14-(3-acetoxy-4-methoxyphenyl)-3-acetoxy-2,10,11,12-tetramethoxy-6H-chromeno[4',3':4,5]pyrrolo[2,1-a]isoquinolin-6-one | 919082-45-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯
• 英文名称: 14-(3-acetoxy-4-methoxyphenyl)-3-acetoxy-2,10,11,12-tetramethoxy-6H-chromeno[4',3':4,5]pyrrolo[2,1-a]isoquinolin-6-one
• 英文别名: lamellarin W diacetate；[5-(7-Acetyloxy-8,16,17,18-tetramethoxy-3-oxo-4-oxa-1-azapentacyclo[11.8.0.02,11.05,10.014,19]henicosa-2(11),5,7,9,12,14,16,18,20-nonaen-12-yl)-2-methoxyphenyl] acetate
• CAS: 919082-45-4
• 化学式: C₃₄H₂₉NO₁₁
• 分子量: 627.604
• InChiKey: AIVIJQBPWLBJKW-UHFFFAOYSA-N

物化性质

• 熔点：
  215-220 °C(Solvent: Ethyl acetate; Hexane)
• 密度：
  1.37±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  6.2
• 重原子数：
  46
• 可旋转键数：
  10
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.21
• 拓扑面积：
  130
• 氢给体数：
  0
• 氢受体数：
  11

反应信息

• 作为反应物：
  描述：

  14-(3-acetoxy-4-methoxyphenyl)-3-acetoxy-2,10,11,12-tetramethoxy-6H-chromeno[4',3':4,5]pyrrolo[2,1-a]isoquinolin-6-one 在 氢氧化钾 作用下， 以 乙醇 为溶剂， 以72%的产率得到14-(3-hydroxy-4-methoxyphenyl)-3-hydroxy-2,10,11,12-tetramethoxy-6H-chromeno[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：

  2,3,4-三甲氧基苯甲醛 在 palladium on activated charcoal 4-二甲氨基吡啶 、 lithium aluminium tetrahydride 、 氢气 、 sodium hydride 、 碳酸氢钠 、 sodium carbonate 、 溶剂黄146 、 乙二胺 、 三乙胺 、 2,3-二氯-5,6-二氰基-1,4-苯醌 、 三氯氧磷 作用下， 以 四氢呋喃 、 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 51.0h， 生成 14-(3-acetoxy-4-methoxyphenyl)-3-acetoxy-2,10,11,12-tetramethoxy-6H-chromeno[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

文献信息

• Total Synthesis of Natural and Unnatural Lamellarins with Saturated and Unsaturated D-Rings
  作者：Poonsakdi Ploypradith、Thaninee Petchmanee、Poolsak Sahakitpichan、Nichole D. Litvinas、Somsak Ruchirawat

  DOI：10.1021/jo061810h

  日期：2006.12.1

  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.