2,4-difluoro-3-(trimethylsilyl)anisole | 114636-02-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: 2,4-difluoro-3-(trimethylsilyl)anisole
• 英文别名: 1,3-Difluoro-4-methoxy-2-(trimethylsilyl)benzene；(2,6-difluoro-3-methoxyphenyl)-trimethylsilane
• CAS: 114636-02-1
• 化学式: C₁₀H₁₄F₂OSi
• 分子量: 216.303
• InChiKey: HFQBTBSSGJSKRE-UHFFFAOYSA-N

物化性质

• 沸点：
  212.3±40.0 °C(Predicted)
• 密度：
  1.04±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.52
• 重原子数：
  14
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  9.2
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2,4-difluoro-3-(trimethylsilyl)anisole 在 正丁基锂 、 2,2,2-三氟乙醇 、 四丁基氟化铵 作用下， 以 四氢呋喃 为溶剂， 反应 4.75h， 生成 3,5-二氟-2-甲氧基苯甲醛
  参考文献：
  名称：

  Syntheses of 2,5- and 2,6-difluoronorepinephrine, 2,5-difluoroepinephrine, and 2,6-difluorophenylephrine: effect of disubstitution with fluorine on adrenergic activity

  摘要：

  Synthetic routes to difluorinated analogs of the adrenergic agonists, norepinephrine (NE), epinephrine (E), and phenylephrine (PE) have been developed. The syntheses were based on elaboration of the ethanolamine side chains from the appropriately polyfunctionalized benzaldehydes, The benzaldehydes were prepared from precursor difluorinated benzenes by sequential regioselective lithiations and reaction with electrophiles to introduce hydroxyl and carboxaldehyde functionalities. Binding and functional assay data demonstrate that the 2,6-difluorinated analogs are relatively inactive at both alpha- and beta-adrenergic receptors. These results are consistent with earlier observations that 2-fluoro substitution of adrenergic agonists decreases alpha-adrenergic activity whereas 6-fluoro substitution decreases beta-adrenergic activity.

  DOI：

  10.1021/jm00076a024
• 作为产物：
  描述：

  2,4-二氟苯酚 在 正丁基锂 、 potassium carbonate 作用下， 以 丙酮 为溶剂， 反应 49.75h， 生成 2,4-difluoro-3-(trimethylsilyl)anisole
  参考文献：
  名称：

  Syntheses of 2,5- and 2,6-difluoronorepinephrine, 2,5-difluoroepinephrine, and 2,6-difluorophenylephrine: effect of disubstitution with fluorine on adrenergic activity

  摘要：

  Synthetic routes to difluorinated analogs of the adrenergic agonists, norepinephrine (NE), epinephrine (E), and phenylephrine (PE) have been developed. The syntheses were based on elaboration of the ethanolamine side chains from the appropriately polyfunctionalized benzaldehydes, The benzaldehydes were prepared from precursor difluorinated benzenes by sequential regioselective lithiations and reaction with electrophiles to introduce hydroxyl and carboxaldehyde functionalities. Binding and functional assay data demonstrate that the 2,6-difluorinated analogs are relatively inactive at both alpha- and beta-adrenergic receptors. These results are consistent with earlier observations that 2-fluoro substitution of adrenergic agonists decreases alpha-adrenergic activity whereas 6-fluoro substitution decreases beta-adrenergic activity.

  DOI：

  10.1021/jm00076a024

文献信息

• Synthesis and antibacterial activity of 3-benzylamide derivatives as FtsZ inhibitors
  作者：Zhongping Hu、Shasha Zhang、Weicheng Zhou、Xiang Ma、Guangya Xiang

  DOI：10.1016/j.bmcl.2017.02.032

  日期：2017.4

  series of PC190723 derivatives was synthesized and investigated for their antimicrobial activity. The compounds exhibited good activity against several Gram-positive bacteria as determined by comparison of diameters of the zone of inhibition of test compounds and standard antibiotics. Compound 9 with a fluorine substitution on the phenyl ring showed the best antibacterial activity in the series against

  人类病理细菌的多药耐药菌株的出现和传播正在对全世界的公共卫生构成威胁。在当前的研究中，合成了一系列PC190723衍生物并研究了其抗菌活性。通过比较测试化合物和标准抗生素的抑制区域的直径来确定，该化合物对几种革兰氏阳性细菌表现出良好的活性。在苯环上具有氟取代基的化合物9在该系列中对耻垢分枝杆菌具有0.62的区域比，对于金黄色葡萄球菌具有0.44的区域比显示出最佳的抗菌活性。这项研究的结果表明，基于独特的3-甲氧基苯甲酰胺药效基团，
• Deprotonative Silylation of Aromatic C–H Bonds Mediated by a Combination of Trifluoromethyltrialkylsilane and Fluoride
  作者：Kanako Nozawa-Kumada、Sayuri Osawa、Midori Sasaki、Isabelle Chataigner、Masanori Shigeno、Yoshinori Kondo

  DOI：10.1021/acs.joc.7b01525

  日期：2017.9.15

  method for the deprotonative silylation of aromatic C–H bonds has been developed using trifluoromethyltrimethylsilane (CF3SiMe3, Ruppert–Prakash reagent) and a catalytic amount of fluoride. In this reaction, CF3SiMe3 is considered to act as a base and a silicon electrophile. This process is highly tolerant to various functional groups on heteroarenes and benzenes. Furthermore, this method can be applied

  已经开发了一种使用三氟甲基三甲基硅烷（CF 3 SiMe 3，Ruppert-Prakash试剂）和催化量氟化物的芳香族C-H键去质子化甲硅烷基化的方法。在该反应中，认为CF 3 SiMe 3用作碱和亲电子硅。该过程高度耐受杂芳烃和苯上的各种官能团。此外，该方法可以应用于TAC-101的含三甲基甲硅烷基的类似物的合成，TAC-101是对视黄酸受体α（RAR-α）结合具有选择性亲和力的生物活性合成类视黄醇。我们还报告了甲硅烷基化产物进一步转变为有用的衍生物的过程。
• 吡啶(或苯)并噻唑化合物及其中间体、制备方 法和应用
  申请人：上海医药工业研究院

  公开号：CN103724360B

  公开（公告）日：2016-08-10

  本发明公开了一种如式A所示的吡啶(或苯)并噻唑化合物及其中间体、制备方法和应用。其中，Z为N或CH，X为O或NH，R1为H、C1‑3的烷基或C1‑3的烷氧基，R2和R4独立的为H、F或Cl，R3为H、F、COR5或SO2NH2，R5为OH、C1‑3的烷氧基或NR6R7，NR6R7为NHCH3、NHC2H5、N(CH3)2或如式L所示的取代基，R8、R9、R10和R11各自独立的为H、C1‑3的烷基或卤素。本发明还公开了含如式A所示的化合物的药物组合物及其在制备治疗细菌感染性疾病的药物中的应用。本发明中所述的如式A所示的化合物具有良好的抗菌活性，对新抗菌药物的开发具有重要意义。
• Unexpected regioselectivity in the lithiation of fluoroanisoles
  作者：David C. Furlano、Silvia N. Calderon、George Chen、Kenneth L. Kirk

  DOI：10.1021/jo00249a004

  日期：1988.7
• FURLANO, DAVID C.;CALDERON, SILVIA N.;CHEN, GEORGE;KIRK, KENNETH L., J. ORG. CHEM., 53,(1988) N 14, 3145-3147
  作者：FURLANO, DAVID C.、CALDERON, SILVIA N.、CHEN, GEORGE、KIRK, KENNETH L.

  DOI：——

  日期：——