(Z)-2,4-dichloro-1-(2-phenylethenyl)-benzene | 1657-69-8

• 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)-2,4-dichloro-1-(2-phenylethenyl)-benzene
• 英文别名: cis-2,4-Dichlorstilben
• CAS: 1657-69-8
• 化学式: C₁₄H₁₀Cl₂
• 分子量: 249.139
• InChiKey: JUXNFVMNPVWORX-SREVYHEPSA-N

物化性质

• 沸点：
  140-150 °C
• 密度：
  1.267±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.16
• 重原子数：
  16.0
• 可旋转键数：
  2.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  0.0
• 氢给体数：
  0.0
• 氢受体数：
  0.0

反应信息

• 作为反应物：
  描述：

  氯仿 、 (Z)-2,4-dichloro-1-(2-phenylethenyl)-benzene 在 sodium hydroxide 、 苄基三乙基氯化铵 作用下， 反应 48.0h， 生成
  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：

  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 (Z)-2,4-dichloro-1-(2-phenylethenyl)-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

• 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。