(E)-diethyl 2-(3,4-dimethoxybenzylidene)succinate | 58402-11-2

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 肉桂酸及其衍生物
• 英文名称: (E)-diethyl 2-(3,4-dimethoxybenzylidene)succinate
• 英文别名: diethyl (2E)-2-[(3,4-dimethoxyphenyl)methylidene]butanedioate
• CAS: 58402-11-2
• 化学式: C₁₇H₂₂O₆
• 分子量: 322.358
• InChiKey: GPVNAJRRYKNMNQ-UKTHLTGXSA-N

物化性质

• 沸点：
  448.3±45.0 °C(Predicted)
• 密度：
  1.134±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  23
• 可旋转键数：
  10
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.41
• 拓扑面积：
  71.1
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  (E)-diethyl 2-(3,4-dimethoxybenzylidene)succinate 在 吡啶 、 lithium aluminium tetrahydride 、 palladium 10% on activated carbon 、 氢气 、 lithium diisopropyl amide 作用下， 以 四氢呋喃 、 乙醇 、 二氯甲烷 为溶剂， 反应 26.67h， 生成 C₂₉H₃₄O₈S
  参考文献：
  名称：

  从雪绒花根中全合成leoligin

  摘要：

  Leoligin 是一种从雪绒花植物根部分离的四氢呋喃木脂素，由藜芦醛 (2 mol)、琥珀酸二乙酯和 2-甲基-(Z)-2-丁烯酸合成。最初，藜芦醛和琥珀酸二乙酯进行 Stobbe 缩合生成 C6-C5 酸，酯化后，该酸与第二分子藜芦醛缩合生成 2,3,4-三取代的 γ-丁内酯中间体。两个还原步骤产生三醇，其用甲苯磺酰氯闭环形成羟甲基-四氢呋喃，其与 2-甲基-(Z)-2-丁烯酸的酯化生成leoligin。

  DOI：

  10.3184/174751918x15314826114010
• 作为产物：
  描述：

  丁二酸二乙酯 在 氯化亚砜 、 sodium ethanolate 作用下， 反应 7.0h， 生成 (E)-diethyl 2-(3,4-dimethoxybenzylidene)succinate
  参考文献：
  名称：

  从雪绒花根中全合成leoligin

  摘要：

  Leoligin 是一种从雪绒花植物根部分离的四氢呋喃木脂素，由藜芦醛 (2 mol)、琥珀酸二乙酯和 2-甲基-(Z)-2-丁烯酸合成。最初，藜芦醛和琥珀酸二乙酯进行 Stobbe 缩合生成 C6-C5 酸，酯化后，该酸与第二分子藜芦醛缩合生成 2,3,4-三取代的 γ-丁内酯中间体。两个还原步骤产生三醇，其用甲苯磺酰氯闭环形成羟甲基-四氢呋喃，其与 2-甲基-(Z)-2-丁烯酸的酯化生成leoligin。

  DOI：

  10.3184/174751918x15314826114010

文献信息

• Antiviral activity of arylnaphthalene and aryldihydronaphthalene lignans
  作者：Christopher Cow、Carmen Leung、James L Charlton

  DOI：10.1139/v00-059

  日期：2000.5.1

  2-dihydronaphthalene lignans is described. The method makes use of the classic Stobbe condensation followed by regioselective reactions that provide access to both the common and retrolactone lignans, e.g., 2 and 3. A total of 25 compounds, many of which are known natural products, were prepared and their antiviral activity against human cytomegalovirus measured.Key words: lignan, Stobbe, arylnaphthalene

  描述了一种大规模合成 1-芳基萘和 1-芳基-1,2-二氢萘木脂素的实用方法。该方法利用经典的 Stobbe 缩合，然后进行区域选择性反应，提供常见和反内酯木脂素，例如 2 和 3。共制备了 25 种化合物，其中许多是已知的天然产物，并确定了它们的抗病毒活性抗人巨细胞病毒测定。关键词：木脂素，Stobbe，芳基萘，抗病毒。
• Synthesis, anti-virus and anti-tumour activities of dibenzylbutyrolactone lignans and their analogues
  作者：Yamu Xia、Jia You、Yuanyuan Zhang、Zhongliang Su

  DOI：10.3184/030823409x12506792542747

  日期：2009.9

  and seven analogues. Four natural lignans were prepared by this method, and five lignans were synthesised for the first time. The synthesised compounds were evaluated for anti-HIV, anti-HSV, and anti-tumour activities. Results showed that the dibenzylbutyrolactone lignans and their analogues were inactive against HIV Tat transactivation and HSV-1 in vitro, but some compounds displayed significant activity

  已开发出二苄基丁内酯木脂素及其类似物的有效合成。基于胡椒醛或藜芦醛与琥珀酸二乙酯的 Stobbe 缩合，以及与 3,4-亚甲基二氧苄基溴的烷基化反应，得到木脂素的骨架。(±)-二酸用奎宁分解并转化官能团以获得三种苄基丁内酯木脂素和七种类似物。采用该方法制备了4种天然木脂素，首次合成了5种木脂素。对合成的化合物进行了抗 HIV、抗 HSV 和抗肿瘤活性的评估。结果表明，二苄基丁内酯木脂素及其类似物在体外对 HIV Tat 反式激活和 HSV-1 无活性，但一些化合物对 MDA-MB-435 人乳腺癌细胞显示出显着的活性。
• Total Synthesis of Cannabisin B
  作者：Yamu Xia、Huaizheng Zhang、Chenchen Li、Gaochao Dong、Zhen Liu

  DOI：10.3184/174751915x14425727961796

  日期：2015.10

  Cannabisin B, a naturally occurring lignanamide, has been synthesised for the first time in 15% overall yield. The convergent synthesis is based on the Stobbe reaction and Friedel–Crafts alkylation reaction as the C–C bond-forming steps to afford the skeleton of the lignanamide which was then condensed with 4-methoxyphenethylamine to obtain Cannabisin B.

  大麻素 B 是一种天然木质素酰胺，这是首次合成，总收率为 15%。该聚合合成法以 Stobbe 反应和 Friedel-Crafts 烷基化反应作为 C-C 键形成步骤，从而得到木质素酰胺的骨架，然后与 4-甲氧基苯乙胺缩合，得到大麻素 B。
• Acid-Catalyzed Cyclization of 2,3-Dibenzylidenesuccinates:  Synthesis of Lignans (±)-Cagayanin and (±)-Galbulin
  作者：Probal K. Datta、Chi Yau、Timothy S. Hooper、Brigitte L. Yvon、James L. Charlton

  DOI：10.1021/jo0161025

  日期：2001.12.1

  cyclizations of E,E-dibenzylidenesuccinate esters have been developed as an efficient synthetic route to 1-aryl-1,2-dihydronaphthalenes. This reaction has been used in the synthesis of the naturally occurring lignans (+/-)-cagayanin and (+/-)-galbulin.

  E，E-二亚苄基琥珀酸酯的酸催化环化已被开发为合成1-芳基-1，2-二氢萘的有效途径。该反应已用于合成天然木脂素（+/-）-花青素和（+/-）-球蛋白。
• Antiproliferative and apoptotic effects of the oxidative dimerization product of methyl caffeate on human breast cancer cells
  作者：Fabrice Bailly、Robert-Alain Toillon、Olympe Tomavo、Nathalie Jouy、Hubert Hondermarck、Philippe Cotelle

  DOI：10.1016/j.bmcl.2012.11.009

  日期：2013.1

  Caffeic acid derivatives are increasingly regarded as potential oncoprotective that could inhibit both the initiation and progression of cancer. Here we have synthesized seven 1-arylnaphthalene lignans and related compounds and tested their impact on breast cancer cell growth in tissue culture. The product of the oxidative dimerization of methyl caffeate, 1-phenylnaphthalene lignan, was found to induce a strong decrease in breast cancer cell number (IC50 similar to 1 mu M) and was selected for further investigation. Flow cytometry analysis revealed a decrease in cell proliferation and an increase in apoptosis in both MCF-7 and MDA-MB-231 breast cancer cell lines that are representative of the two main categories of breast tumors. The 3,4-dihydroxyphenyl group probably induced the biological activity, as the control compounds lacking it had no effect on breast cancer cells. Together, our data indicate that the oxidative dimerization product of methyl caffeate can inhibit breast cancer cell growth at a concentration adequate for pharmacological use. (C) 2012 Elsevier Ltd. All rights reserved.