3-fluorotriphenylmethanol | 427-35-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 三苯基化合物
• 英文名称: 3-fluorotriphenylmethanol
• 英文别名: m-Fluorphenyldiphenylcarbinol；(3-fluorophenyl)(diphenyl)methanol；(3-Fluor-phenyl)-diphenyl-methanol；Hydroxy-diphenyl-(3-fluor-phenyl)-methan；(3-Fluorophenyl)-diphenylmethanol
• CAS: 427-35-0
• 化学式: C₁₉H₁₅FO
• 分子量: 278.326
• InChiKey: UMCOHLWADNTYJJ-UHFFFAOYSA-N

物化性质

• 熔点：
  117 °C
• 沸点：
  411.7±40.0 °C(Predicted)
• 密度：
  1.186±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.3
• 重原子数：
  21
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.05
• 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-fluorotriphenylmethanol 在 氨 、 氢溴酸 作用下， 以 溶剂黄146 、 苯 为溶剂， 生成 m-Fluorphenyldiphenylaminomethan
  参考文献：
  名称：

  19F substituent chemical shifts of the fluorophenyldiphenylsilanes and the carbon analogs

  摘要：

  DOI：

  10.1016/s0022-328x(00)84996-7
• 作为产物：
  描述：

  二苯甲酮 、 alkaline earth salt of/the/ methylsulfuric acid 在 乙醚 作用下， 生成 3-fluorotriphenylmethanol
  参考文献：
  名称：

  The Dissociation of Hexaarylethanes. XVI.¹ Alkyl and Halogen Derivatives

  摘要：

  DOI：

  10.1021/ja01234a023

文献信息

• Steric and Electronic Effects Influencing β-Aryl Elimination in the Pd-catalyzed Carbon–Carbon Single Bond Activation of Triarylmethanols
  作者：James R. Bour、Jacob C. Green、Valerie J. Winton、Jeffrey B. Johnson

  DOI：10.1021/jo302592g

  日期：2013.2.15

  An analysis of the palladium-catalyzed activation of carbon–carbon single bonds within triarylmethanols has led to a greater understanding of factors influencing the β-aryl elimination process responsible for C–C bond cleavage. A series of competition reactions were utilized to determine that β-aryl elimination of aryl substituents containing ortho-substitution proceeds with significant preference

  对钯催化的三芳基甲醇中碳-碳单键活化的分析，导致人们对影响影响C-C键断裂的β-芳基消除过程的因素有了更深入的了解。利用一系列竞争反应来确定β-芳基消除含有邻位取代基的芳基取代基比未取代的苯环显着地优先进行。进一步的实验表明，与相对中性的物质相比，含有强供体或撤离取代基的底物更容易从三芳基甲醇中裂解出来。
• A Novel Synthesis of Soluble, Stable Derivatives of the Perchlorinated Trityl Radical
  作者：Richard J. Bushby

  DOI：10.1002/ejoc.202301136

  日期：2024.2.26

  Chlorination of the fluorinated triarylmethane is followed by selective nucleophilic substitution using the sodium salt of n-hexanol in n-hexanol/dimethylsulfoxide and conversion to the radical.

  氟化三芳基甲烷氯化后，使用正己醇/二甲亚砜中的正己醇钠盐进行选择性亲核取代并转化为自由基。
• Bartroli; Alguero; Boncompte, Arzneimittel-Forschung/Drug Research, 1992, vol. 42, # 6, p. 832 - 835
  作者：Bartroli、Alguero、Boncompte、Forn

  DOI：——

  日期：——
• Triphenylbutanamines: Kinesin Spindle Protein Inhibitors with in Vivo Antitumor Activity
  作者：Fang Wang、James A. D. Good、Oliver Rath、Hung Yi Kristal Kaan、Oliver B. Sutcliffe、Simon P. Mackay、Frank Kozielski

  DOI：10.1021/jm201195m

  日期：2012.2.23

  The human mitotic kinesin Eg5 represents a novel mitotic spindle target for cancer chemotherapy. We previously identified S-trityl-L-cysteine (STLC) and related analogues as selective potent inhibitors of Eg5. We herein report on the development of a series of 4,4,4-triphenylbutan-1-amine inhibitors derived from the STLC scaffold. This new generation systematically improves on potency: the most potent C-trityl analogues exhibit K-i(aPP) <= 10 nM and GI(50) approximate to 50 nM, comparable to results from the phase II clinical benchmark ispinesib. Crystallographic studies reveal that they adopt the same overall binding configuration as S-trityl analogues at an allosteric site formed by loop L5 of Eg5. Evaluation of their druglike properties reveals favorable profiles for future development and, in the clinical candidate ispinesib, moderate hERG and CYP inhibition. One triphenylbutanamine analogue and ispinesib possess very good bioavailability (51% and 45%, respectively), with the former showing in vivo antitumor growth activity in nude mice xenograft studies.
• Andrews, Adrian F.; Mackie, Raymond K.; Walton, John C., Journal of the Chemical Society. Perkin transactions II, 1980, p. 96 - 102
  作者：Andrews, Adrian F.、Mackie, Raymond K.、Walton, John C.

  DOI：——

  日期：——