(Z)-1,2,3-trimethoxy-5-styrylbenzene | 74809-44-2

• 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: (Z)-1,2,3-trimethoxy-5-styrylbenzene
• 英文别名: (Z)-3,4,5-trimethoxystilbene；1,2,3-trimethoxy-5-styrylbenzene；(Z)-3′,4′,5′-trimethoxystilbene；(Z)3,5-Trimethoxystilbene；1,2,3-trimethoxy-5-[(Z)-2-phenylethenyl]benzene
• CAS: 74809-44-2
• 化学式: C₁₇H₁₈O₃
• 分子量: 270.328
• InChiKey: CMQGCWMEXQRWSS-KTKRTIGZSA-N

物化性质

• 沸点：
  398.8±37.0 °C(Predicted)
• 密度：
  1.104±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.1
• 重原子数：
  20
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  27.7
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  氯仿 、 (Z)-1,2,3-trimethoxy-5-styrylbenzene 在 sodium hydroxide 、 苄基三乙基氯化铵 作用下， 反应 48.0h， 以36%的产率得到Z-1,1-dichloro-2-(3,4,5-trimethoxyphenyl)-3-phenylcyclopropane
  参考文献：
  名称：

  Synthesis and biological evaluation of 1,1-Dichloro-2,3-diarylcyclopropanes as antitubulin and anti-breast cancer agents

  摘要：

  Z-1,1-Dichloro-2,3-diphenylcyclopropane (1) is an effective 'anti-breast cancer agent in rodents and in cell culture. We recently determined that 1 inhibits tubulin assembly in vitro. and causes microtubule loss in breast cancer cells, leading to accumulation in the G2/M portion of the cell cycle. Aryl ring-halogenated, methoxylated and benzyloxylated derivatives of 1, as well as its E-isomer and the dichlorocyclopropyl derivative of diethylstilbestrol (DES), were synthesized and tested for their ability to inhibit the assembly of tubulin into micro tubules. Including 1, 17 cyclopropyl compounds were tested. One (Z-1,1-dichloro-2-(4-methoxyphenyl)-3-phenylcyclopropane (12)) was found to be more active than 1. In addition, E-1,1-dichlorocyclopropylDES (17) was more potent than DES. The E-isomer of 1 (16) was inactive. The cytostatic activities of the compounds against MCF-7 and MDA-MB231 human breast cancer cells, and their abilities to perturb microtubules in MCF-7 cells were also evaluated. Z-Dichloro-2-(4-fluorophenyl)-3-phenylcyclo (5), Z-1,1-dichloro-2-(4-fluorophenyl)-3-(4-methoxyphenyl)cyclopropane (11), and Z-1,1-dichloro-2-(4-methoxyphenyl) -3-phenylcyclopropane (12) were more potent than 1 against the breast cancer cells. (C) 1997 Elsevier Science Ltd.

  DOI：

  10.1016/s0968-0896(97)00014-x
• 作为产物：
  描述：

  1,2,3-trimethoxy-5-(phenylethynyl)benzene 在 titanium(IV) isopropylate 、 正丁基锂 、 水 作用下， 以 四氢呋喃 为溶剂， 以90%的产率得到(Z)-1,2,3-trimethoxy-5-styrylbenzene
  参考文献：
  名称：

  A new synthesis of combretastatins A-4 and AVE-8062A

  摘要：

  Combretastatins A-4 and AVE-8062A have been synthesized by coupling 3,4,5-trimethoxyphenylacetylene with the corresponding iodomethoxyphenol and bromomethoxyaniline, followed by hydrolysis of the thermally-stable Ti(II)-alkyne complexes. (c) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2007.07.151

文献信息

• Energy-Transfer-Mediated Photocatalysis by a Bioinspired Organic Perylenephotosensitizer HiBRCP
  作者：Yan Zhang、Mingze Xia、Min Li、Qian Ping、Zhenbo Yuan、Xuanzhong Liu、Huimin Yin、Shuping Huang、Yijian Rao

  DOI：10.1021/acs.joc.1c01876

  日期：2021.11.5

  triplet energy was greatly improved, and then, it could markedly promote the efficient geometrical isomerization of alkenes from the E-isomer to the Z-isomer. Moreover, it was also effective for energy-transfer-mediated organometallic catalysis, which allowed realization of the cross-coupling of aryl bromides and carboxylic acids through efficient energy transfer from HiBRCP to nickel complexes. Thus, the

  能量转移在光催化中起着特殊的作用，它通过间接激发利用激发态的势能，其中光敏剂决定了反应的热力学可行性。受天然产物尾孢菌素的能量转移能力的启发，我们通过对尾孢菌素的结构修饰，开发了一种绿色高效的有机光敏剂 HiBRCP（六异丁酰还原尾孢菌素）。经过结构操作后，其三重态能量大大提高，从而显着促进烯烃从E-异构体到Z-异构体的高效几何异构化。-异构体。此外，它对能量转移介导的有机金属催化也很有效，通过从 HiBRCP 到镍配合物的有效能量转移，可以实现芳基溴化物和羧酸的交叉偶联。因此，对结构操纵与其光物理性质之间关系的研究为尾孢菌素的进一步修饰提供了指导，可应用于更有意义和更具挑战性的能量转移反应。
• Iron-Catalyzed Cross-Coupling of Bis-(aryl)manganese Nucleophiles with Alkenyl Halides: Optimization and Mechanistic Investigations
  作者：Lidie Rousseau、Alexandre Desaintjean、Paul Knochel、Guillaume Lefèvre

  DOI：10.3390/molecules25030723

  日期：——

  Various substituted bis-(aryl)manganese species were prepared from aryl bromides by one-pot insertion of magnesium turnings in the presence of LiCl and in situ trans-metalation with MnCl2 in THF at −5 °C within 2 h. These bis-(aryl)manganese reagents undergo smooth iron-catalyzed cross-couplings using 10 mol% Fe(acac)3 with various functionalized alkenyl iodides and bromides in 1 h at 25 °C. The aryl-alkenyl

  在 LiCl 存在下，通过一锅法插入镁屑，并在-5°C 下在 THF 中与 MnCl2 在 2 小时内原位金属转移，从芳基溴化物制备了各种取代的双（芳基）锰物种。这些双（芳基）锰试剂使用 10 mol% Fe(acac)3 与各种功能化的链烯基碘化物和溴化物在 25°C 下在 1 小时内进行平滑的铁催化交叉偶联。通过顺磁性 1 H-NMR 彻底研究了芳基-烯基交叉偶联反应机理，确定了三配位的 ate-铁 (II) 物种在催化过程中的关键作用。
• <i>Trans</i> Stereoselectivity in the Reaction of Cyclic Phosphonium Salts with Aromatic Aldehydes
  作者：Nicholas J. Lawrence、Hayrettin Beynek

  DOI：10.1055/s-1998-1702

  日期：1998.5

  The Wittig olefination of substituted aromatic aldehydes with ylides from phosphorinanium salts [RCH2P(Ph)(CH2)5]+Br- in which the phosphorus atom is incorporated into a six-membered ring, is E-selective.

  在磷鎓盐[RCH2P(Ph)(CH2)5]+Br-中，磷原子被纳入一个六元环内，以此类雌鎓与取代芳香醛进行Wittig烯化反应时，选择性地生成E型烯烃。
• (<i>Z</i>)-Selective Hydrosilylation of Terminal Alkynes with HSiMe(OSiMe₃)₂ Catalyzed by a Ruthenium Complex Containing an N-Heterocyclic Carbene
  作者：Yuichiro Mutoh、Yusei Mohara、Shinichi Saito

  DOI：10.1021/acs.orglett.7b02477

  日期：2017.10.6

  The N-heterocyclic-carbene-ligated ruthenium complex [RuHCl(CO)(H2IMes)(PCy3)] exhibits high catalytic activity for the (Z)-selective hydrosilylation of various terminal alkynes with 1,1,1,3,5,5,5-heptamethyltrisiloxane (HSiMe(OSiMe3)2). The stereoretentive derivatization of the (Z)-alkenylsiloxanes allows the synthesis of biologically active compounds, e.g. potent antitumor agents and inhibitors for

  所述N-杂环-碳烯-连接的钌络合物[RuHCl（CO）（H 2个IMES）（PCY 3）]显示出对（高催化活性Ž）与1,1,1,3-各种末端炔烃的氢化硅烷化-选择性， 5,5,5-七甲基三硅氧烷（HSiMe（OSiMe 3）2）。（Z）-烯基硅氧烷的立体保持衍生化允许合成生物活性化合物，例如有效的抗肿瘤剂和诱导型NO合酶的抑制剂。
• ANTI-INVASIVE COMPOUNDS
  申请人：Universiteit Gent

  公开号：US20150011620A1

  公开（公告）日：2015-01-08

  The present invention relates to the field of anti-invasive compounds and methods for predicting the anti-invasive activity of said compounds, as well as their use in the prevention and/or treatment of diseases associated with undesired cell invasion; in particular, this invention relates to the field of anti-invasive chalcone-like compounds.

  本发明涉及抗侵袭化合物领域，以及预测该类化合物抗侵袭活性的方法，以及它们在预防和/或治疗与不受欢迎的细胞侵袭相关的疾病中的用途；特别是，本发明涉及抗侵袭的类似香豆素化合物领域。