二氢去氢二愈创木基醇 | 28199-69-1

• 物质功能分类: 有机原料 - 醇、酚、酚醇类化合物及衍生物
• 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
• 中文名称: 二氢去氢二愈创木基醇
• 英文名称: 2α,3β-7-O-methylcedrusin
• 英文别名: dihydrodehydrodiconiferyl alcohol；(7S,8R)-dihydrodehydrodiconiferyl alcohol；dehydroconiferyl alcohol；(2S,3R)-dihydrodehydrodiconiferyl alcohol；rel-(2α,3β)-7-O-methylcedrusin；(−)-(7R,8S)-dihydrodehydrodiconiferyl alcohol；(-)-(7S,8R)-dihydrodehydrodiconifery alcohol；(-)-dihydrodehydroconiferyl alcohol；dihydrodehydodiconiferyl alcohol；4-[(2S,3R)-3-(hydroxymethyl)-5-(3-hydroxypropyl)-7-methoxy-2,3-dihydro-1-benzofuran-2-yl]-2-methoxyphenol
• CAS: 28199-69-1
• 化学式: C₂₀H₂₄O₆
• 分子量: 360.407
• InChiKey: SBLZVJIHPWRSQQ-HNAYVOBHSA-N

物化性质

• 沸点：
  540.9±50.0 °C(Predicted)
• 密度：
  1.261±0.06 g/cm3(Predicted)
• 溶解度：
  溶于氯仿、二氯甲烷、乙酸乙酯、DMSO、丙酮等。

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  26
• 可旋转键数：
  7
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  88.4
• 氢给体数：
  3
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  二氢去氢二愈创木基醇 生成 dihydrodehydrodiconiferyl alcohol triacetate
  参考文献：
  名称：

  DA, SILVA MARCELO S.;BARBOSA-FILHO, JOSE M.;YOSHIDA, MASSAYOSHI;GOTTLIEB,+, PHYTOCHEMISTRY, 28,(1989) N2, C. 3477-3482

  摘要：

  DOI：
• 作为产物：
  描述：

  4-[(2S,3R)-2,3-dihydro-3-(hydroxymethyl)-5-(3-hydroxypropyl)-7-(methoxy)benzofuran-1-yl]-2-methoxyphenyl β-D-glucopyranoside 在 β-glucosidase 作用下， 以 various solvent(s) 为溶剂， 反应 2.5h， 以12 mg的产率得到二氢去氢二愈创木基醇
  参考文献：
  名称：

  Neolignan glucosides from Jasminum urophyllum

  摘要：

  A novel neolignan-secoiridoid glucoside, jasurolignoside, and a new neolignan, urolignoside, have been isolated from Jasminum urophyllum. Their structures were elucidated on the basis.of 2D-NMR and chemical methods. (C) 1998 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0031-9422(98)00032-6

文献信息

• Benzo[<i>f</i>][1,2]oxasilepines in the Synthesis of Dihydro[<i>b</i>]benzofuran Neolignans
  作者：Ignacio Rodríguez-García、Sergio García-Muñoz、Leticia Jiménez-González、Míriam Álvarez-Corral、Manuel Muñoz-Dorado

  DOI：10.1055/s-2005-921913

  日期：——

  A short synthesis of neolignans with a dihydrobenzo[b]furan skeleton is described. The strategy is based on a ring-closing metathesis to produce benzo[f][1,2]oxasilepines which are condensed with aromatic aldehydes in a modified Sakurai-Hosomi reaction. Natural dihydrodehydrodiconiferyl alcohol (1) and 3-0-demethyldihydrodehydrodiconiferyl alcohol (2) have been prepared in this way.

  描述了具有二氢苯并 [b] 呋喃骨架的新木脂素的简短合成。该策略基于闭环复分解，以生产苯并[f][1,2] oxasilepines，在改进的Sakurai-Hosomi 反应中与芳香醛缩合。用这种方法制备了天然二氢脱氢二松香醇（1）和3-0-脱甲基二氢脱氢二松香醇（2）。
• A Diastereoselective Route to<i>trans</i>-2-Aryl-2,3-dihydrobenzofurans through Sequential Cross-Metathesis/Isomerization/Allylboration Reactions: Synthesis of Bioactive Neolignans
  作者：Rémy Hemelaere、François Carreaux、Bertrand Carboni

  DOI：10.1002/ejoc.201500019

  日期：2015.4

  anti-homoallylic alcohols allow the synthesis of the desired skeleton in a stereoselective fashion. As an illustration, we used this strategy for the preparation of the dihydrodehydrodiconiferyl alcohol (1a), a natural dihydrobenzofuran neolignan, as well as for a formal synthesis of its O-demethylated derivative 1b. An enantioselective version of this approach employing a chiral phosphoric acid in the

  描述了一种新的高度非对映选择性合成路线，用于反式-2,3-二氢苯并呋喃系统，特别是那些在 C2 位置带有芳基取代基的系统。我们战略的基石是从 2-烯丙基取代的酚和醛开始实施交叉复分解/异构化/烯丙基硼化序列。在分子内 Mitsunobu 环化步骤之后，抗高烯丙醇允许以立体选择性方式合成所需骨架。例如，我们使用这种策略制备了二氢脱氢二松香醇 (1a)，一种天然的二氢苯并呋喃新木脂素，以及其 O-去甲基化衍生物 1b 的正式合成。还研究了在烯丙基硼化步骤中使用手性磷酸的这种方法的对映选择性版本。
• Synthesis of dihydrodehydrodiconiferyl alcohol: the revised structure of lawsonicin
  作者：Junxiu Meng、Tao Jiang、Huma Aslam Bhatti、Bina S. Siddiqui、Sally Dixon、Jeremy D. Kilburn

  DOI：10.1039/b918179b

  日期：——

  Structural revision of lawsonicin, a natural product of Lawsonia alba, is reported based upon comparison of its spectral data with that of the naturally occurring dihydrobenzo[b]furan neolignan (rac)-trans-dihydrodehydrodiconiferyl alcohol, which is found to be identical. A concise synthesis of dihydrodehydrodiconiferyl alcohol, via Rh2[S-DOSP]4-catalysed intramolecular C–H insertion, is described.

  根据与天然存在的二氢苯并[b]呋喃新木质素（rac）-反式-二氢去氢二苯醇的光谱数据比较，报道了天芥菜（Lawsonia alba）天然产物lawsonicin的结构修订。还描述了通过Rh2[S-DOSP]4催化的分子内C-H插入反应合成二氢去氢二苯醇的简洁合成方法。
• Comparative analysis of stilbene and benzofuran neolignan derivatives as acetylcholinesterase inhibitors with neuroprotective and anti-inflammatory activities
  作者：Mina Nagumo、Masayuki Ninomiya、Natsuko Oshima、Tomohiro Itoh、Kaori Tanaka、Atsuyoshi Nishina、Mamoru Koketsu

  DOI：10.1016/j.bmcl.2019.07.026

  日期：2019.9

  Stilbenes and benzofuran neolignans are important groups of plant phenolics therefore they play a significant role in plants and human health. The objective of this study was to investigate the structure-activity relationships of naturally occurring stilbene and benzofuran neolignan derivatives as acetylcholinesterase inhibitors. A series of these compounds were prepared and assessed for their inhibition

  Stilbenes和苯并呋喃新木脂素是植物酚类的重要组成部分，因此它们在植物和人类健康中发挥着重要作用。这项研究的目的是研究天然存在的1,2-二苯乙烯和苯并呋喃新木脂素衍生物作为乙酰胆碱酯酶抑制剂的构效关系。制备了一系列这些化合物，并评估了它们对乙酰胆碱酯酶活性的抑制作用。δ-Viniferin，萜烯反式-脱氢二聚体，pallidol，grossamide和Boehmenan发挥了乙酰胆碱酯酶抑制潜能。几种寡聚化合物可防止t- BHP暴露引起的细胞损伤，并抑制脂多糖/干扰素-γ（LPS /IFNγ）诱导的NO的体外产生。我们的发现凸显了蝶草烯反式-脱氢二聚体，pallidol和boehmenan作为治疗神经退行性疾病的多功能保健品的巨大潜力。
• Synthesis and Biological Evaluation of Dihydrobenzofuran Lignans and Related Compounds as Potential Antitumor Agents that Inhibit Tubulin Polymerization
  作者：Luc Pieters、Stefaan Van Dyck、Mei Gao、Ruoli Bai、Ernest Hamel、Arnold Vlietinck、Guy Lemière

  DOI：10.1021/jm990251m

  日期：1999.12.1

  or ferulic acid methyl esters, followed by derivatization reactions. All compounds were evaluated for potential anticancer activity in an in vitro human disease-oriented tumor cell line screening panel that consisted of 60 human tumor cell lines arranged in nine subpanels, representing diverse histologies. Leukemia and breast cancer cell lines were relatively more sensitive to these agents than were

  通过仿生反应序列获得一系列19种相关的二氢苯并呋喃木脂素和苯并呋喃，该过程涉及对香豆酸，咖啡酸或阿魏酸甲酯的氧化二聚，然后进行衍生化反应。在体外人类疾病导向的肿瘤细胞系筛选小组中评估了所有化合物的潜在抗癌活性，该小组由60个人类肿瘤细胞系组成，分布在9个子面板中，代表了不同的组织学。白血病和乳腺癌细胞系相对于其他细胞系对这些试剂更为敏感。化合物2c和2d，尤其是2b（甲基（E）-3-¿2-（3，4-二羟基苯基）-7-羟基-3-甲氧基羰基-2，3-二氢-1-苯并呋喃-5-基丙-2 -enoate），咖啡酸甲酯的二聚产物，含有3'，4' -二羟苯基部分和二氢苯并呋喃环的7位羟基显示出有希望的活性。2b的平均GI（50）值（抑制50％生长所需的摩尔药物浓度）为0.3 microM。针对三种乳腺癌细胞系，2b的GI（50）值小于10 nM。甲基化，C（3）侧链的双键的还原，甲氧基羰基官能团到伯醇的