裂解。
• 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.