(E)-2,4-dichloro-1-styrylbenzene | 1657-47-2

• 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: (E)-2,4-dichloro-1-styrylbenzene
• 英文别名: 2,4-dichloro-stilbene；2,4-Dichlor-stilben；(E)-2,4-dichloro-1-(2-phenylethenyl)-benzene；2,4-Dichlor-trans-Stilben；trans-2,4-Dichlorstilben；2,4-dichloro-1-[(E)-2-phenylethenyl]benzene
• CAS: 1657-47-2
• 化学式: C₁₄H₁₀Cl₂
• 分子量: 249.139
• InChiKey: JUXNFVMNPVWORX-VOTSOKGWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.3
• 重原子数：
  16
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  0
• 氢给体数：
  0
• 氢受体数：
  0

反应信息

• 作为反应物：
  描述：

  (E)-2,4-dichloro-1-styrylbenzene 在 氯化亚砜 作用下， 生成
  参考文献：
  名称：

  FR1509479

  摘要：

  公开号：
• 作为产物：
  描述：

  2,4-二氯苯甲醛 在 喹啉 、 chromium(III) oxide 、 乙酸酐 、 三乙胺 、 copper(II) oxide 作用下， 反应 2.0h， 生成 (E)-2,4-dichloro-1-styrylbenzene
  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

• Tetraethylammonium iodide catalyzed synthesis of diaryl ketones via the merger of cleavage of C–C double bonds and recombination of aromatic groups
  作者：Xianghua Zeng、Daqian Xu、Chengxia Miao、Chungu Xia、Wei Sun

  DOI：10.1039/c4ra08764j

  日期：——

  An efficient method for synthesizing diaryl ketones via merging of oxidative cleavage of C–C double bonds and recombination of aromatic groups is developed with Et4NI (2.5 mol%) as the catalyst and NaIO4 as the oxidant. The control experiments provide valuable mechanistic insights into the formation of diaryl ketones, and suggest that NaIO4 serves as an epoxidation and nucleophilic deformylation reagent

  以Et 4 NI（2.5 mol％）为催化剂，NaIO 4为氧化剂，开发了一种有效的方法，该方法通过合并C–C双键的氧化裂解和芳族基团的重组来合成二芳基酮。对照实验为二芳基酮的形成提供了有价值的机理见解，并表明NaIO 4可作为环氧化和亲核去甲酰基化试剂。
• Facile and highly chemoselective synthesis of benzil derivatives via oxidation of stilbenes in an I2–H2O system
  作者：Xianghua Zeng、Chengxia Miao、Shoufeng Wang、Chungu Xia、Wei Sun

  DOI：10.1039/c3ra41489b

  日期：——

  A facile and highly chemoselective protocol for the synthesis of benzil derivatives has been developed by oxidation of stilbenes in an I2–H2O system under air. Notably, the method was applicable to 26 examples and provided up to 98% yield, avoiding the use of acid, metal catalysts and so on.

  通过在空气中的I 2 -H 2 O系统中对苯乙烯进行氧化，已经开发出一种易于合成且具有高度化学选择性的苯甲酰衍生物的方案。值得注意的是，该方法适用于26个实例，并且提供了高达98％的收率，避免了使用酸，金属催化剂等。
• <i>o</i>-Iodoxybenzoic acid mediated generation of aryl free radicals: synthesis of stilbenes through C–C cross-coupling with β-nitrostyrenes
  作者：Ganesh Wagh、Snehalata Autade、Pravin C. Patil、Krishnacharya G. Akamanchi

  DOI：10.1039/c7nj04701k

  日期：——

  substrate scope and transition metal free, mild reaction conditions, under an open atmosphere in a short reaction time. A free radical mediated mechanism was postulated and supported by radical trapping experiments. Application of the developed methodology is demonstrated through a simple, two step synthesis of resveratrol, a valuable stilbenoid for anticancer and neurological studies via its prodrug E-1,

  在硝基苯乙烯存在下，通过芳基肼和邻碘氧苯甲酸的组合生成芳基自由基导致了斯蒂苯类的合成，其方法是在随后消除亚硝酰基基团后形成新的碳-碳键。以高收率合成了具有优异E选择性的对称和不对称对苯二甲酸酯，具有宽的底物范围和无过渡金属，温和的反应条件，在开放的气氛中，较短的反应时间内的优势。自由基介导的机制是由自由基诱捕实验推测和支持的。通过简单的两步合成白藜芦醇（一种对抗癌和神经系统研究有用的有价值的类芪），证明了所开发方法的应用通过其前药E -1,3-二甲氧基-5-（4-甲氧基苯乙烯基）苯。
• Electrochemical Proton Reduction over Nickel Foam for <i>Z</i> ‐Stereoselective Semihydrogenation/deuteration of Functionalized Alkynes
  作者：Alejandro Valiente、Pablo Martínez‐Pardo、Gurpreet Kaur、Magnus J. Johansson、Belén Martín‐Matute

  DOI：10.1002/cssc.202102221

  日期：2022.1.10

  Foam catalyst: Commercially available nickel foam is an excellent catalyst for the electrochemical semihydrogenation/semideuteration of functionalized alkynes in diluted sulfuric acid under ambient conditions. Here, the applicability of this catalyst for the stereoselective synthesis of Z-alkenes and Z-alkenes-d2 is presented. The nickel foam is recyclable up to 14 times without losing its catalytic

  泡沫催化剂：市售的泡沫镍是在环境条件下稀硫酸中功能化炔烃的电化学半氢化/半氘化的优良催化剂。本文介绍了该催化剂在立体选择性合成Z-烯烃和Z-烯烃-d 2中的适用性。泡沫镍可回收多达 14 次，而不会失去其催化性能。
• TRIARYLAMINE DERIVATIVE AND ELECTROPHOTOGRAPHIC PHOTOSENSITIVE MEMBER
  申请人：KYOCERA Document Solutions Inc.

  公开号：US20160152552A1

  公开（公告）日：2016-06-02

  A triarylamine derivative is represented by general formula (1) shown below. In general formula (1), R 1 , R 2 , and R 3 each represent, independently of one another, a halogen atom, an optionally substituted alkyl group having a carbon number of at least 1 and no greater than 6, an optionally substituted alkoxy group having a carbon number of at least 1 and no greater than 6, or an optionally substituted aryl group having a carbon number of at least 6 and no greater than 12. In general formula (1), o, p, and q each represent, independently of one another, an integer of at least 0 and no greater than 4, and m and n each represent, independently of one another, an integer of at least 1 and no greater than 2.

  一个三芳胺衍生物由下面显示的一般式（1）表示。在一般式（1）中，R1、R2和R3分别表示独立的卤原子，具有至少1个碳原子且不大于6的可选择取代的烷基基团，具有至少1个碳原子且不大于6的可选择取代的烷氧基团，或具有至少6个碳原子且不大于12的可选择取代的芳基团。在一般式（1）中，o、p和q分别表示独立的至少为0且不大于4的整数，m和n分别表示独立的至少为1且不大于2的整数。