(+/-)-Denudatin-B | 104265-74-9

• 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: (+/-)-Denudatin-B
• 英文别名: (+/-)-denudatin B；rac-denudatin B；denudatin B；(2R,3S,3aS)-2-(3,4-dimethoxyphenyl)-3a-methoxy-3-methyl-5-prop-2-enyl-2,3-dihydro-1-benzofuran-6-one
• CAS: 104265-74-9
• 化学式: C₂₁H₂₄O₅
• 分子量: 356.419
• InChiKey: VDYACOATPFOZIO-DYXDTQHNSA-N

物化性质

• 沸点：
  491.1±45.0 °C(Predicted)
• 密度：
  1.18±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  26
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  54
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (+/-)-Denudatin-B 在 盐酸 、 锌 作用下， 以 四氢呋喃 为溶剂， 以90%的产率得到(+/-)-trans-2-(3,4-dimethoxyphenyl)-2,3-dihydro-5-allyl-6-hydroxy-3-methylbenzofuran
  参考文献：
  名称：

  Biomimetic synthesis of the neolignans kadsurenone, denudatin B, O-methyl-liliflodione, and liliflol B

  摘要：

  Synthesis of (+/-)-kadsurenone (1), (+/-)-denudatin B (2), (+/-)-O-methyl-liliflodione (3a), and (+/-)-liliflol B (14) is described. The key synthetic step is a biomimetic cationic cycloaddition between E- or Z-1,2-dimethoxy-4-propenylbenzene (11) and ortho-quinone monoketal 10. (C) 1999 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(99)01063-1
• 作为产物：
  描述：

  (E)-3-(3,4-二甲氧基苯基)烯丙醇 在 lead(IV) acetate 、 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 14.5h， 生成 (+/-)-Denudatin-B
  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

• 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。
• 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.
• Shizuri, Yoshikazu; Yamamura, Shosuke, Tetrahedron Letters, 1983, vol. 24, # 45, p. 5011 - 5012
  作者：Shizuri, Yoshikazu、Yamamura, Shosuke

  DOI：——

  日期：——
• Total synthesis of kadsurenone and its analogs
  作者：M.M. Ponpipom、B.Z. Yue、R.L. Bugianesi、D.R. Brooker、M.N. Chang、T.Y. Shen

  DOI：10.1016/s0040-4039(00)84004-6

  日期：1986.1
• Structure-activity relationships of kadsurenone analogues
  作者：Mitree M. Ponpipom、Robert L. Bugianesi、David R. Brooker、Bao-zhen Yue、San-bao Hwang、Tsung-ying Shen

  DOI：10.1021/jm00384a023

  日期：1987.1

  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.