(4-fluorophenyl)-(thiophen-2-yl)-methanol | 151917-31-6

• 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-fluorophenyl)-(thiophen-2-yl)-methanol
• 英文别名: (4-fluorophenyl)-(thien-2-yl)methanol；(4-fluorophenyl)-thiophen-2-ylmethanol
• CAS: 151917-31-6
• 化学式: C₁₁H₉FOS
• 分子量: 208.256
• InChiKey: KAOUGVSQPMIGST-UHFFFAOYSA-N

物化性质

• 沸点：
  331.7±32.0 °C(Predicted)
• 密度：
  1.295±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  14
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.09
• 拓扑面积：
  48.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (4-fluorophenyl)-(thiophen-2-yl)-methanol 在 氯化亚砜 作用下， 以 苯 为溶剂， 反应 1.0h， 生成 (4-fluorophenyl)(thien-2-yl)methyl chloride
  参考文献：
  名称：

  多巴胺转运蛋白（DAT）的有效和选择性配体：新型4- [2-（2-（二苯基甲氧基）乙基] -1-（3-苯基丙基）哌啶类似物的结构-活性关系研究。

  摘要：

  多巴胺转运蛋白（DAT）特异性配体4- [2-（二苯基甲氧基）乙基] -1-（3-苯基丙基）哌啶（1a）的分子结构修饰产生了几种新的类似物。在大鼠纹状体膜中评估了这些新分子与DAT和血清素转运蛋白（SERT）结合的生物学活性。当比较它们相对于SERT与DAT的结合时，其中一些新的类似物比GBR 12909更有效和更具选择性。因此，化合物9和19a是该系列中最有效的化合物（分别为IC50 = 6.6和6.0 nM）和选择性化合物（DAT / SERT = 33.8和30.0），它们的活性比GBR 12909（IC50 = 14）高nM，DAT / SERT = 6.1）。在这些分子的N-丙基侧链中引入双键不会在很大程度上影响其活性。

  DOI：

  10.1021/jm970595h
• 作为产物：
  描述：

  对氟苯甲酰氯 在 sodium tetrahydroborate 、 三氯化铝 、 水 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 4.0h， 生成 (4-fluorophenyl)-(thiophen-2-yl)-methanol
  参考文献：
  名称：

  Novel 1-[2-(Diarylmethoxy)ethyl]-2-methyl-5-nitroimidazoles as HIV-1 Non-Nucleoside Reverse Transcriptase Inhibitors. A Structure−Activity Relationship Investigation

  摘要：

  1-[2-(Diarylmethoxy)ethyl]-2-methyl-5-nitroimidazoles (DAMNIs) is a novel family of HIV-1 non-nucleoside reverse transcriptase inhibitors (NNRTIs) active at submicromolar concentration. Replacement of one phenyl ring of 1-[2-(diphenylmethoxy)ethyl]-2-methyl-5-nitroimidazole (4) with heterocyclic rings, such as 2-thienyl or 3-pyridinyl, led to novel DAMNIs with increased activity. In HIV-1 WT cell-based assay the racemic 1-{2-{alpha-(thiophen-2-yl)phenylmethoxylethyl}-2-methyl-5-nitroimidazole (7) (EC50 = 0.03 mu M) proved 5 times more active than compound 4. Docking experiments showed that the introduction of a chiral center would not affect the binding of both (R)-7 and (S)-7. The internal scoring function of the Autodock program calculated the same inhibition constant (K-i = 7.9 nM) for the two enantiomers. Compounds 7 (ID50 = 8.25 mu M) were found more active than efavirenz (ID50 = 25 mu M) against the viral RT carrying the K103N mutation, suggesting for these compounds a potential use in efavirenz based anti-AIDS regimens.

  DOI：

  10.1021/jm050273a

文献信息

• Benzylation via Tandem Grignard reaction —iodotrimethylsilane (TMSI) mediated reduction
  作者：Eric J. Stoner、Darlene A. Cothron、Mary K. Balmer、Brian A. Roden

  DOI：10.1016/0040-4020(95)00659-v

  日期：1995.10

  initial formation of biarylmethanols via reaction of aryl Grignards with carbonyl compounds followed by a subsequent reduction with iodotrimethylsilane (TMSI). A number of improvements over existing literature procedures are reported as well as previously unobserved dimenzations. Studies reveal that as few as 3 equiv of TMSI will give complete reduction in most cases where either of the substituents are not

  已经开发出允许大规模制备联芳基甲烷的方法。该方法包括通过芳基格氏试剂与羰基化合物的反应初始形成联芳基甲醇，随后用碘代三甲基硅烷（TMSI）还原。据报道，对现有文献方法以及先前未曾观察到的尺寸进行了许多改进。研究表明，在大多数取代基都不是杂芳族的情况下，只有3当量的TMSI会完全还原。单取代的链烷醇与TMSI反应，得到相应的碘化物。还报道了TMSI减少的机理研究。
• Lewis Acid Catalyzed Cyclization of Propargylic Alcohols with 2-Vinylphenol
  作者：Ya-Ping Han、Xian-Rong Song、Yi-Feng Qiu、Xue-Song Li、Heng-Rui Zhang、Xin-Yu Zhu、Xue-Yuan Liu、Yong-Min Liang

  DOI：10.1021/acs.orglett.6b01875

  日期：2016.8.5

  An unprecedented Lewis acid catalyzed, protection-free, and high-efficiency synthesis of valuable 3,4-dihydro-2H-2,4-methanochromans via cycloaddition of propargylic alkynols with 2-vinylphenol is described. This cycloaddition protocol, which tolerates a wide variety of functional groups, provides practical, versatile, and atom-economical access to a new class of appealing bridged-ring products in

  本文描述了一种空前的路易斯酸，其通过炔丙基炔醇与2-乙烯基苯酚的环加成反应，催化了有价值的3,4-二氢-2 H -2,4-甲烷二甲基苯并没有保护性地进行了高效合成。该环加成方案可耐受多种官能团，以令人满意的收率提供实用，通用且经济实惠的途径来获得新型的有吸引力的桥环产品。与报道的桥环骨架合成反应条件相比，目前的反应条件是中性，温和且没有任何添加剂。
• Arylation of Carbonyl Compounds Catalyzed by Rhodium and Iridium 1,3-R₂-Tetrahydropyrimidin-2-ylidenes: Structure-Reactivity Correlations
  作者：Nicolas Imlinger、Monika Mayr、Dongren Wang、Klaus Wurst、Michael R. Buchmeiser

  DOI：10.1002/adsc.200404176

  日期：2004.12

  reaction of 1.0 equivalents of CF3COOAg with 1. The use of an excess of CF3COOAg resulted in the replacement of Rh(I) by Ag(I) and yielded Ag(1,3-dimesityltetrahydropyrimidin-2-ylidene)+Rh2(CF3COO)3(COD)− (8). Compounds 4 and 8 were characterized by X-ray analysis. The activity of the rhodium complexes increased in the order 5>3>1>2, indicating the necessity of strongly electron-withdrawing groups at the metal

  六个不同的明确定义的铑和铱N-杂环卡宾配合物，即RhCl（1,3-dimesityltetrahydropyrimidin-2- ylidene ）（COD）（1），RhBr（1,3-dimesityltetrahydropyrimidin-2-ylidene）（COD） （2），RhCl [1,3-二（2-丙基）四氢嘧啶-2-亚基]（COD）（3），IrCl（1,3-二甲基四氢嘧啶-2-亚基）（COD）（4），Rh（ CF 3 COO）（1,3-二甲基四氢嘧啶-2-亚基）（COD）（5）和IrBr [1,3-二（2-丙基）四氢嘧啶-2-亚基]（COD）（6）（COD = 1,5-环辛二烯，1,5-环辛二烯= 2,4,6-三甲基苯基）已被用作使用不同的芳基硼酸将醛和α，β-不饱和酮芳基化的催化剂。化合物1– 4和6分别通过[RhCl（COD）] 2和[IrCl（COD）] 2与碱和相应的1
• Rh(1,3-bis(2,4,6-trimethylphenyl)-3,4,5,6-tetrahydropyrimidin-2-ylidene)(COD) tetrafluoroborate, an unsymmetrical Rh-homoazallylcarbene: synthesis, X-ray structure and reactivity in carbonyl arylation and hydrosilylation reactions
  作者：Nicolas Imlinger、Klaus Wurst、Michael R. Buchmeiser

  DOI：10.1016/j.jorganchem.2004.11.057

  日期：2005.10

  The synthesis of novel Rh(1,3-bis(2,4,6-trimethylphenyl)-3,4,5,6-tetrahydropyrimidin-2-ylidene)(COD) tetrafluoroborate (1, COD = η4-1,5-cyclooctadiene) is described. The N-heterocyclic carbene acts as a bidentate ligand with the carbene coordinating to the Rh(I) center and an arene group acting as a homoazallyl ligand. 1 was used in various carbonyl arylation and hydrosilylation reactions allowing

  新颖的Rh的合成（1,3-双（2,4,6-三甲基苯基）-3,4,5,6-四氢嘧啶-2-亚基）（COD）四氟硼酸盐（1，COD =η 4 -1,5- -环辛二烯）。的Ñ -杂环卡宾充当与卡宾配位到的Rh（I）中心和一个芳烃基团充当homoazallyl配体的二齿配体。1被用于各种羰基芳基化和氢化硅烷化反应中，从而以前所未有的选择性和效率形成所需的产物。因此，获得了高达2000的周转数（TONs）。
• 4-(1H-2-methylimidazo[4,5-c]pyridinylmethyl)phenylsulphonamide
  申请人：British Biotech Pharmaceuticals Limited

  公开号：US05516783A1

  公开（公告）日：1996-05-14

  The present invention is directed to compounds of general formula I as well their pharmaceutically and veterinarily acceptable acid addition salts or hydrates thereof. The present invention is further directed to pharmaceutical and veterinary compositions containing the compounds of general formula I. The present compounds of general formula I are antagonist of platelet activating factor (PAF). Accordingly, the present invention is also directed to methods for preventing, treating or ameliorating in human or mammalian animals, various diseases or physiological conditions mediated by PAF.

  本发明涉及一般式I的化合物，以及它们的药用和兽医学上可接受的酸盐或水合物。本发明还涉及含有一般式I化合物的药用和兽医学组合物。一般式I的这些化合物是血小板活化因子（PAF）的拮抗剂。因此，本发明还涉及用于预防、治疗或改善人类或哺乳动物患有的由PAF介导的各种疾病或生理状况的方法。