diphenyl(3-(trifluoromethyl)phenyl)methanol | 742-91-6

• 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: diphenyl(3-(trifluoromethyl)phenyl)methanol
• 英文别名: diphenyl-(3-trifluoromethyl-phenyl)-methanol；Diphenyl-(3-trifluormethyl-phenyl)-methanol；3-Trifluormethyl-triphenyl-carbinol；alpha,alpha-Diphenyl-3-(trifluoromethyl)benzenemethanol；diphenyl-[3-(trifluoromethyl)phenyl]methanol
• CAS: 742-91-6
• 化学式: C₂₀H₁₅F₃O
• 分子量: 328.334
• InChiKey: BGWMCPSZICGSBS-UHFFFAOYSA-N

物化性质

• 熔点：
  52-54 °C
• 沸点：
  140-142 °C(Press: 0.5 Torr)
• 密度：
  1.244±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.6
• 重原子数：
  24
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.1
• 拓扑面积：
  20.2
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  diphenyl(3-(trifluoromethyl)phenyl)methanol 在 aniline hydrochloride 、 溶剂黄146 作用下， 生成 triphenyl-(3-trifluoromethyl-phenyl)-methane
  参考文献：
  名称：

  Aromatic Substitution by a Highly Selective Radical—Triphenylmethyl. A Case of a Free Radical Reaction in Which Nitrobenzene Is Essentially Unreactive

  摘要：

  DOI：

  10.1021/ja01546a032
• 作为产物：
  描述：

  1-(Diphenylmethyl)-3-(trifluoromethyl)benzene 在 水 作用下， 以 乙腈 为溶剂， 生成 diphenyl(3-(trifluoromethyl)phenyl)methanol
  参考文献：
  名称：

  通过激光闪光光解研究三芳基甲基和二芳基甲基阳离子与叠氮离子的反应性。扩散控制反应

  摘要：

  通过使用激光闪光光解技术，已经直接测量了在 20 o C 下在 18 个三芳基甲基和 10 个二芳基甲基阳离子与叠氮化物的不同组成的乙腈-水 (AN-W) 溶液中反应的速率常数 k AZ 和 k S和溶剂。阳离子具有取决于取代基的k S 并且从～10 1 到～10 7 s -1 变化。对于更稳定的离子，k AZ 也发生变化，随着给电子量的减少而增加，并且随着乙腈含量的增加而增加多达10 3 。然而，对于不太稳定的阳离子，速率常数与取代基无关

  DOI：

  10.1021/ja00003a040

文献信息

• Protolytic defluorination of trifluoromethyl-substituted arenes
  作者：Anila Kethe、Adam F. Tracy、Douglas A. Klumpp

  DOI：10.1039/c0ob01276a

  日期：——

  Bronsted superacids. The products from these reactions suggest the formation of reactive electrophiles, such as carbocations, acylium cations or equivalent electrophilic species. As such, Friedel-Crafts-type reactions occur between these species and arene nucleophiles. NMR studies were done, and the results suggest the formation of an acyl group from the trifluoromethyl groups in the superacid.

  研究了一系列三氟甲基取代的芳烃与布朗斯台德超强酸的反应。这些反应的产物表明反应性亲电试剂的形成，例如碳正离子、酰基阳离子或等效的亲电物质。因此，Friedel-Crafts 型反应发生在这些物种和芳烃亲核试剂之间。进行了核磁共振研究，结果表明超强酸中的三氟甲基形成了酰基。
• 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.
• Acidities and homolytic bond dissociation energies (BDEs) of benzyl-type carbon-hydrogen bonds in sterically congested substrates
  作者：F. G. Bordwell、Jin Pei Cheng、A. V. Satish、Cary L. Twyman

  DOI：10.1021/jo00050a032

  日期：1992.11

  Equilibrium acidities in DMSO and BDEs for the benzylic C-H bonds are reported for 19 triphenylmethanes, three 9,10-dihydroanthracenes, and nine xanthenes. The phenyl groups in triphenylmethane, 9-phenyl-9,10-dihydroanthracene, and 9-phenylxanthene are shown to be constrained in their ability to delocalize either the negative charges in the anions formed by loss of a proton or the odd electrons released by loss of hydrogen atom. Analysis of the pK(HA) values showed, however, that strong solvation of para electron-withdrawing substituents in a phenyl ring of each of these substrates caused the corresponding anion to adopt a conformation where effective conjugative overlap occurred between the substituent and the carbanion via the phenyl ring. In other words, a conformational change was induced via a substituent solvation assisted resonance (SSAR) effect. In sharp contrast to these large solvation-induced substituent effects on anion stabilities, remote substituent effects on radical stabilities in these congested species were found to be negligible. Substitution of either a p-toluenesulfonyl or CN group into the 9-position of xanthene caused a large increase in acidity, but the p-CH3C6H4SO2 group caused an increase in the BDE of the acidic C-H bond, whereas the CN group caused a small decrease.
• YAMATAKA, HIROSHI;KAWAFUJI, YUKIE;NAGAREDA, KATSUSHI;MIYANO, NOBUTAKA;HAN+, J. ORG. CHEM., 54,(1989) N9, C. 4706-4708
  作者：YAMATAKA, HIROSHI、KAWAFUJI, YUKIE、NAGAREDA, KATSUSHI、MIYANO, NOBUTAKA、HAN+

  DOI：——

  日期：——
• US7235577B1
  申请人：——

  公开号：US7235577B1

  公开（公告）日：2007-06-26