(Z)-1-fluoro-4-(4-methoxystyryl)benzene | 64583-10-4

• 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-fluoro-4-(4-methoxystyryl)benzene
• 英文别名: Trans-1-fluoro-4-(4-methoxystyryl)benzene (10)；1-fluoro-4-[(Z)-2-(4-methoxyphenyl)ethenyl]benzene
• CAS: 64583-10-4
• 化学式: C₁₅H₁₃FO
• 分子量: 228.266
• InChiKey: RWZRJLFTAMZFCM-IHWYPQMZSA-N

物化性质

• 沸点：
  340.4±11.0 °C(Predicted)
• 密度：
  1.136±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.3
• 重原子数：
  17
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  9.2
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (Z)-1-fluoro-4-(4-methoxystyryl)benzene 在 pyridinium hydrobromide perbromide 作用下， 生成 1-[(1R,2S)-1,2-dibromo-2-(4-fluorophenyl)ethyl]-4-methoxybenzene
  参考文献：
  名称：

  Gascoyne,J.M. et al., Journal of the Chemical Society. Perkin transactions II, 1977, p. 1051 - 1057

  摘要：

  DOI：
• 作为产物：
  描述：

  对甲氧基苯乙酸 在 喹啉 、 chromium(III) oxide 、 乙酸酐 、 三乙胺 、 copper(II) oxide 作用下， 反应 2.0h， 生成 (Z)-1-fluoro-4-(4-methoxystyryl)benzene
  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

文献信息

• Highly selective catalytic trans-hydroboration of alkynes mediated by borenium cations and B(C₆F₅)₃
  作者：John S. McGough、Samuel M. Butler、Ian A. Cade、Michael J. Ingleson

  DOI：10.1039/c5sc04798f

  日期：——

  The trans-hydroboration of terminal alkynes mediated by borenium cations [NHC(9-BBN)]+ (NHC = N-heterocyclic carbene, 9-BBN = 9-borabicyclo(3.3.1)nonane) exclusively affords Z-vinylboranes. NHCs and chelating dialkyl substituents on the borenium cation and...

  由硼鎓阳离子 [NHC(9-BBN)]+ (NHC = N-杂环卡宾，9-BBN = 9-硼二环(3.3.1)壬烷) 介导的末端炔烃的反式硼氢化反应专门提供 Z-乙烯基硼烷。NHCs和硼鎓阳离子上的螯合二烷基取代基和...
• One-Pot Intermolecular Reductive Cross-Coupling of Deactivated Aldehydes to Unsymmetrically 1,2-Disubstituted Alkenes
  作者：Anna I. Arkhypchuk、Nicolas D’Imperio、Sascha Ott

  DOI：10.1021/acs.orglett.8b01754

  日期：2018.9.7

  MesP(Li)TMS, and an aldehyde affords Mes-phosphaalkenes which, upon methanol addition and P-oxidation, react with a second carbonyl compound site specifically to produce unsymmetric alkenes. The E/Z selectivity of the one-pot cross coupling is largely determined by the electronic nature of the aryl substituent of the first aldehyde, with electron-donating groups giving rise to increased amounts of Z-alkenes.

  锂化的仲膦MesP（Li）TMS与醛之间的磷酸-彼得森反应提供了Mes-磷烯烃，在甲醇加成和P-氧化后，Mes-磷烯烃与第二个羰基化合物位点专门反应生成不对称烯烃。一锅交叉偶联的E / Z选择性在很大程度上取决于第一醛的芳基取代基的电子性质，给电子基团导致Z-烯烃的量增加。
• Heck Couplings at Room Temperature in Nanometer Aqueous Micelles
  作者：Bruce H. Lipshutz、Benjamin R. Taft

  DOI：10.1021/ol702755g

  日期：2008.4.1

  or the vitamin E-based PTS, both of which form nanomicelles in water, promotes Heck cross-couplings of non-water-soluble partners at ambient temperatures. These are the first examples of Heck reactions conducted in water (as the only solvent) at room temperature.

  非离子两亲物（例如Triton X-100或基于维生素E的PTS）在水中均会形成纳米胶束，在环境温度下会促进非水溶性伴侣的Heck交叉偶联。这些是室温下在水（作为唯一的溶剂）中进行的Heck反应的第一个例子。
• Synthesis and tyrosinase inhibition activity of trans -stilbene derivatives
  作者：Tabasum Ismail、Syed Shafi、Jada Srinivas、Dhiman Sarkar、Yasrib Qurishi、Jabeena Khazir、Mohammad Sarwar Alam、Halmuthur Mahabalarao Sampath Kumar

  DOI：10.1016/j.bioorg.2016.01.001

  日期：2016.2

  focussed library of trans-stilbene compounds through Wittig and other base catalysed condensation reactions is presented. The synthesized stilbenes were screened for their inhibitory potential against murine tyrosinase activity to explore the structure activity relationship (SAR). Presence of electron withdrawing group (-CN) at the double bond and hydroxyl group or halogen atom especially at para-position

  介绍了通过Wittig和其他碱催化的缩合反应合成反式二苯乙烯化合物的聚焦库。筛选合成的对苯二酚对鼠酪氨酸酶活性的抑制潜力，以探讨其结构活性关系（SAR）。发现在双键和羟基或卤素原子上，特别是在芳环对位上的吸电子基团（-CN）显着提高了抑制活性。在所有筛选的化合物中，发现化合物2、6、8、10、11、15和21表现出明显的抑制活性。发现化合物21（（E）-2,3-双（4-羟基苯基）丙烯腈）最具活性，IC50值为5.06μM，小于值10的一半。在相似条件下观察到白藜芦醇（鼠酪氨酸酶活性研究中使用的通用标准）为78μM。从本研究中获得的结果揭示了结构/官能团对类胡萝卜素部分的酪氨酸酶抑制活性的敏感性，并有望对新型，选择性和有效的酪氨酸酶抑制剂的设计和合成非常有帮助。
• Photoinduced NiH Catalysis with Trialkylamines for the Stereodivergent Transfer Semi‐Hydrogenation of Alkynes
  作者：Tingjun Hu、Mohammad Jaber、Gaël Tran、Didier Bouyssi、Nuno Monteiro、Abderrahmane Amgoune

  DOI：10.1002/chem.202301636

  日期：2023.10.23

  Dual nickel and photoredox catalysis enables the semi-reduction of internal aryl alkynes in the presence of a trialkylamine acting both as a reductive quencher and as a transfer hydrogenation reagent. The E/Z-stereoselectivity can be controlled with the aid of an alcohol additive.

  双镍和光氧化还原催化能够在三烷基胺存在下实现内部芳基炔的半还原，三烷基胺既充当还原猝灭剂又充当转移氢化试剂。E/Z-立体选择性可以借助醇添加剂来控制。