3,4-bis<(3-methoxyphenyl)methyl>dihydro-2(3H)-furanone | 344564-01-8

• 分子结构分类: 有机化合物 - 木脂素、新木脂素和相关化合物 - 呋喃类木脂素
• 英文名称: 3,4-bis<(3-methoxyphenyl)methyl>dihydro-2(3H)-furanone
• 英文别名: 3,4-bis[(3-methoxyphenyl)methyl]oxolan-2-one
• CAS: 344564-01-8
• 化学式: C₂₀H₂₂O₄
• 分子量: 326.392
• InChiKey: RLYSAJZJSSKQCM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4
• 重原子数：
  24
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.35
• 拓扑面积：
  44.8
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  3,4-bis<(3-methoxyphenyl)methyl>dihydro-2(3H)-furanone 在 三溴化硼 作用下， 生成 (-)-enterolactone
  参考文献：
  名称：

  [EN] SYNTHESIS OF <13>C-LABELLED ESTROGEN ANALOGUES
  [FR] SYNTHESE D'ANALOGUES D'OESTROGENES MARQUES PAR <13>C

  摘要：

  公开号：

  WO2004069774A3
• 作为产物：
  描述：

  4-(3-methoxybenzyl)-2(5H)-furanone 在 六甲基磷酰三胺 、 magnesium 、 lithium diisopropyl amide 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 反应 3.0h， 生成 3,4-bis<(3-methoxyphenyl)methyl>dihydro-2(3H)-furanone
  参考文献：
  名称：

  β-羟基砜的二价阴离子：选择性合成 2(5H)-呋喃酮的新方法和通用方法

  摘要：

  衍生自 β-羟基砜的二价阴离子对多种亲电子试剂具有高度反应性，包括卤代烷、羰基化合物和碘乙酸钠。已经通过使用这些二价阴离子开发了一种方便的 4-烷基-和 5-烷基-2(5H)-呋喃酮合成方法。一种合成反式-3,4-双（3-羟基苄基）二氢-2（3H）-呋喃酮的新方法，这是人类发现的第一种木脂素，通过用Mg-甲醇轻松还原2（5H）-呋喃酮描述。

  DOI：

  10.1246/cl.1983.633

文献信息

• DIANIONS OF β-HYDROXY SULFONES: NEW AND GENERAL APPROACH TO SELECTIVE SYNTHESIS OF 2(5<i>H</i>)-FURANONES
  作者：Kazuhiko Tanaka、Kazuhiko Ootake、Keisuke Imai、Nobuo Tanaka、Aritsune Kaji

  DOI：10.1246/cl.1983.633

  日期：1983.5.5

  electrophiles including alkyl halides, carbonyl compounds, and sodium iodoacetate. A convenient synthetic method for 4-alkyl- and 5-alkyl-2(5H)-furanones has been developed by using these dianions. A new synthetic approach to trans-3,4-bis(3-hydroxybenzyl)dihydro-2(3H)-furanone, the first lignan found in humans, via a facile reduction of 2(5H)-furanone with Mg-methanol is also decribed.

  衍生自 β-羟基砜的二价阴离子对多种亲电子试剂具有高度反应性，包括卤代烷、羰基化合物和碘乙酸钠。已经通过使用这些二价阴离子开发了一种方便的 4-烷基-和 5-烷基-2(5H)-呋喃酮合成方法。一种合成反式-3,4-双（3-羟基苄基）二氢-2（3H）-呋喃酮的新方法，这是人类发现的第一种木脂素，通过用Mg-甲醇轻松还原2（5H）-呋喃酮描述。
• Enantiomerically Enriched α-Borylzinc Reagents by Nickel-Catalyzed Carbozincation of Vinylboronic Esters
  作者：Chenlong Zhang、Weipeng Hu、Gabriel J. Lovinger、Jing Jin、Jingjia Chen、James P. Morken

  DOI：10.1021/jacs.1c05274

  日期：2021.9.8

  In this paper is described a synthesis of enantiomerically enriched, configurationally stable organozinc reagents by catalytic enantioselective carbozincation of a vinylboronic ester. This process furnishes enantiomerically enriched α-borylzinc intermediates that are shown to undergo stereospecific reactions, producing enantioenriched secondary boronic ester products. The properties of the intermediate

  本文描述了通过乙烯基硼酸酯的催化对映选择性碳氧化合成对映体富集、构型稳定的有机锌试剂。该工艺提供了富含对映体的 α-硼锌中间体，这些中间体经证明会发生立体定向反应，从而产生富含对映体的仲硼酸酯产品。探索了中间体α-硼锌试剂的性质，并通过将其应用于(-)-aphanorphine和(-)-enterolactone的合成证明了产物的合成效用。
• Bis-hydroxybenzyl derivatives, processes for their preparation and pharmaceutical composition containing same
  申请人：AKZO N.V.

  公开号：EP0038600A1

  公开（公告）日：1981-10-28

  The invention relates to compounds of the formula's: and salts thereof, in which R, and R2 may be the same or different groups selected from hydroxy, and etherified hydroxy and an esterified hydroxy group, having valuable anti-inflammatory, lipid lowering activities, and immunomodulating properties.

  本发明涉及式的化合物： 及其盐类，其中 R 和 R2 可以是相同或不同的基团，选自羟基、醚化羟基和酯化羟基，具有重要的抗炎、降脂活性和免疫调节特性。
• Neelima; Bhaduri, A. P., Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 1984, vol. 23, # 3, p. 209 - 215
  作者：Neelima、Bhaduri, A. P.

  DOI：——

  日期：——
• Intramolecular Regioselective Insertion into Unactivated Prochiral Carbon−Hydrogen Bonds with Diazoacetates of Primary Alcohols Catalyzed by Chiral Dirhodium(II) Carboxamidates. Highly Enantioselective Total Synthesis of Natural Lignan Lactones
  作者：Jeffrey W. Bode、Michael P. Doyle、Marina N. Protopopova、Qi-Lin Zhou

  DOI：10.1021/jo961607u

  日期：1996.1.1

  Intramolecular insertion into unactivated prochiral C-H bonds of 3-aryl-1-propyl diazoacetates catalyzed by dirhodium(II) tetrakis[methyl 1-(3-phenyl propanoyl)imidazolidin-2-one-4(R or S)-carboxylate], Rh-2(4R-MPPIM)(4) or Rh-2(4S-MPPIM)(4), occurs in 91-96% ee and with virtually complete regiocontrol for the formation of beta-benzyl-gamma-butyrolactones. This methodology has been applied to the total synthesis of dibenzylbutyrolactone lignans (-)- and (+)-enterolactone, (-)- and (+)-hinokinin, and (+)-arctigenin from substituted cinnamic acids in 19-27% overall yields. Aryltetralin lignan (+)-isodeoxypodophyllotoxin was prepared from the reactant 3,4-(methylenedioxy)cinnamic acid in 36% yield overall, and the lactone precursor to (+)-isolauricerisinol was formed in 96.5% ee and 23% yield overall. Applications of the chiral Rh-2(MPPIM)4 catalysts to fully aliphatic systems resulting in the formation of beta-substituted-gamma-butyrolactones with high regiocontrol and with 93-96% ee have demonstrated the generality of this methodology. A model that provides accurate predictions of beta-substituted-gamma-butyrolactone absolute configurations in these asymmetric metal carbene transformations is described.