3,4-dimethoxystilbene | 1466-17-7

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 二苯乙烯类
• 英文名称: 3,4-dimethoxystilbene
• 英文别名: 1,2-Dimethoxy-4-(2-phenylethenyl)benzene
• CAS: 1466-17-7
• 化学式: C₁₆H₁₆O₂
• 分子量: 240.302
• InChiKey: BSHIPXLJHQKYFU-UHFFFAOYSA-N

物化性质

• 熔点：
  111 °C
• 沸点：
  369.0±11.0 °C(Predicted)
• 密度：
  1.089±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  18
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  18.5
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  3,4-dimethoxystilbene 在 对苯二腈 、 氨 作用下， 以 水 、 乙腈 为溶剂， 反应 20.0h， 以21%的产率得到α-phenyl-β-(3,4-dimethoxy)phenethylamine
  参考文献：
  名称：

  Regiochemistry on photoamination of stilbene derivatives with ammonia via electron transfer

  摘要：

  The regiochemistry of photoamination of 1,2-diarylethene (1) with ammonia in the presence of p-dicyanobenzene (DCNB) has been investigated. The photoamination of stilbene and p,p'-dimethoxystilbene gave 1-amino-1,2-diphenylethane and 1-amino-1,2-bis(p-methoxyphenyl)ethane, respectively. The photoamination of unsymmetric 1-aryl-2-phenylethene having an alkoxy group on the para position occurred selectively to give 1-amino-2-aryl-1-phenylethane. On the other hand, the photoamination of 1-aryl-2-phenylethene having a methyl and chloro group on the para position or methoxy group on the meta and ortho positions gave both 1-amino-2-aryl-1-phenylethane and 1-amino-1-aryl-2-phenylethane. The regiochemistry is related with the distribution of positive charge in the cation radicals of 1 generated from photochemical electron transfer to DCNB.

  DOI：

  10.1021/jo00031a010
• 作为产物：
  描述：

  3,4-二甲氧基苄氯 在 sodium hydride 作用下， 以 四氢呋喃 、 甲苯 为溶剂， 反应 6.0h， 生成 3,4-dimethoxystilbene
  参考文献：
  名称：

  Design, synthesis and antitumour and anti-angiogenesis evaluation of 22 moscatilin derivatives

  摘要：

  Two series of moscatilin derivatives were designed, synthesized and evaluated as anti-tumor and anti-angiogenesis agents. Most of these compounds showed moderate-to-obvious cytotoxicity against five cancer cell lines (A549, HepG2, MDA-MB-231, MKN-45, HCT116). Among these cell lines, compounds had obvious effects on HCT116. Especially for 8Ae, the IC50 was low to 0.25 mu M. 8Ae can inhibit the viability and induce the apoptosis of HCT116 cells but exhibit no cytotoxic activity in noncancerous NCM460 colon cells. 8Ae can also arrest the G2/M cell cycle in HCT116 cells by inhibiting the alpha-tubulin expression. Zebrafish bioassay-guided screen showed the 22 moscatilin derivatives had potent anti-angiogenic activities and compound 8Ae had better activities than positive compound. Molecular docking indicated 8Ae interacted with tubulin at the affinity of -7.2 Kcal/mol. In conclusion, compound 8Ae was a potential antitumor and anti-angiogenesis candidate for further development.

  DOI：

  10.1016/j.bmc.2019.04.027

文献信息

• A Simple Route to New Phenanthro- and Phenanthroid-Fused Thiazoles by a PIFA-Mediated (Hetero)biaryl Coupling Reaction
  作者：Isabel Moreno、Imanol Tellitu、Esther Domínguez、Raúl SanMartín

  DOI：10.1002/1099-0690(200207)2002:13<2126::aid-ejoc2126>3.0.co;2-a

  日期：2002.7

  An application of the PIFA-mediated [PIFA: phenyliodine(III) bis(trifluoroacetate)] biaryl coupling reaction is presented and extended to the formation of heterobiaryl connections. A preliminary study of the scope and limitations of this procedure was carried out in the synthesis of phenanthroids 11 from a series of phenethyl-substituted heterocycles 10. It was observed that in some cases a competitive

  提出了 PIFA 介导的 [PIFA: 苯基碘 (III) 双 (三氟乙酸酯)] 联芳基偶联反应的应用，并将其扩展到形成杂联芳基连接。在从一系列苯乙基取代的杂环 10 合成拟类化合物 11 时，对该程序的范围和局限性进行了初步研究。观察到在某些情况下发生了竞争性二聚化过程。还发现，如果芳环与 1,2-二芳基乙烷骨架稠合，则偶联步骤可以有效地扩展到更多的实例，如 23 和 30。一系列 4,5-的合成因此，进行二芳基噻唑 23a-g 以探索 PIFA 介导的非酚类偶联反应的电子要求和区域选择性。当将相同的程序应用于芳基-杂芳基噻唑 30 时，以良好的总产率获得了一系列菲类稠合的噻唑 31。据我们所知，以前没有报道过这种类型的氧化芳基-杂芳基偶联反应。(© Wiley-VCH Verlag GmbH, 69451 Weinheim, Germany, 2002)
• A Bifunctional Iron Nanocomposite Catalyst for Efficient Oxidation of Alkenes to Ketones and 1,2-Diketones
  作者：Tao Song、Zhiming Ma、Peng Ren、Youzhu Yuan、Jianliang Xiao、Yong Yang

  DOI：10.1021/acscatal.9b05197

  日期：2020.4.17

  sites of Fe–Nx and Fe phosphate, as oxidation and Lewis acid sites, were simultaneously integrated into a hierarchical N,P-dual doped porous carbon. As a bifunctional catalyst, it exhibited high efficiency for direct oxidative cleavage of alkenes into ketones or their oxidation into 1,2-diketones with a broad substrate scope and high functional group tolerance using TBHP as the oxidant in water under

  我们在此报告了一种双功能铁纳米复合催化剂的制备，其中两个Fe–N x催化活性位点磷酸铁和铁的氧化位和路易斯酸位同时被整合到一个分层的N，P-双掺杂多孔碳中。作为一种双功能催化剂，它具有良好的催化作用，可在较温和的反应条件下使用TBHP作为氧化剂，将烯烃直接氧化裂解为酮或将其氧化为1,2-二酮，具有广泛的底物范围，并具有较高的官能团耐受性。此外，可以很容易地将其回收以进行后续回收，而不会造成明显的活性损失。机理研究表明，烯烃的直接氧化是通过形成环氧化物作为中间体，然后进行酸催化的Meinwald重排而产生的，该酮的碳原子短了一个或亲核开环，从而以级联方式生成1,2-二酮。
• Substituted CIS- and trans-stilbenes as therapeutic agents
  申请人：Vander Jagt David L.

  公开号：US20070249647A1

  公开（公告）日：2007-10-25

  The present invention relates to method(s) of treating a subject afflicted with cancer or a precancerous condition, an inflammatory disease or condition, and/or stroke or other ischemic disease or condition, the method comprising administering to the subject or patient in need a composition comprising a therapeutically effective amount of a substituted cis or trans-stilbene.

  本发明涉及治疗患有癌症或癌前病变、炎症性疾病或病情以及中风或其他缺血性疾病或病情的方法，该方法包括向需要的受试者或患者施用含有一定治疗有效量的取代的顺式或反式-芪的组合物。
• Synthesis of 4-Nitrophenyl Sulfones and Application in the Modified Julia Olefination
  作者：Jieping Zhu、Daniela Mirk、Jean-Marie Grassot

  DOI：10.1055/s-2006-939682

  日期：——

  4-Nitrophenyl (NP) sulfones were successfully employed in the modified Julia olefination reaction with carbonyl compds. The olefination reaction proceeds through a sequence of aldol addn., Smiles rearrangement, and elimination. The sulfones are easily prepd. in high yields in a two-step sequence starting from inexpensive com. available para-fluoronitrobenzenes via nucleophilic arom. substitution by

  4-硝基苯基 (NP) 砜成功地用于与羰基化合物的改性 Julia 烯化反应。烯化反应通过羟醛加成、Smiles 重排和消除的顺序进行。砜很容易制备。从廉价的 com 开始，以两步顺序高产。可通过亲核芳族获得对氟硝基苯。被硫醇取代，随后被氧化。在标准下。使适应。NP 砜与多种芳烃之间的改良 Julia 反应。醛提供相应的苯乙烯、芪和肉桂酸酯衍生物。产率 ?97% 和良好的立体选择性。提出了机械原理来解释 obsd。结果。[在 SciFinder (R) 上]
• Prevention of Marine Biofouling Using the Natural Allelopathic Compound Batatasin-III and Synthetic Analogues
  作者：Lindon W. K. Moodie、Rozenn Trepos、Gunnar Cervin、Kari Anne Bråthen、Bente Lindgård、Rigmor Reiersen、Patrick Cahill、Henrik Pavia、Claire Hellio、Johan Svenson

  DOI：10.1021/acs.jnatprod.7b00129

  日期：2017.7.28

  The species of microalgae examined displayed a particular sensitivity toward the evaluated compounds at low ng/mL concentrations. It was shown that several of the natural and synthetic compounds exerted their repelling activities via nontoxic and reversible mechanisms. The activities of the most active compounds such as 3,5-dimethoxybibenzyl (5), 3,4-dimethoxybibenzyl (9), and 3-hydroxy-3′,4,5′-trimethoxybibenzyl

  本研究报告了对海洋环境中化感作用的陆地天然产物作为防污剂的首次综合评估。为了研究天然二氢二苯乙烯支架的防污潜力，制备了22种具有不同取代模式的合成二氢二苯乙烯类化合物的文库，并评估了它们的防污能力，其中许多取代型自然存在于陆生植物中。在针对16种污染海洋生物的广泛筛选中评估了这些化合物。研究表明，二氢二苯乙烯骨架对海洋微污垢和大型污垢均具有强大的一般防污效果，并在低浓度下具有抑制活性。在低ng / mL浓度下，所检查的微藻物种对所评估的化合物表现出特殊的敏感性。结果表明，几种天然和合成化合物均通过无毒和可逆的机制发挥其排斥作用。活性最高的化合物，例如3,5-二甲氧基联苄（5），3，4-二甲氧基联苄基（9）和3-羟基-3′，4，5′-三甲氧基联苄基（20）与用作防污助剂的商业防污剂Sea-n相当。陆地化感化天然产物对付海洋污染的研究代表了一种设计“绿色”防污技术的新颖策略，这些化合物为传统的杀生物防污剂提供了潜在的替代品。