14-(3-acetoxy-4-methoxyphenyl)-3-acetoxy-2,11,12-trimethoxy-6H-chromeno[4',3':4,5]pyrrolo[2,1-a]isoquinolin-6-one | 919082-49-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯
• 英文名称: 14-(3-acetoxy-4-methoxyphenyl)-3-acetoxy-2,11,12-trimethoxy-6H-chromeno[4',3':4,5]pyrrolo[2,1-a]isoquinolin-6-one
• 英文别名: lamellarin α diacetate；[5-(7-Acetyloxy-8,16,17-trimethoxy-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: 919082-49-8
• 化学式: C₃₃H₂₇NO₁₀
• 分子量: 597.578
• InChiKey: YXZKVFGQUQNFBB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.2
• 重原子数：
  44
• 可旋转键数：
  9
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  120
• 氢给体数：
  0
• 氢受体数：
  10

反应信息

• 作为反应物：
  描述：

  14-(3-acetoxy-4-methoxyphenyl)-3-acetoxy-2,11,12-trimethoxy-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， 反应 0.08h， 以100%的产率得到3-hydroxy-14-(3-hydroxy-4-methoxyphenyl)-2,11,12-trimethoxy-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 4-二甲氨基吡啶 、 草酰氯 、 氢气 、 sodium hydride 、 碳酸氢钠 、 sodium carbonate 、 三乙胺 、 N,N-二甲基甲酰胺 、 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 67.0h， 生成 14-(3-acetoxy-4-methoxyphenyl)-3-acetoxy-2,11,12-trimethoxy-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