(+/-)-trans-2-(3,4-dimethoxyphenyl)-2,3-dihydro-5,6-dimethoxy-3-methylbenzofuran | 104832-93-1

• 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-5,6-dimethoxy-3-methylbenzofuran
• 英文别名: rac-(2S,3S)-5,6-dimethoxy-2-(3,4-dimethoxyphenyl)-3-methyl-2,3-dihydrobenzofuran；(2S,3S)-2-(3,4-dimethoxyphenyl)-5,6-dimethoxy-3-methyl-2,3-dihydro-1-benzofuran
• CAS: 104832-93-1
• 化学式: C₁₉H₂₂O₅
• 分子量: 330.381
• InChiKey: JWQOHGJJVKNCSS-WLRWDXFRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  24
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.37
• 拓扑面积：
  46.2
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  反式-3,4,5-三甲氧基肉桂醇 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 6.0h， 生成 (+/-)-trans-2-(3,4-dimethoxyphenyl)-2,3-dihydro-5,6-dimethoxy-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

• Mechanistic aspects and synthetic applications of the electrochemical and iodobenzene bistrifluoroacetate oxidative 1,3-cycloadditions of phenols and electron-rich styrene derivatives
  作者：Bradley D. Gates、Peter Dalidowicz、Andrew Tebben、Shaopeng Wang、John S. Swenton

  DOI：10.1021/jo00033a040

  日期：1992.3

  Anodic oxidation of p-methoxy-substituted phenols and electron-rich styrene or propenylbenzene derivatives affords in good yield trans-dihydrobenzofurans derived from a formal 1,3-oxidative cycloaddition of the phenol to the styrene derivative. The yield of product in this electrochemical oxidation depends upon the ratio of phenol to styrene derivative, current density, and to a lesser extent the amount of supporting electrolyte. While p-methoxyphenol and 4-methoxy-3-methylphenol give good yields of the dihydrobenzofurans using 1:1 molar ratio of reactants, 3,4-dimethoxyphenol requires a 3-4 molar excess of the styrene derivative for a comparable yield of product. Although 4-methoxy-1-naphthol shows yields comparable to p-methoxyphenol in the anodic cycloaddition reaction, 1- and 2-naphthol gave very low yields of product. Qualitatively, trans- and cis-1,2-dimethoxy-4-propenylbenzene show similar yields in the cycloaddition reaction. Many of these same substrates were examined using iodobenzene bis(trifluoroacetate) as oxidant, and the same products were formed as in the electrochemical oxidations noted above. However, for the reaction of 2-naphthol and 1,2-dimethoxy-4-propenylbenzene the iodobenzene bis(trifluoroacetate) oxidation gave a much better yield of the product. A mechanism involving reaction of a phenoxy radical-styrene radical cation pair is considered and discussed.
• A convergent route to dihydrobenzofuran neolignans via a formal 1,3-cycloaddition to oxidized phenols
  作者：Shaopeng Wang、Bradley D. Gates、John S. Swenton

  DOI：10.1021/jo00006a003

  日期：1991.3

  Oxidation of p-methoxy-substituted phenols with iodobenzene bis-trifluoroacetate in the presence of electron-rich styrene derivatives affords trans-dihydrobenzofurans stereoselectively.
• WANG, SHAOPENG;GATES, BRADLEY D.;SWENTON, JOHN S., J. ORG. CHEM. , 56,(1991) N, C. 1979-1981
  作者：WANG, SHAOPENG、GATES, BRADLEY D.、SWENTON, JOHN S.

  DOI：——

  日期：——
• 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.