methyl (E)-3-<(2R*,3S*)-2,3-dihydro-2-(4-hydroxy-3-methoxyphenyl)-3-hydroxymethyl-7-methoxy-1-benzofuran-5-yl>propenoate | 107296-48-0

• 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: methyl (E)-3-<(2R*,3S*)-2,3-dihydro-2-(4-hydroxy-3-methoxyphenyl)-3-hydroxymethyl-7-methoxy-1-benzofuran-5-yl>propenoate
• 英文别名: methyl (E)-3-[2-(4-hydroxy-3-methoxyphenyl)-3-hydroxymethyl-7-methoxy-2,3-dihydro-1-benzofuran-5-yl]-prop-2-enoate；Methyl (E)-3-[2-(4-hydroxy-3-methoxyphenyl)-3-hydroxymethyl-7-methoxy-2,3-dihydrobenzo[b]furan-5-yl]propenoate；methyl (E)-3-[(2R*,3S*)-2,3-dihydro-2-(4-hydroxy-3-methoxyphenyl)-3-hydroxymethyl-7-methoxy-1-benzofuran-5-yl]propenoate；rel-Methyl (2E)-3-[(2R,3S)-2,3-dihydro-2-(4-hydroxy-3-methoxyphenyl)-3-(hydroxymethyl)-7-methoxy-5-benzofuranyl]-2-propenoate；methyl (E)-3-[(2S,3R)-2-(4-hydroxy-3-methoxyphenyl)-3-(hydroxymethyl)-7-methoxy-2,3-dihydro-1-benzofuran-5-yl]prop-2-enoate
• CAS: 107296-48-0
• 化学式: C₂₁H₂₂O₇
• 分子量: 386.401
• InChiKey: DPDJZJNYBSGDHT-ZTLSKPKQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  28
• 可旋转键数：
  7
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  94.4
• 氢给体数：
  2
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  3,4,5-tris((tert-butyldimethylsilyl)oxy)benzoic acid 、 methyl (E)-3-<(2R*,3S*)-2,3-dihydro-2-(4-hydroxy-3-methoxyphenyl)-3-hydroxymethyl-7-methoxy-1-benzofuran-5-yl>propenoate 在 4-二甲氨基吡啶 、 N,N'-二环己基碳二亚胺 作用下， 以 1,2-二氯乙烷 为溶剂， 反应 6.0h， 以85%的产率得到methyl (E)-3-[2-(4-hydroxy-3-methoxyphenyl)-3-(3,4,5-trihydroxyphenylcarbonyloxymethyl)-7-methoxy-2,3-dihydro-1-benzofuran-5-yl]-prop-2-enoate
  参考文献：
  名称：

  Synthesis of ferulic ester dimers, functionalisation and biological evaluation as potential antiatherogenic and antiplasmodial agents

  摘要：

  Oxidative dimerization of ferulic acid methyl ester afforded dihydrobenzofuran derivative and new linear compound identified by X-ray crystallography. The gallate derivatized dihydrobenzofuran analogue was obtained and all compounds were evaluated for potential antiatherogenic, antiplasmodial (best IC50 = 0.8 mu M) and cytotoxic activities. (c) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2007.06.047
• 作为产物：
  描述：

  methyl (E)-3-[2-(4-hydroxy-3-methoxyphenyl)-7-methoxy-3-methoxycarbonyl-2,3-dihydro-1-benzofuran-5-yl]-prop-2-enoate 在 盐酸 、 lithium aluminium tetrahydride 、 potassium carbonate 作用下， 以 四氢呋喃 、 甲醇 、 乙醚 、 丙酮 为溶剂， 反应 9.0h， 生成 methyl (E)-3-<(2R*,3S*)-2,3-dihydro-2-(4-hydroxy-3-methoxyphenyl)-3-hydroxymethyl-7-methoxy-1-benzofuran-5-yl>propenoate
  参考文献：
  名称：

  Antus, Sandor; Gottsegen, Agnes; Kolonits, Pal, Liebigs Annalen der Chemie, 1989, p. 593 - 594

  摘要：

  DOI：

文献信息

• A New Synthesis of Two Naturally Occurring Dihydrobenzo[b]furan-Type Neolignans of Potential Biological Activity
  作者：László Juhász、Zoltán Dinya、Sándor Antus、Tamás E. Gunda

  DOI：10.1515/znb-2001-0612

  日期：2001.6.1

  A new synthesis of the racemates of two naturally occurring neolignans 1 and 2 was achieved via the 2,3-dihydrobenzo[b]furan derivative 3, starting from the commercially available materials o-vanillin (6) and acetovanillone (9).

  摘要：通过从商业可获得的材料o-香草醛（6）和乙酰香草酮（9）开始，利用2,3-二氢苯并[b]呋喃衍生物3成功地合成了两种天然存在的新木脂素1和2的外消旋体。
• A new approach for the synthesis of naturally occurring dihydrobenzo[b]furan-type neolignans of potential biological activity
  作者：László Juhász、Zoltán Dinya、Sándor Antus、Tamás E Gunda

  DOI：10.1016/s0040-4039(00)00187-8

  日期：2000.4

  A new synthesis of racemic naturally occurring neolignan 1 possessing a PGI2 inducing effect was achieved via the 2,3-dihydrobenzo[b]furan derivative 2, starting from the commercially available materials o-vanillin and acetovanillone.

  通过2,3-二氢苯并[ b ]呋喃衍生物2，从市售材料邻香兰素和乙酰香草醛开始，实现了具有PGI 2诱导作用的外消旋天然存在的新木脂素1的新合成。
• On the absolute structure of optically active neolignans containing a dihydrobenzo[b]furan skeleton
  作者：Mabel S.M. Yuen、Feng Xue、Thomas C.W. Mak、Henry N.C. Wong

  DOI：10.1016/s0040-4020(98)00725-x

  日期：1998.10

  Several optically pure neolignans containing a dihydrobenzo[b]furan skeleton were synthesized. Based on an X-ray crystallographic study and circular dichroism results, the absolute configurations of some naturally occurring neolignans, namely balanophonin (1), PGI(2) inducer (2), dehydrodiconiferyl alcohol-4-beta-D-glucoside (3), dehydroconiferyl alcohol (4) and 3',4-di-O-methyicedrusin (5) have been unambiguously established. (C) 1998 Elsevier Science Ltd. All rights reserved.
• Antus, Sandor; Gottsegen, Agnes; Kolonits, Pal, Liebigs Annalen der Chemie, 1989, p. 593 - 594
  作者：Antus, Sandor、Gottsegen, Agnes、Kolonits, Pal、Wagner, Hildebert

  DOI：——

  日期：——
• Synthesis of ferulic ester dimers, functionalisation and biological evaluation as potential antiatherogenic and antiplasmodial agents
  作者：D.L.A. Rakotondramanana、Mélanie Delomenède、Michel Baltas、Hubert Duran、Florence Bedos-Belval、Philippe Rasoanaivo、Anne Negre-Salvayre、Heinz Gornitzka

  DOI：10.1016/j.bmc.2007.06.047

  日期：2007.9

  Oxidative dimerization of ferulic acid methyl ester afforded dihydrobenzofuran derivative and new linear compound identified by X-ray crystallography. The gallate derivatized dihydrobenzofuran analogue was obtained and all compounds were evaluated for potential antiatherogenic, antiplasmodial (best IC50 = 0.8 mu M) and cytotoxic activities. (c) 2007 Elsevier Ltd. All rights reserved.