cis-3-(3,5-dimethoxyphenyl)-4,6-dimethoxy-2-(4-methoxyphenyl)-2,3-dihydro-1H-inden-1-one

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 二苯乙烯类
• 英文名称: cis-3-(3,5-dimethoxyphenyl)-4,6-dimethoxy-2-(4-methoxyphenyl)-2,3-dihydro-1H-inden-1-one
• 英文别名: (2R,3S)-3-(3,5-dimethoxyphenyl)-4,6-dimethoxy-2-(4-methoxyphenyl)-2,3-dihydroinden-1-one
• 化学式: C₂₆H₂₆O₆
• 分子量: 434.489
• InChiKey: BGQHROFACCVURE-RPWUZVMVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.7
• 重原子数：
  32
• 可旋转键数：
  7
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  63.2
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  cis-3-(3,5-dimethoxyphenyl)-4,6-dimethoxy-2-(4-methoxyphenyl)-2,3-dihydro-1H-inden-1-one 在 potassium carbonate 作用下， 以 甲醇 、 乙腈 为溶剂， 反应 12.0h， 以85%的产率得到3-(3,5-dimethoxyphenyl)-2-hydroxy-4,6-dimethoxy-2-(4-methoxyphenyl)-2,3-dihydro-1H-inden-1-one
  参考文献：
  名称：

  Concise Synthesis of Pauciflorol F Using a Larock Annulation

  摘要：

  A Pd-catalyzed Larock annulation provides expedient access to a subset of resveratrol-derived natural products. The reported approach resulted in the structural revision of an intermediate en route to the natural product pauciflorol F, the total synthesis of which proceeded in two steps from the requisite pentannulation product.

  DOI：

  10.1021/ol902141z
• 作为产物：
  描述：

  3-(3,5-dimethoxyphenyl)-4,6-dimethoxy-2-(4-methoxyphenyl)-1H-inden-1-one 在 palladium 10% on activated carbon 、 氢气 作用下， 以 甲醇 为溶剂， 反应 1.5h， 以78%的产率得到cis-3-(3,5-dimethoxyphenyl)-4,6-dimethoxy-2-(4-methoxyphenyl)-2,3-dihydro-1H-inden-1-one
  参考文献：
  名称：

  Concise Synthesis of Pauciflorol F Using a Larock Annulation

  摘要：

  A Pd-catalyzed Larock annulation provides expedient access to a subset of resveratrol-derived natural products. The reported approach resulted in the structural revision of an intermediate en route to the natural product pauciflorol F, the total synthesis of which proceeded in two steps from the requisite pentannulation product.

  DOI：

  10.1021/ol902141z

文献信息

• Stereoselective Palladium-Catalyzed α-Arylation of 3-Aryl-1-Indanones: An Asymmetric Synthesis of (+)-Pauciflorol F
  作者：Bong Hyang Lee、Young Lok Choi、Seunghoon Shin、Jung-Nyoung Heo

  DOI：10.1021/jo2009164

  日期：2011.8.19

  Highly stereoselective, palladium-catalyzed α-arylation reactions of 3-aryl-1-indanones with aryl bromides are described. The use of sodium tert-butoxide as a base in this process is required to elevate the efficiencies and stereoselectivities of these reactions. The new methodology was successfully applied to a highly efficient route for the asymmetric synthesis of (+)-pauciflorol F.

  描述了3-芳基-1-茚满酮与芳基溴化物的高度立体选择性，钯催化的α-芳基化反应。在该方法中需要使用叔丁醇钠作为碱，以提高这些反应的效率和立体选择性。新方法已成功应用于（+）-二十碳四烯醇F不对称合成的高效途径。
• Asymmetric Synthesis of (+)- and (−)-Pauciflorol F: Confirmation of Absolute Stereochemistry
  作者：Daniel J. Kerr、Michael Miletic、Narasimhulu Manchala、Jonathan M. White、Bernard L. Flynn

  DOI：10.1021/ol401752u

  日期：2013.8.16

  An efficient, formal enantioselective synthesis of (+)- and (−)-pauciflorol F has been achieved using a recently introduced oxazolidinone controlled torquoselective Nazarov reaction. The absolute stereochemistry of pauciflorol F and its biosynthetic precursors has been unambiguously confirmed using X-ray crystallography.

  使用最近引入的恶唑烷酮控制的对甲苯二酚的纳扎罗夫反应，已经实现了对（+）-和（-）-古朴三醇F的高效，正式对映选择性合成。使用X射线晶体学已明确地证实了紫杉醇F及其生物合成前体的绝对立体化学。
• SYNTHESIS OF RESVERATROL-BASED NATURAL PRODUCTS
  申请人：Snyder Scott Alan

  公开号：US20100247462A1

  公开（公告）日：2010-09-30

  Processes for synthesizing resveratrol-based oligomers are provided. In addition, resveratrol-based oligomer compounds free of plant extract are provided.

  提供了合成白藜芦醇基寡聚物的过程。此外，还提供了不含植物提取物的白藜芦醇基寡聚物化合物。
• US9185909B2
  申请人：——

  公开号：US9185909B2

  公开（公告）日：2015-11-17
• [EN] SYNTHESIS OF RESVERATROL-BASED NATURAL PRODUCTS<br/>[FR] SYNTHÈSE DE PRODUITS NATURELS À BASE DE RESVÉRATROL
  申请人：UNIV COLUMBIA

  公开号：WO2009038731A2

  公开（公告）日：2009-03-26

  Processes for synthesizing reveratrol-based oligomers are provided. In addition, reservatrol-based oligomer compounds free of plant extract are provided.