(+/-)-trans-2-(3,4-dimethoxyphenyl)-2,3-dihydro-5-allyl-6-hydroxy-3-methylbenzofuran | 104265-73-8

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 2-芳基苯并呋喃类黄酮
• 英文名称: (+/-)-trans-2-(3,4-dimethoxyphenyl)-2,3-dihydro-5-allyl-6-hydroxy-3-methylbenzofuran
• 英文别名: rac-(2S,3S)-5-allyl-6-hydroxy-2-(3,4-dimethoxyphenyl)-3-methyl-2,3-dihydrobenzofuran；(+/-)-Liliflol-B；(+/-)-liliflol B；(2S,3S)-2-(3,4-dimethoxyphenyl)-3-methyl-5-prop-2-enyl-2,3-dihydro-1-benzofuran-6-ol
• CAS: 104265-73-8
• 化学式: C₂₀H₂₂O₄
• 分子量: 326.392
• InChiKey: LFHBEUCMTNNMQJ-YUNKPMOVSA-N

物化性质

• 沸点：
  442.0±45.0 °C(Predicted)
• 密度：
  1.146±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.4
• 重原子数：
  24
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  47.9
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (+/-)-trans-2-(3,4-dimethoxyphenyl)-2,3-dihydro-5-allyl-6-hydroxy-3-methylbenzofuran 在 palladium on activated charcoal lead(IV) acetate 、 氢气 作用下， 以 乙酸乙酯 为溶剂， 25.0 ℃ 、137.9 kPa 条件下， 反应 3.5h， 生成 rac-dihydrokadsurenone
  参考文献：
  名称：

  Structure-activity relationships of kadsurenone analogues

  摘要：

  Kadsurenone, a specific receptor antagonist of platelet-activating factor (PAF), and its analogues were prepared from derivatives of cinnamyl alcohol and (allyloxy)phenol. Racemic kadsurenone, resolvable by a Chiralpak column at low temperatures, has an IC50 value of 2 X 10(-7) M, which is about 50% of the activity of the natural product (IC50 = 1 X 10(-7) M). The structural specificity of kadsurenone was further demonstrated by the low PAF-receptor-blocking activities of denudatin B, mirandin A, desallylkadsurenone, and the 2-epimer of kadsurenone.

  DOI：

  10.1021/jm00384a023
• 作为产物：
  描述：

  (E)-3-(3,4-二甲氧基苯基)烯丙醇 在 三苯基膦 、 N,N-二乙基苯胺 、 偶氮二甲酸二乙酯 作用下， 以 四氢呋喃 为溶剂， 反应 13.0h， 生成 (+/-)-trans-2-(3,4-dimethoxyphenyl)-2,3-dihydro-5-allyl-6-hydroxy-3-methylbenzofuran
  参考文献：
  名称：

  Structure-activity relationships of kadsurenone analogues

  摘要：

  Kadsurenone, a specific receptor antagonist of platelet-activating factor (PAF), and its analogues were prepared from derivatives of cinnamyl alcohol and (allyloxy)phenol. Racemic kadsurenone, resolvable by a Chiralpak column at low temperatures, has an IC50 value of 2 X 10(-7) M, which is about 50% of the activity of the natural product (IC50 = 1 X 10(-7) M). The structural specificity of kadsurenone was further demonstrated by the low PAF-receptor-blocking activities of denudatin B, mirandin A, desallylkadsurenone, and the 2-epimer of kadsurenone.

  DOI：

  10.1021/jm00384a023

文献信息

• Ambident Effect of a <i>p</i>-Sulfinyl Group for the Introduction of Two Carbon Substituents to Phenol Rings:  A Convergent Synthesis of Diverse Benzofuran Neolignans
  作者：Shuji Akai、Nobuyoshi Morita、Kiyosei Iio、Yuka Nakamura、Yasuyuki Kita

  DOI：10.1021/ol0001261

  日期：2000.7.1

  A convergent synthesis of diversely substituted benzofuran neolignans (8) is described employing a single p-sulfinyl group on the phenols (3) as an ambident functional group for two types of carbon-carbon bond-forming reactions: (i) the direct synthesis of the dihydrobenzofuran skeletons through an aromatic Pummerer-type reaction and (ii) the ipso-substitution of the sulfur functional group by carbon

  描述了采用多种方式取代的苯并呋喃新木聚糖（8）的收敛合成方法，该方法利用酚（3）上的单个对亚磺酰基作为环境官能团，用于两种类型的碳-碳键形成反应：（i）直接合成二氢苯并呋喃骨架通过芳族Pummerer型反应和（ii）硫官能团通过碳取代基通过配体交换反应进行ipso取代。
• Substituted 2,3,3a,6-tetrahydro-6-oxobenzofuran derivative useful as PAF
  申请人：Merck & Co., Inc.

  公开号：US04704462A1

  公开（公告）日：1987-11-03

  Substituted 2,3,3a,6-tetrahydro-6-oxobenzofuran derivatives have been prepared. These neolignans are found to have potent and specific PAF (Platelet-Activating-Factor) antagonistic activities and thereby useful in the treatment of various diseases or disorders mediated by PAF, for example, pain, fever, inflammation, cardiovascular disorder, asthma, lung edema, allergic disorders, skin diseases, psoriasis, toxic shock syndrome and adult respiratory distress syndrome.

  已制备取代的2,3,3a,6-四氢-6-氧基苯并呋喃衍生物。发现这些新木脂素具有强效且特异的PAF（血小板活化因子）拮抗活性，因此在治疗由PAF介导的各种疾病或紊乱中具有用处，例如疼痛、发热、炎症、心血管紊乱、哮喘、肺水肿、过敏性疾病、皮肤病、牛皮癣、中毒性休克综合征和成人呼吸窘迫综合征。
• Total Synthesis of Two Naturally Occurring Bicyclo[3.2.1]octanoid Neolignans
  作者：Mingyi Wang、Anxin Wu、Xinfu Pan、Hongfang Yang

  DOI：10.1021/jo011077o

  日期：2002.7.1

  first total syntheses of the racemates of naturally occurring macrophyllin-type bicyclo[3.2.1]octanoid neolignans, kadsurenin C 3 and kadsurenin L 4, were accomplished starting from vanillin and resorcinol. The acid-catalyzed rearrangement of hydrobenzofuranoid neolignans into bicyclo[3.2.1]octanoid neolignans was used as the key step.

  从香兰素和间苯二酚开始，完成了天然存在的大叶绿素型双环[3.2.1]类甾体新木脂体外消旋物，kadsurenin C 3和kadsurenin L 4的第一次总合成。关键步骤是将酸催化的氢苯并呋喃类新木脂素重排为双环[3.2.1]辛烷类新木脂素。
• Neolignans from Piper futokadsura
  作者：Michael N. Chang、Gui-Qiu Han、Byron H. Arison、James P. Springer、San-Bao Hwang、Tsung Ying Shen

  DOI：10.1016/s0031-9422(00)83126-x

  日期：1985.1

  Abstract The structures of three new neolignans, kadsurenone, kadsurin A and kadsurin B, isolated from Piper futokadsura were determined by chemical and spectral analysis and X-ray diffraction study. Their biological activities are reported.

  摘要 通过化学和光谱分析以及X 射线衍射研究确定了从Piper futokadsura 中分离的三种新木脂素kadsurenone、kadsurin A 和kadsurin B 的结构。报道了它们的生物活性。
• Stereospecific Lewis Acid-Promoted Reactions of Styrenyl Systems with 2-Alkoxy-(6-Alkyl)-1,4-Benzoquinones: Scope, Limitations, and Synthetic Applications
  作者：Thomas A. Engler、Keith D. Combrink、Michael A. Letavic、Kenneth O. Lynch、James E. Ray

  DOI：10.1021/jo00101a016

  日期：1994.11

  Titanium(IV)-promoted reactions of various (E)-1-propenylbenzenes with 2-methoxy- and 2-methoxy-6-methyl-1,4-benzoquinones produce trans 2-aryl-6-methoxy-3-(and 4-di)methyl-2,3-dihydro-5-benzofuranols (10-12), rel-(1S,6R,7R,8R)-3-methoxy-8-aryl-7-(and 1-di)methylbicyclo[4.2.0]oct-3-ene-2,5-diones (2 + 2 cycloadducts, 13-15) and/or rel-(1R,5R,6R,7R)-7-aryl-3-hydroxy-6-(and 4)methylbicyclo[3.2.1]oct-3-ene-2,8-diones (5 + 2 cycloadducts, 16/17). In many cases, each of the three products can be obtained selectively in good yield by control of reaction conditions and/or by choice of substituents on the quinone or the propenylbenzene. The dihydrobenzofurans are formed stereoselectively, whereas the formation of the bicyclo[4.2.0] systems are stereospecific processes. Thus, reactions of (Z)-1-propenylbenzenes afford rel-(1R,6S,7R,8R)-8-aryl-3-methoxy-7-methylbicyclo[4.2.0]oct-3-ene-2,5-diones (24, 25). No bicyclo[3.2.1]systems. are found in reactions of the (Z)-propenylbenzenes. The products all apparently result from a thermally allowed 2 pi + 4 pi (2 + 5) cycloaddition of the propenylbenzene with a 2-methoxy-4-oxo-2,5-cyclohexadienyl carbocation intermediate (26) formed by coordination of the Ti(IV) to the C-1 carbonyl oxygen of the quinone. In the cycloaddition, the aryl ring of the propenylbenzene occupies an endo position with respect to the pentadienyl carbocation moiety of 26 and the bicyclo[3.2.1] carbocation product of the cycloaddition (28/29) either undergoes dealkylation or rearrangment to yield the observed products. Treatment of the bicylo[4.2.0] systems with protic acid effects their rearrangement to the dihydrobenzofuranols. Reactions of 2-propenylbenzenes and arylcycloalkenes with the quinones regioselectively give dihydrobenzofuranols 43-45 and 49-54, respectively; a 2 + 2 cycloadduct is found in low yield in only one case. The 7-aryl-3-hydroxy-6-methylbicyclo[3.2.1]oct-3-ene-2,8-diones are produced exclusively in reactions of 2-((4-methoxybenzyl)oxy)-1,4-benzoquinones with various propenylbenzenes. Application of these reactions to the synthesis of (+/-)-obtusafuran, (+/-)-liliflol-B, (+/-)-kadsurenone, and (+/-) denudatin are reported.