5-(3-hydroxypropyl)-7-methoxy-2-(3'-methoxy-4'-hydroxyphenyl)-3-benzo[b]furan-carbaldehyde | 135040-83-4

• 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: 5-(3-hydroxypropyl)-7-methoxy-2-(3'-methoxy-4'-hydroxyphenyl)-3-benzo[b]furan-carbaldehyde
• 英文别名: 2-(4-hydroxy-3-methoxyphenyl)-5-(3-hydroxypropyl)-7-methoxybenzofuran-3-carbaldehyde；salvinal；XH-14；2-(4-Hydroxy-3-methoxyphenyl)-5-(3-hydroxypropyl)-7-methoxy-1-benzofuran-3-carbaldehyde
• CAS: 135040-83-4
• 化学式: C₂₀H₂₀O₆
• 分子量: 356.375
• InChiKey: PHJUPBDWRVMJQA-UHFFFAOYSA-N

物化性质

• 熔点：
  77-79 °C
• 沸点：
  572.0±50.0 °C(Predicted)
• 密度：
  1.288±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  26
• 可旋转键数：
  7
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  89.1
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  5-(3-hydroxypropyl)-7-methoxy-2-(3'-methoxy-4'-hydroxyphenyl)-3-benzo[b]furan-carbaldehyde 在 palladium on activated charcoal 盐酸 、 氢气 作用下， 以 四氢呋喃 为溶剂， 反应 12.0h， 以82%的产率得到5-(3-hydroxypropyl)-7-methoxy-3-methyl-2-(3'-methoxy-4'-hydroxyphenyl)benzofuran
  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
• 作为产物：
  描述：

  3-(4-羟基-3-甲氧基苯基)-1-丙醇 在 palladium on activated charcoal 吡啶 、 盐酸 、 N-溴代丁二酰亚胺(NBS) 、 三氟化硼乙醚 、 potassium chloride 、 水 、 氢气 、 溶剂黄146 、 二异丙胺 作用下， 以 四氢呋喃 为溶剂， 反应 21.0h， 生成 5-(3-hydroxypropyl)-7-methoxy-2-(3'-methoxy-4'-hydroxyphenyl)-3-benzo[b]furan-carbaldehyde
  参考文献：
  名称：

  A new synthesis of the benzofuran adenosine antagonist XH-14

  摘要：

  5-(3-HydroxypropyI)-7-methoxy-2-(3'-methoxy-4'-hydroxyphenyl)benzo[b]furan-3-carbaldehyde (XH-14, 1) has been reported to be a potent A(1) adenosine antagonist. We have developed an efficient synthesis of this compound that should prove valuable for further structure-activity studies. The synthesis incorporates optimised methodology for the selective protection of a hydroxyl group and the ortho-bromination of a phenol. (C) 1997 Published by Elsevier Science Ltd.

  DOI：

  10.1016/s0960-894x(97)10173-1

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。
• Naturally occurring benzofuran: isolation, structure elucidation and total synthesis of 5-(3-hydroxypropyl)-7-methoxy-2-(3′-methoxy-4′-hydroxyphenyl)-3-benzo[b]furancarbaldehyde, a novel adenosine A1 receptor ligand isolated from salvia miltiorrhiza bunge (danshen)
  作者：Zhen Yang、Po Ming Hon、Kuk Ying Chui、Zun Le Xu、Hson Mou Chang、Chi Ming Lee、Yu Xin Cui、Henry N.C. Wong、Chi Duen Poon、Bing M. Fung

  DOI：10.1016/s0040-4039(00)78908-8

  日期：1991.4

  A naturally occurring benzofuran, namely 5-(3-hydroxypropyl)-7-methoxy-2-(3′-methoxy-4′-hydroxyphenyl)-3-benzo[b]furancarbaldehyde was isolated from the roots of S. miltiorrhiza Bunge “Danshen”. Its structure was established by means of spectroscopic methods as well as by a total synthesis. Both the natural and the synthetic compounds showed a high potency (IC50 = 17 nM and 10 nM, respectively) in

  从S. miltiorrhiza Bunge的根中分离出天然存在的苯并呋喃，即5-（3-羟丙基）-7-甲氧基-2-（3'-甲氧基-4'-羟基苯基）-3-苯并[ b ]呋喃甲醛。丹参”。它的结构是通过光谱方法以及通过全合成来确定的。天然化合物和合成化合物在牛腺苷A 1放射性配体结合中均显示出高效价（分别为IC 50 = 17 nM和10 nM）。
• CAFFEIC ACID DERIVATIVES FOR ANTI-ANGIOGENESIS
  申请人：Taipei Medical University

  公开号：US20160355493A1

  公开（公告）日：2016-12-08

  The present invention develops a series of methyl caffeate derivatives having biological activity in anti-angiogenesis. The present invention suggests that the compounds of the invention possess inhibiting angiogenesis through regulation of VEGF/VEGFR-2 and its downstream signaling cascades in the vascular endothelial cells (VECs).

  本发明开发了一系列具有抗血管生成生物活性的甲基咖啡酸衍生物。本发明表明，本发明的化合物通过调节血管内皮细胞（VECs）中的VEGF/VEGFR-2及其下游信号级联来抑制血管生成。
• Synthesis of natural products possessing a benzo[b]furan skeleton
  作者：Henning Lütjens、Peter J. Scammells

  DOI：10.1016/s0040-4039(98)01371-9

  日期：1998.9

  A related synthetic strategy has been used to prepare two natural products (XH-14 and ailanthoidol) which possess a benzo[b]furan skeleton. The synthesis of XH-14 involved the use of a palladium-catalyzed cyclization with concomitant carbonylation via insertion of carbon monoxide to introduce regioselectively a formyl group in the 3-position.

  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。
• Revealing the fate of the phenylcoumaran linkage during lignin oxidation reactions
  作者：Ciaran W. Lahive、Christopher S. Lancefield、Anna Codina、Paul C. J. Kamer、Nicholas J. Westwood

  DOI：10.1039/c7ob03087h

  日期：——

  The fate of most lignin linkages, other than the β-O-4, under selective oxidation conditions is largely unknown. In this work we use advanced β-5 lignin model compounds to identify the fate of phenylcoumaran units in a softwood lignin during oxidation with DDQ. By using model compounds combined with detailed characterisation of the oxidised lignin polymer using HSQC and HMBC NMR we show that phenylcoumarones

  在选择性氧化条件下，除β-O-4以外，大多数木质素键的命运是未知的。在这项工作中，我们使用先进的β-5木质素模型化合物来确定DDQ氧化过程中软木木质素中苯香豆素单元的命运。通过使用模型化合物以及使用HSQC和HMBC NMR对氧化木质素聚合物进行详细表征的方法，我们表明苯基香豆酮是一种主要产物，因此构成了氧化木质素中的新型非天然β-5键。此外，这些单元在木质素中的反应性使我们进一步研究了它们在木质素中的连接性，表明它们同时被发现是酚和醚化单元。此处开发的发现和方法将有助于提高选择性氧化木质素解聚工艺的效率，