3,3'-di-O-acetyllamellarin U | 596111-78-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯
• 英文名称: 3,3'-di-O-acetyllamellarin U
• 英文别名: [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-octaen-12-yl)-2-methoxyphenyl] acetate
• CAS: 596111-78-3
• 化学式: C₃₃H₂₉NO₁₀
• 分子量: 599.594
• InChiKey: ZSESJGAJDSRJBY-UHFFFAOYSA-N

物化性质

• 熔点：
  >250 °C(Solvent: Methanol)
• 沸点：
  784.0±60.0 °C(predicted)
• 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)：
  4.8
• 重原子数：
  44
• 可旋转键数：
  9
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.24
• 拓扑面积：
  121
• 氢给体数：
  0
• 氢受体数：
  10

反应信息

• 作为反应物：
  描述：

  3,3'-di-O-acetyllamellarin U 在 2,3-二氯-5,6-二氰基-1,4-苯醌 作用下， 以 二氯甲烷 为溶剂， 反应 18.0h， 以94%的产率得到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
• 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 、 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 49.0h， 生成 3,3'-di-O-acetyllamellarin U
  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

• Gaining diversity in solid-phase synthesis by modulation of cleavage conditions from hydroxymethyl-based supports. Application to lamellarin synthesis
  作者：Pablo Cironi、Carmen Cuevas、Fernando Albericio、Mercedes Álvarez

  DOI：10.1016/j.tet.2004.05.119

  日期：2004.9

  The application of a number of Lewis acids as a cleavage/deprotection method in the solid-phase synthesis of organic molecules can render several analogues, which, after purification, can be submitted for biological evaluation. (C) 2004 Elsevier Ltd. All rights reserved.
• Solid-Phase Total Synthesis of the Pentacyclic System Lamellarins U and L
  作者：Pablo Cironi、Ignacio Manzanares、Fernando Albericio、Mercedes Álvarez

  DOI：10.1021/ol0351192

  日期：2003.8.1

  A total solid-phase synthesis of lamellarins U and L has been achieved. The conversion of an aldehyde group into a formate by a Baeyer-Villiger reaction and a intramolecular [3 + 2] cycloaddition of a 3,4-dihydroisoquinolinium salt over a triple bond comprise the key steps of the process. Each transformation has been controlled with the proper spectroscopic and analytical methods.
• Solid phase synthesis of antitumoral compounds
  申请人：Alvarez Mercedes

  公开号：US20060287529A1

  公开（公告）日：2006-12-21

  Lamellarins are prepared using a solid phase synthesis. In a first aspect, the process includes a step as follows: Formula (I) where R 1 to R 15 are as defined, and X is halogen, provided that one of R 2 , R 3 or R 4 is immobilised to a resin. In a second aspect, the process includes a step as follows: Formula (II) where R 1 ′ to R 5 ′, R 11 ′ and R 13 ′ are as defined, X 1 and X 2 are halogen, M is a metal function and PG is an amino protecting group, provided that one of that R 2 ′, R 3 ′ or R 4 ′ is immobilised to a resin.
• 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.