2-(2,4-Dihydroxy-5-methoxy-phenyl)-8-hydroxy-1-(3-hydroxy-4-methoxy-phenyl)-9-methoxy-5,6-dihydro-pyrrolo[2,1-a]isoquinoline-3-carboxylic acid ethyl ester | 680189-50-8

• 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-(2,4-Dihydroxy-5-methoxy-phenyl)-8-hydroxy-1-(3-hydroxy-4-methoxy-phenyl)-9-methoxy-5,6-dihydro-pyrrolo[2,1-a]isoquinoline-3-carboxylic acid ethyl ester
• 英文别名: Ethyl 2-(2,4-dihydroxy-5-methoxyphenyl)-8-hydroxy-1-(3-hydroxy-4-methoxyphenyl)-9-methoxy-5,6-dihydropyrrolo[2,1-a]isoquinoline-3-carboxylate
• CAS: 680189-50-8
• 化学式: C₃₀H₂₉NO₉
• 分子量: 547.562
• InChiKey: MABBLCFXXHSPQS-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.6
• 重原子数：
  40
• 可旋转键数：
  8
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.23
• 拓扑面积：
  140
• 氢给体数：
  4
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  2-(2,4-Dihydroxy-5-methoxy-phenyl)-8-hydroxy-1-(3-hydroxy-4-methoxy-phenyl)-9-methoxy-5,6-dihydro-pyrrolo[2,1-a]isoquinoline-3-carboxylic acid ethyl ester 在 4-二甲氨基吡啶 、 sodium hydride 、 三乙胺 、 2,3-二氯-5,6-二氰基-1,4-苯醌 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 22.0h， 生成 3,11-bis(acetoxy)-14-(3-acetoxy-4-methoxyphenyl)-2,12-dimethoxy-6H-[1]benzopyrano[4′,3′:4,5]pyrrolo[2,1-a]-isoquinolin-6-one
  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
• 作为产物：
  描述：

  (3-苄氧基-4-甲氧基-苯基)乙酸 在 palladium on activated charcoal 草酰氯 、 氢气 、 碳酸氢钠 、 sodium carbonate 、 N,N-二甲基甲酰胺 、 三氯氧磷 作用下， 以 二氯甲烷 、 水 、 乙酸乙酯 、 N,N-二甲基甲酰胺 、 乙腈 为溶剂， 20.0 ℃ 、517.11 kPa 条件下， 反应 25.0h， 生成 2-(2,4-Dihydroxy-5-methoxy-phenyl)-8-hydroxy-1-(3-hydroxy-4-methoxy-phenyl)-9-methoxy-5,6-dihydro-pyrrolo[2,1-a]isoquinoline-3-carboxylic acid ethyl ester
  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

• Total Synthesis of Lamellarins G, J, L, and Z Using One-Pot Halogen Dance/Negishi Coupling
  作者：Kazuki Morii、Yuto Yasuda、Daiki Morikawa、Atsunori Mori、Kentaro Okano

  DOI：10.1021/acs.joc.1c01505

  日期：2021.10.1

  A bottom-up synthesis of lamellarins G, J, L, and Z was achieved via one-pot halogen dance/Negishi coupling of a lithiated dibromopyrrole derivative. The easily accessible dibromopyrrole bearing an ester moiety underwent halogen dance smoothly at −78 °C within 10 min. The resultant α-pyrrolyllithium was transmetalated to the corresponding organozinc species, which was then coupled with an aryl iodide

  层状蛋白 G、J、L 和 Z 的自下而上合成是通过锂化二溴吡咯衍生物的一锅卤素舞蹈/Negishi 偶联实现的。易于获得的带有酯部分的二溴吡咯在-78°C 下10 分钟内顺利进行了卤素舞蹈。得到的 α-吡咯锂被金属转移到相应的有机锌物质上，然后在催化钯的存在下与芳基碘化物偶联以提供完全取代的吡咯。随后进行卤素 - 锂交换以仅在靠近酯部分的 β 位置掺入硼酸酯基团。这种合成中间体允许逐步二芳基化，用于层状蛋白 G、J、L 和 Z 的全合成。
• A Highly Efficient Synthesis of Lamellarins K and L by the Michael Addition/Ring-Closure Reaction of Benzyldihydroisoquinoline Derivatives with Ethoxycarbonyl-β-nitrostyrenes
  作者：Poonsakdi Ploypradith、Chulabhorn Mahidol、Poolsak Sahakitpichan、Siriporn Wongbundit、Somsak Ruchirawat

  DOI：10.1002/anie.200352043

  日期：2004.2.6