(Z)-4,4'-(1-phenylbut-1-ene-1,2-diyl)bis(methoxybenzene) | 13867-30-6

• 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)-4,4'-(1-phenylbut-1-ene-1,2-diyl)bis(methoxybenzene)
• 英文别名: Z-4,4'-(1-phenylbut-1-ene-1,2-diyl)bis(methoxybenzene)；(Z)-1,2-di-(4-methoxyphenyl)-1-phenyl-1-butene；1-methoxy-4-[(Z)-1-(4-methoxyphenyl)-1-phenylbut-1-en-2-yl]benzene
• CAS: 13867-30-6
• 化学式: C₂₄H₂₄O₂
• 分子量: 344.453
• InChiKey: UNGMCXLSGYYOBB-VHXPQNKSSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.1
• 重原子数：
  26
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.17
• 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：

  (Z)-4,4'-(1-phenylbut-1-ene-1,2-diyl)bis(methoxybenzene) 在 三溴化硼 作用下， 以 二氯甲烷 为溶剂， 反应 96.0h， 以78 mg的产率得到Z-4-(1-(4-hydroxyphenyl)-1-phenylbut-1-en-2-yl)phenol
  参考文献：
  名称：

  Structure−Function Relationships of Estrogenic Triphenylethylenes Related to Endoxifen and 4-Hydroxytamoxifen

  摘要：

  Estrogens can potentially be classified into planar (class I) or nonplanar (class II) categories, which might have biological consequences. 1,1,2-Triphenylethylene (TPE) derivatives were synthesized and evaluated against 17 beta-estradiol (E2) for their estrogenic activity in MCF-7 human breast cancer cells. All TPEs were estrogenic and, unlike 4-hydroxytamoxifen (4OHTAM) and Endoxifen, induced cell growth to a level comparable to that of E2. All the TPEs increased ERE activity in MCF-7:WS8 cells with the order of potency as followed: E2 > 1,1-bis(4,4'-hydroxyphenyl)-2-phenylbut-1-ene (15) > 1,1,2-tris(4-hydroxyphenyl)but-1-ene (3) > Z 4-(1-(4-hydroxyphenyl)-1-phenylbut-1-en-2-yl)phenol (7) > E 4-(1-(4-hydroxyphenyl)-1-phenylbut-1-en-2-yl)phenol (6) > Z(4-(1-(4-ethoxyphenyl)-1-(4-hydroxyphenyl)but-1-en-2-yl)phenol (12) > 4-OHTAM. Transient transfection of the ER-negative breast cancer cell line T47D:C4:2 with wild-type ER or D351G ER mutant revealed that all of the TPEs increased ERE activity in the cells expressing the wild-type ER but not the mutant, thus confirming the importance of Asp351 for ER activation by the TPEs. The findings confirm E2 as a class I estrogen and the TPEs as class II estrogens. Using available conformations of the ER liganded with 4OHTAM or diethylstilbestrol, the TPEs optimally occupy the 4OHTAM ER conformation that expresses Asp351.

  DOI：

  10.1021/jm901907u
• 作为产物：
  描述：

  1,2-bis-(4-methoxy-phenyl)-1-phenyl-butan-1-ol 在 磷酸 、 水 作用下， 以 四氢呋喃 为溶剂， 反应 2.0h， 以0.322 g的产率得到(E)-4,4'-(1-phenylbut-1-ene-1,2-diyl)bis(methoxybenzene)
  参考文献：
  名称：

  Structure−Function Relationships of Estrogenic Triphenylethylenes Related to Endoxifen and 4-Hydroxytamoxifen

  摘要：

  Estrogens can potentially be classified into planar (class I) or nonplanar (class II) categories, which might have biological consequences. 1,1,2-Triphenylethylene (TPE) derivatives were synthesized and evaluated against 17 beta-estradiol (E2) for their estrogenic activity in MCF-7 human breast cancer cells. All TPEs were estrogenic and, unlike 4-hydroxytamoxifen (4OHTAM) and Endoxifen, induced cell growth to a level comparable to that of E2. All the TPEs increased ERE activity in MCF-7:WS8 cells with the order of potency as followed: E2 > 1,1-bis(4,4'-hydroxyphenyl)-2-phenylbut-1-ene (15) > 1,1,2-tris(4-hydroxyphenyl)but-1-ene (3) > Z 4-(1-(4-hydroxyphenyl)-1-phenylbut-1-en-2-yl)phenol (7) > E 4-(1-(4-hydroxyphenyl)-1-phenylbut-1-en-2-yl)phenol (6) > Z(4-(1-(4-ethoxyphenyl)-1-(4-hydroxyphenyl)but-1-en-2-yl)phenol (12) > 4-OHTAM. Transient transfection of the ER-negative breast cancer cell line T47D:C4:2 with wild-type ER or D351G ER mutant revealed that all of the TPEs increased ERE activity in the cells expressing the wild-type ER but not the mutant, thus confirming the importance of Asp351 for ER activation by the TPEs. The findings confirm E2 as a class I estrogen and the TPEs as class II estrogens. Using available conformations of the ER liganded with 4OHTAM or diethylstilbestrol, the TPEs optimally occupy the 4OHTAM ER conformation that expresses Asp351.

  DOI：

  10.1021/jm901907u

文献信息

• Tetrasubstituted Olefin Synthesis via Pd-Catalyzed Addition of Arylboronic Acids to Internal Alkynes Using O₂ as an Oxidant
  作者：Chengxiang Zhou、Richard C. Larock

  DOI：10.1021/jo060104d

  日期：2006.4.1

  alkynes provides a convenient route to a wide variety of tetrasubstituted olefins. The reaction is conducted in DMSO using molecular O2 as an oxidant in the absence of any base. The reaction involves the cis addition of two aryl groups from the arylboronic acid to opposite ends of the triple bond of the internal alkyne. The synthesis tolerates a wide variety of functional groups, including alcohol, aldehyde

  芳基硼酸和内部炔烃的Pd（II）催化反应为广泛的四取代烯烃提供了便捷的途径。该反应在不存在任何碱的情况下使用分子O 2作为氧化剂在DMSO中进行。该反应涉及从芳基硼酸顺式加成两个芳基至内部炔的三键的相对端。该合成可耐受多种官能团，包括醇，醛，酯，TMS和乙缩醛基团。富电子的二烷基乙炔（例如4-辛炔）以中等收率提供高度取代的1,3-二烯。通过芳基硼酸的均偶联，非常温和的O 2 / DMSO条件也提供了良好的佳收率的联芳基。
• Microwave-assisted one-pot diboration/Suzuki cross-couplings. A rapid route to tetrasubstituted alkenes
  作者：Hana Prokopcová、Jesús Ramírez、Elena Fernández、C. Oliver Kappe

  DOI：10.1016/j.tetlet.2008.06.017

  日期：2008.8

  terminal alkynes undergo rapid platinum(0)-catalyzed diboration with bis(pinacolato)diboron in dioxane to yield cis-1,2-bis(boryl)alkenes under sealed vessel microwave conditions. Subsequent addition of aryl bromides, base and a palladium catalyst to the reaction vial followed by resubjection to microwave conditions provides tetrasubstituted ethylenes in high yields via Suzuki cross-coupling of the boron

  内部和末端炔烃在二恶烷中用双（频哪醇）二硼进行铂（0）催化的快速硼氢化反应，在密封容器微波条件下生成顺式-1,2-双（硼基）烯烃。随后将芳基溴化物，碱和钯催化剂加至反应瓶中，然后再置于微波条件下，通过硼中间体的铃木（Suzuki）交叉偶联以高收率提供四取代的乙烯。
• SCHNEIDER, M. R.;ANGERER, E. VON;SCHOENENBERGER, H.;MICHEL, R. TH.;FORTME+, J. MED. CHEM., 1982, 25, N 9, 1070-1077
  作者：SCHNEIDER, M. R.、ANGERER, E. VON、SCHOENENBERGER, H.、MICHEL, R. TH.、FORTME+

  DOI：——

  日期：——
• Structure−Function Relationships of Estrogenic Triphenylethylenes Related to Endoxifen and 4-Hydroxytamoxifen
  作者：Philipp Y. Maximov、Cynthia B. Myers、Ramona F. Curpan、Joan S. Lewis-Wambi、V. Craig Jordan

  DOI：10.1021/jm901907u

  日期：2010.4.22

  Estrogens can potentially be classified into planar (class I) or nonplanar (class II) categories, which might have biological consequences. 1,1,2-Triphenylethylene (TPE) derivatives were synthesized and evaluated against 17 beta-estradiol (E2) for their estrogenic activity in MCF-7 human breast cancer cells. All TPEs were estrogenic and, unlike 4-hydroxytamoxifen (4OHTAM) and Endoxifen, induced cell growth to a level comparable to that of E2. All the TPEs increased ERE activity in MCF-7:WS8 cells with the order of potency as followed: E2 > 1,1-bis(4,4'-hydroxyphenyl)-2-phenylbut-1-ene (15) > 1,1,2-tris(4-hydroxyphenyl)but-1-ene (3) > Z 4-(1-(4-hydroxyphenyl)-1-phenylbut-1-en-2-yl)phenol (7) > E 4-(1-(4-hydroxyphenyl)-1-phenylbut-1-en-2-yl)phenol (6) > Z(4-(1-(4-ethoxyphenyl)-1-(4-hydroxyphenyl)but-1-en-2-yl)phenol (12) > 4-OHTAM. Transient transfection of the ER-negative breast cancer cell line T47D:C4:2 with wild-type ER or D351G ER mutant revealed that all of the TPEs increased ERE activity in the cells expressing the wild-type ER but not the mutant, thus confirming the importance of Asp351 for ER activation by the TPEs. The findings confirm E2 as a class I estrogen and the TPEs as class II estrogens. Using available conformations of the ER liganded with 4OHTAM or diethylstilbestrol, the TPEs optimally occupy the 4OHTAM ER conformation that expresses Asp351.