4-bromophenyl 2,3,5,6-tetrafluoro-4-(trifluoromethyl)phenyl ether | 97631-87-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 4-bromophenyl 2,3,5,6-tetrafluoro-4-(trifluoromethyl)phenyl ether
• 英文别名: 1-(4-Bromophenoxy)-2,3,5,6-tetrafluoro-4-(trifluoromethyl)benzene
• CAS: 97631-87-3
• 化学式: C₁₃H₄BrF₇O
• 分子量: 389.067
• InChiKey: QWNCCFYOUORWJP-UHFFFAOYSA-N

物化性质

• 沸点：
  265.2±40.0 °C(Predicted)
• 密度：
  1.717±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.4
• 重原子数：
  22
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.08
• 拓扑面积：
  9.2
• 氢给体数：
  0
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  4-bromophenyl 2,3,5,6-tetrafluoro-4-(trifluoromethyl)phenyl ether 在 盐酸 、 碘 、 sodium methylate 、 sodium hydride 、 magnesium 、 1,2-二溴乙烷 作用下， 以 乙醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 21.0h， 生成 他莫昔芬
  参考文献：
  名称：

  Jarman, Michael; McCague, Raymond, Journal of Chemical Research, Miniprint, 1985, # 4, p. 1342 - 1388

  摘要：

  DOI：
• 作为产物：
  描述：

  4-溴苯酚 、 八氟甲苯 在 sodium hydroxide 、 四丁基硫酸氢铵 作用下， 以 二氯甲烷 、 水 为溶剂， 反应 0.5h， 以100%的产率得到4-bromophenyl 2,3,5,6-tetrafluoro-4-(trifluoromethyl)phenyl ether
  参考文献：
  名称：

  Jarman, Michael; McCague, Raymond, Journal of Chemical Research, Miniprint, 1985, # 4, p. 1301 - 1341

  摘要：

  DOI：

文献信息

• Transition-Metal-Free Catalytic Hydrodefluorination of Polyfluoroarenes by Concerted Nucleophilic Aromatic Substitution with a Hydrosilicate
  作者：Kotaro Kikushima、Mary Grellier、Masato Ohashi、Sensuke Ogoshi

  DOI：10.1002/anie.201708003

  日期：2017.12.18

  A transition‐metal‐free catalytic hydrodefluorination (HDF) reaction of polyfluoroarenes is described. The reaction involves direct hydride transfer from a hydrosilicate as the key intermediate, which is generated from a hydrosilane and a fluoride salt. The eliminated fluoride regenerates the hydrosilicate to complete the catalytic cycle. Dispersion‐corrected DFT calculations indicated that the HDF

  描述了多氟芳烃的无过渡金属催化加氢脱氟（HDF）反应。该反应涉及从氢硅酸盐作为主要中间体的氢化物直接转移，这是由氢硅烷和氟化物盐生成的。除去的氟化物使氢硅酸盐再生，从而完成催化循环。分散校正的DFT计算表明HDF反应通过协调的亲核芳族取代（CS N Ar）过程进行。
• Nonisomerizable analogs of (Z)- and (E)-4-hydroxytamoxifen. Synthesis and endocrinological properties of substituted diphenylbenzocycloheptenes
  作者：Raymond McCague、Guy Leclercq、V. Craig Jordan

  DOI：10.1021/jm00402a005

  日期：1988.7

  corresponding derivatives of tamoxifen although in the MCF-7 assay 6 was slightly less effective than 4-hydroxytamoxifen at 10(-6) and 10(-7) M. The compound 8 analogues to cis-4-hydroxytamoxifen antagonized the growth stimulation by estradiol of MCF-7 cell or rat uterus growth, and it is therefore an antiestrogen, but its potency was somewhat less, both as an antiestrogen and an estrogen, than reported

  取代的8,9-二苯基-6,7-二氢-5H-苯并环庚烯6-8是（Z）-反-4-羟基他莫昔芬，（E）-顺他莫昔芬和（E）-顺式4-羟基他莫昔芬是由7-甲氧基-1-苯并亚砜合成的。通过共同的合成中间体分别制备羟基化合物6和8，从该中间体可以特异性地裂解全氟对甲苯基或甲基醚官能团。测定了化合物对细胞溶质和MCF-7全细胞中雌激素受体的结合亲和力，以及体外和体内大鼠子宫对MCF-7细胞的生长抑制作用。环状类似物5-7的内分泌学特性与他莫昔芬的相应衍生物的内分泌学特性相似，尽管在MCF-7分析中6在10（-6）和10（-7）M时比4-羟基他莫昔芬的有效性稍差。顺式-4-羟基他莫昔芬的化合物8类似物拮抗雌二醇对MCF-7细胞或大鼠子宫的生长刺激，因此它是抗雌激素药，但作为抗雌激素药和雌激素药，其效价均比报道的要低。顺式4-羟基他莫昔芬的作用是由于异构化为更有效的反式异构体而改变了后者的生化特性。奇怪的是
• Synthesis of Z-1,1-Dichloro-2-[4-(2-dimethylaminoethoxy)phenyl]-2-(4-hydroxyphenyl)-3-phenyl Cyclopropane and Z-1,1-Dichloro-2-[4-(2-dimethylaminoethoxy)phenyl]-2-(4-chlorophenyl)-3-phenyl Cyclopropane
  作者：Satendra Singh、Robert A. Magarian

  DOI：10.1246/cl.1994.1821

  日期：1994.10

  steps in the synthesis are the preparation of the pure Z-ethene, the stereospecific addition of dichlorocarbene, amino-dehalogenation and deprotection of the phenol. Heptafluorotolyl protecting group is used in the synthesis of pure Z-ethene which is stable under basic heterogenous cyclopropanation reaction conditions.

  描述了标题化合物的合成。合成的关键步骤是纯Z-乙烯的制备、二氯卡宾的立体定向加成、苯酚的氨基脱卤和脱保护。七氟甲苯基保护基团用于合成在碱性异相环丙烷化反应条件下稳定的纯 Z-乙烯。
• McCague, Raymond, Journal of Chemical Research, Miniprint, 1986, # 2, p. 771 - 793
  作者：McCague, Raymond

  DOI：——

  日期：——
• Influence of the Length and Positioning of the Antiestrogenic Side Chain of Endoxifen and 4-Hydroxytamoxifen on Gene Activation and Growth of Estrogen Receptor Positive Cancer Cells
  作者：Philipp Y. Maximov、Daphne J. Fernandes、Russell E. McDaniel、Cynthia B. Myers、Ramona F. Curpan、V. Craig Jordan

  DOI：10.1021/jm500569h

  日期：2014.6.12

  Tamoxifen has biologically active metabolites: 4-hydroxytamoxifen (4OHT) and endoxifen. The E-isomers are not stable in solution as Z-isomerization occurs. We have synthesized fixed ring (FR) analogues of 4OHT and endoxifen as well as FR E and Z isomers with methoxy and ethoxy side chains. Pharmacologic properties were documented in the MCF-7 cell line, and prolactin synthesis was assessed in GH3 rat pituitary tumor cells. The FR Z-isomers of 4OHT and endoxifen were equivalent to 4OHT and endoxifen. Other test compounds used possessed partial estrogenic activity. The E-isomers of FR 4OHT and endoxifen had no estrogenic activity at therapeutic serum concentrations. None of the newly synthesized compounds were able to down-regulate ER levels. Molecular modeling demonstrated that some compounds would each create a best fit with a novel agonist conformation of the ER The results demonstrate modulation by the ER complex of cell replication or gene transcription in cancer.