2-(3-methoxy-4-hydroxyphenyl)-3-methoxycarbonyl-5-(3-hydroxypropyl)-7-methoxybenzo[b]furan | 70610-22-9

• 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: 2-(3-methoxy-4-hydroxyphenyl)-3-methoxycarbonyl-5-(3-hydroxypropyl)-7-methoxybenzo[b]furan
• 英文别名: 4-[3-(hydroxymethyl)-5-(3-hydroxypropyl)-7-methoxy-1-benzofuran-2-yl]-2-methoxyphenol
• CAS: 70610-22-9
• 化学式: C₂₀H₂₂O₆
• 分子量: 358.391
• InChiKey: XPTDFIBAVHSZED-UHFFFAOYSA-N

物化性质

• 熔点：
  122-123 °C
• 沸点：
  534.9±50.0 °C(Predicted)
• 密度：
  1.285±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  26
• 可旋转键数：
  7
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  92.3
• 氢给体数：
  3
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  2-(3-methoxy-4-hydroxyphenyl)-3-methoxycarbonyl-5-(3-hydroxypropyl)-7-methoxybenzo[b]furan 在 manganese(IV) oxide 作用下， 以 乙酸乙酯 为溶剂， 以87%的产率得到5-(3-hydroxypropyl)-7-methoxy-2-(3'-methoxy-4'-hydroxyphenyl)-3-benzo[b]furan-carbaldehyde
  参考文献：
  名称：

  具有苯并[ b ]呋喃骨架的天然产物的合成

  摘要：

  相关的合成策略已用于制备两种具有苯并[ b ]呋喃骨架的天然产物（XH-14和艾蒽酚）。XH-14的合成涉及使用钯催化的环化反应，同时通过插入一氧化碳进行羰基化以在3位区域选择性引入甲酰基。

  DOI：

  10.1016/s0040-4039(98)01371-9
• 作为产物：
  描述：

  5-溴香兰素 在 palladium on activated charcoal 四氢吡咯 、 吡啶 、 盐酸 、 ammonium hydroxide 、 sodium hydroxide 、 lithium aluminium tetrahydride 、 potassium chloride 、 盐酸羟胺 、 氢气 、 copper(II) sulfate 作用下， 以 四氢呋喃 、 吡啶 、 甲醇 、 水 为溶剂， 反应 60.0h， 生成 2-(3-methoxy-4-hydroxyphenyl)-3-methoxycarbonyl-5-(3-hydroxypropyl)-7-methoxybenzo[b]furan
  参考文献：
  名称：

  Compounds from Danshen. Part 7. Regioselective introduction of carbon-3 substituents to 5-alkyl-7-methoxy-2-phenylbenzo[b]furans: synthesis of a novel adenosine A1 receptor ligand and its derivatives

  摘要：

  By maintaining the balance between the electronic requirements, the stereochemical restrictions as well as the kinetic and thermodynamic factors, the unprecedented regioselective electrophilic aromatic substitution of formyl and nitro groups to carbon-3 of 5-alkyl-7-methoxy-2-phenylbenzo[b]furans have been achieved. Subsequent transformation of the resulting formyl group into methyl, hydroxymethyl, 1-hydroxyethyl, and cyano groups are also described.

  DOI：

  10.1021/jo00052a046

文献信息

• A Novel Strategy for the Synthesis of Benzofuran Skeleton Neolignans:  Application to Ailanthoidol, XH-14, and Obovaten
  作者：Chai-Lin Kao、Ji-Wang Chern

  DOI：10.1021/jo0258960

  日期：2002.9.1

  respectively. 15 and 33 were then cyclized in the presence of either mercury acetate in acetic acid or bromine in chloroform to give 3-chloromercurio- or 3-bromobenzofuran, respectively. The 3-chloromercurio intermediates could be reduced to proton or derivatized to ester or bromide, leading to the synthesis of ailanthoidol, XH-14, and obovaten, respectively. In addition, necleophilic substitution was used

  开发了一种方便且通用的合成苯并呋喃骨架化合物艾蒽酚，XH-14和Obovaten的方法。从香兰素开始，一系列反应以71％的收率得到7。用正丁基锂处理7，然后加入取代的苯甲醛导致形成甲醇11和31。将由11和31氧化而得的取代的二苯甲酮用三甲基甲硅烷基重氮甲烷锂盐处理，分别得到二苯基乙炔15和33。然后在乙酸汞在乙酸中或溴在氯仿中的存在下将15和33环化，分别得到3-氯汞-或3-溴苯并呋喃。3-氯汞中间体可以还原为质子或衍生为酯或溴化物，分别导致合成艾兰醇，XH-14和Obovaten。另外，亲核取代被用于将甲酰基或甲基引入3-溴苯并呋喃衍生物中，从而提供了通往XH-14和Obovaten的替代途径。最终的延伸和脱保护反应以30、15和11％的产率分别提供了所需的艾兰酚，XH-14和obovaten。
• Synthesis and Cytotoxicity of Novel Benzofuran Neolignan Derivatives
  作者：Hua-Fang Fan、Ying-Mei Ren、Xiu-Ling Wu、Qiu-An Wang

  DOI：10.3184/030823410x12709997864719

  日期：2010.4

  A series of 10 related benzofuran neolignan derivatives were obtained by utilising a biomimetic reaction sequence involving oxidative dimerisation of methyl ferulate, followed by derivatisation reactions. The structures of the new compounds were confirmed by 1H NMR, elemental analysis, MS and IR. All compounds were evaluated for their cytotoxic potential against five human cancer cell lines (HL-60

  通过利用涉及阿魏酸甲酯氧化二聚化和衍生化反应的仿生反应序列，获得了一系列 10 种相关的苯并呋喃新木脂素衍生物。新化合物的结构经1H NMR、元素分析、MS和IR确证。通过标准 MTT 方法评估所有化合物对五种人类癌细胞系（HL-60、SMMC-7721、A-549、SK-BR-3 和 PAN-1）的细胞毒性潜力。结果表明，它们中的大多数表现出有效的细胞毒性。
• Synthesis of 2-Substituted 3-Acylbenzo[<i>b</i>]furans via the Palladium Catalysed Carbonylative Cyclisation of <i>ortho</i>-Hydroxytolans
  作者：Henning Lütjens、Peter J. Scammells

  DOI：10.1055/s-1999-2764

  日期：1999.7
• Antileishmanial activity, cytotoxicity and QSAR analysis of synthetic dihydrobenzofuran lignans and related benzofurans
  作者：Sabine Van Miert、Stefaan Van Dyck、Thomas J. Schmidt、Reto Brun、Arnold Vlietinck、Guy Lemière、Luc Pieters

  DOI：10.1016/j.bmc.2004.10.058

  日期：2005.2

  A series of synthetic dihydrobenzofuran lignans and related benzofurans were evaluated for their cytotoxicity in a screening panel consisting of various human tumour cell lines, and for their antiprotozoal activity against L. donovani (axenic amastigotes), chloroquine resistant Plasmodium falciparum (strain K1), Trypanosoma brucei rhodesiense and T. cruzi, and for cytotoxicity on L6 cells. No promising cytotoxicities against human tumour cell lines were observed for newly synthesised compounds, but the dimerisation product of some lipophylic esters of caffeic acid, such as compound 2g, showed a high activity against chloroquine-resistant P. falciparum (strain K1) (IC50 0.43 mug/mL) and L. donovani (axenic amastigotes) (IC50 0.12 mug/mL), which was confirmed in an infected macrophage assay (IC50 0.19 mug/mL). QSAR models for the cytotoxic and antileishmanial activity were, generated using Quasar receptor surface modelling. (C) 2004 Elsevier Ltd. All rights reserved.
• Two new neolignan glycosides from Pittosporum glabratum Lindl.
  作者：Huanxin Zhao、Tiantian Nie、Huanjie Guo、Jun Li、Hong Bai

  DOI：10.1016/j.phytol.2012.01.003

  日期：2012.6

  Two new neolignan glycosides, named pittogoside A (1) and pittogoside B (2) were isolated from the roots of Pittosporum glabratum Lindl. Their structures, including the absolute stereochemistry, were determined on the basis of spectroscopic analysis and chemical evidence, with combination of circular dichroism. (C) 2012 Phytochemical Society of Europe. Published by Elsevier B. V. All rights reserved.