3-(4-fluorophenyl)-3-phenylpropan-1-ol | 374724-94-4

• 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: 3-(4-fluorophenyl)-3-phenylpropan-1-ol
• 英文别名: 3-(4-fIuorophenyl)-3-phenylpropan-1-ol；3-Phenyl-3-(4-fluorophenyl)-propan-1-ol
• CAS: 374724-94-4
• 化学式: C₁₅H₁₅FO
• 分子量: 230.282
• InChiKey: QONXDZSXWWGDIQ-UHFFFAOYSA-N

物化性质

• 沸点：
  177 °C(Press: 15 Torr)
• 密度：
  1.127±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  17
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  20.2
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  3-(4-fluorophenyl)-3-phenylpropan-1-ol 在 4-二甲氨基吡啶 、 氯化亚砜 、 氨 、 potassium iodide 作用下， 以 二氯甲烷 、 二甲基亚砜 为溶剂， -30.0~95.0 ℃ 、2.6 MPa 条件下， 反应 191.0h， 生成 2-[2-[2-[3-(4-fluorophenyl)-3-phenylpropyl]-1H-imidazol-5-yl]ethyl]isoindole-1,3-dione
  参考文献：
  名称：

  Ring-substituted histaprodifen analogues as partial agonists for histamine H1 receptors: synthesis and structure–activity relationships

  摘要：

  Thirteen racemic benzene ring-substituted analogues of histaprodifen (8a; 2-[2-(3,3-diphenylpropyl)-1H-imidazol-4-yl]ethanamine), a novel lead for potent and selective histamine H-1-receptor agonists, have been prepared from substituted 4,4-diphenylbutyronitriles 5 via cyclization of the corresponding methyl butyrimidates 6 with 2-oxo-4-phthalimido-1-butyl acetate in liquid ammonia, followed by deprotection. Nitriles 5 were accessible by alkylation of either substituted diphenylmethanes with 3-bromopropionitrile or diethyl malonate with substituted 1-chloro-diphenylmethanes and subsequent standard reactions. The title compounds 8 displayed partial agonism on contractile H-1 receptors of the guinea-pig ileum (E-max = 2-98% relative to histamine) and, compared with the endogenous agonist, were endowed with agonist potencies of 4-92%. The meta fluorinated (gc) and meta chlorinated (8f) analogues showed the highest relative potency in this series (95% confidence Limits 85-99% and 78-102%), but did not exceed the value of the lead 8a (99-124%). Compound 8c (2-[2-[3-(3-fluorophenyl)-3-phenylpropyl]-1H-imidazol-4-yl]ethanamine) was a partial agonist at contractile H-1 receptors of the guinea-pig aorta (relative potency 154% vs. 100% for histamine) and at relaxation-mediating endothelial H-1 receptors of the rat aorta (relative potency 556% vs. 100% for histamine) and matched with the functional behaviour of 8a. Agonism observed for each compound was sensitive to blockade by the selective H-1-receptor antagonist mepyramine (pA(2) approximate to 9 (guinea-pig) and pA(2) approximate to 8 (rat aorta)). All histaprodifen analogues 8 stimulated neither histaminergic H-2/H-3, nor cholinergic M-3 receptors. They displayed only low to moderate affinity for these sites (H-2: pD'(2), < 5; H-3/M-3: pA(2) < 6). With regard to the substitution pattern on the benzene ring, there was no correlation between the histaprodifen series and the corresponding derivatives of another selective H-1-receptor agonist, viz. 2-phenylhistamine. (C) 2000 Editions scientifiques et medicales Elsevier SAS.

  DOI：

  10.1016/s0223-5234(00)00105-7
• 作为产物：
  描述：

  4-fluorocinnamyl bromide 在 硼烷四氢呋喃络合物 、 C₄₅H₄₂ClCuN₂ 作用下， 以 四氢呋喃 、 正己烷 、 二氯甲烷 、 二丁醚 为溶剂， 反应 2.17h， 生成 3-(4-fluorophenyl)-3-phenylpropan-1-ol
  参考文献：
  名称：

  通过铜催化的不对称烯丙基化与有机锂化合物的手性二芳基甲烷

  摘要：

  提出了高度对映选择性的铜/ N-杂环卡宾与有机锂化合物的烯丙基芳基化反应。在与烯丙基溴的反应中使用市售或易于制备的芳基锂试剂可提供高收率的多种手性二芳基乙烯基甲烷，其在药物中具有优先的结构基序，具有良好或优异的区域和对映选择性。市售药物托特罗定（Detrol）的正式合成中说明了这种新转变的多功能性。

  DOI：

  10.1021/acs.orglett.5b03396

文献信息

• [EN] REAGENTS AND PROCESS FOR DIRECT C-H FUNCTIONALIZATION<br/>[FR] RÉACTIFS ET PROCÉDÉ POUR LA FONCTIONNALISATION DIRECTE DE LA LIAISON C-H
  申请人：STUDIENGESELLSCHAFT KOHLE MBH

  公开号：WO2020094673A1

  公开（公告）日：2020-05-14

  Thianthrene derivative of the Formula (I): wherein R1 to R8 may be the same or different and are selected from hydrogen, Cl, F, a partially or fully fluorinated C1 to C6 alkyl group, and wherein n is 0 or 1, with the proviso that at least one of R1 to R8 is not hydrogen and process for C-H functionalization of aromatic compounds using this compound.

  Thianthrene衍生物的化学式（I）：其中R1到R8可以相同也可以不同，并且选择自氢、Cl、F、部分或完全氟化的C1到C6烷基基团，其中n为0或1，但R1到R8中至少有一个不是氢，并且使用该化合物进行芳香化合物的C-H官能团化的方法。
• Chiral dihydrobenzo[1,4]oxazines as catalysts for the asymmetric transfer-hydrogenation of α,β-unsaturated aldehydes
  作者：Christian Ebner、Andreas Pfaltz

  DOI：10.1016/j.tet.2011.10.051

  日期：2011.12

  A new class of organocatalysts based on the structure of 2,3-dihydrobenzo[1,4]oxazine was prepared and applied in the enantioselective transfer-hydrogenation of α,β-unsaturated aldehydes with Hantzsch ester as hydride donor. These catalysts proved to be particularly effective for the conjugate reduction of β,β-diaryl-substituted acrylaldehydes leading to saturated aldehydes bearing a stereogenic center

  制备了一种基于2,3-二氢苯并[1,4]恶嗪结构的新型有机催化剂，并将其用于以Hantzsch酯为氢化物供体的α，β-不饱和醛的对映选择性转移加氢。这些催化剂被证明对于共轭还原β，β-二芳基取代的丙烯醛特别有效，从而导致带有两个立体不同的芳基的立体异构中心的立体醛，对映选择性高达91％ee。
• Pharmaceutically active piperidine derivatives, in particular as modulators of chemokine receptor activity
  申请人：——

  公开号：US20040006081A1

  公开（公告）日：2004-01-08

  Compounds of formula (I), compositions comprising them, processes for preparing them and their use in medical therapy (for example modulating CCR5 receptor activity in a warm blooded animal).

  式(I)的化合物，包含它们的组合物，制备它们的方法以及它们在医学疗法中的使用（例如在温血动物中调节CCR5受体活性）。
• Photoredox catalysis with aryl sulfonium salts enables site-selective late-stage fluorination
  作者：Jiakun Li、Junting Chen、Ruocheng Sang、Won-Seok Ham、Matthew B. Plutschack、Florian Berger、Sonia Chabbra、Alexander Schnegg、Christophe Genicot、Tobias Ritter

  DOI：10.1038/s41557-019-0353-3

  日期：2020.1

  leaving groups as those valuable in conventional cross-coupling catalysis, such as bromide. Yet the redox potentials of common photoredox catalysts are not sufficient to reduce most aryl bromides, so synthetically useful aryl radicals are often not directly available. Therefore, the development of a distinct leaving group more appropriately matched in redox potential could enable new reactivity manifolds

  光氧化还原催化，特别是与过渡金属催化结合，可以产生过渡金属催化剂的氧化还原态，以促进在传统氧化还原催化中不易获得的具有挑战性的键形成。对于芳烃官能化，金属光氧化还原催化已成功利用与在常规交叉偶联催化中有价值的那些离去基团相同的离去基团，例如溴化物。然而，普通的光氧化还原催化剂的氧化还原电势不足以还原大多数芳基溴化物，因此合成上有用的芳基常常不能直接获得。因此，在氧化还原电势上更合适地匹配一个独特的离去基团的开发，可以为金属光氧化还原催化提供新的反应性流形，特别是如果芳基铜（III）配合物可及的话，从中可以发生最具挑战性的成键反应。在这里，我们显示了芳基ian盐在金属光氧化还原催化方面的概念优势，以及它们在定点选择性后期芳族氟化反应中的效用。
• PHARMACEUTICALLY ACTIVE PIPERIDINE DERIVATIVES, IN PARTICULAR AS MODULATORS OF CHEMOKINE RECEPTOR ACTIVITY
  申请人：AstraZeneca AB

  公开号：EP1289957A1

  公开（公告）日：2003-03-12