9-[4-(trifluoromethyl)phenyl]-9H-xanthene-9-ol | 112305-07-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并吡喃
• 英文名称: 9-[4-(trifluoromethyl)phenyl]-9H-xanthene-9-ol
• 英文别名: 9-(4-(trifluoromethyl)phenyl)-9H-xanthen-9-ol；9-(4-trifluoromethylphenyl)xanthen-9-ol；9-(4-trifluorophenyl)xanthen-9-ol；9-[4-(trifluoromethyl)phenyl]xanthen-9-ol
• CAS: 112305-07-4
• 化学式: C₂₀H₁₃F₃O₂
• 分子量: 342.317
• InChiKey: NQLOCEUXWDHPKR-UHFFFAOYSA-N

物化性质

• 熔点：
  169-170 °C
• 沸点：
  438.4±45.0 °C(Predicted)
• 密度：
  1.367±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.7
• 重原子数：
  25
• 可旋转键数：
  1
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.1
• 拓扑面积：
  29.5
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  9-[4-(trifluoromethyl)phenyl]-9H-xanthene-9-ol 以 水 、 乙腈 为溶剂， 生成 9-(p-Trifluoromethylphenyl)xanthyl
  参考文献：
  名称：

  Electrophilic reactions of xanthylium carbocations produced by flash photolysis of 9-xanthenols

  摘要：

  DOI：

  10.1021/ja00190a030
• 作为产物：
  描述：

  占吨酮 、 对溴三氟甲苯 在 正丁基锂 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 反应 28.0h， 以88%的产率得到9-[4-(trifluoromethyl)phenyl]-9H-xanthene-9-ol
  参考文献：
  名称：

  新型l-半胱氨酸衍生物作为强效KSP抑制剂的结构导向设计

  摘要：

  驱动蛋白纺锤体蛋白（KSP），称为Hs Eg5，是驱动蛋白5家族的成员，在双极纺锤体的形成和维持中起着重要作用。我们先前报道了S-三苯甲基-1-半胱氨酸衍生物作为选择性KSP抑制剂。在这里，我们报告了在L5变构结合位点使用对接模型的进一步优化，这导致了在三苯甲基中具有两个稠合苯环的几种高亲和力衍生物的发现，从而产生了低纳摩尔范围的KSP ATPase抑制作用。代表性衍生物在体内与KSP抑制活性相关地有效抑制HCT116细胞的细胞生长，并显着抑制肿瘤生长。

  DOI：

  10.1021/acsmedchemlett.5b00221

文献信息

• Palladium-Catalyzed Dehydroarylation of Triarylmethanols and Their Coupling with Unsaturated Compounds Accompanied by C−C Bond Cleavage
  作者：Yoshito Terao、Michiyo Nomoto、Tetsuya Satoh、Masahiro Miura、Masakatsu Nomura

  DOI：10.1021/jo049031t

  日期：2004.10.1

  Triarylmethanols are effectively dehydroarylated and reacted with some unsaturated compounds by using an appropriate palladium catalyst system such as Pd(OAc)(2)-P(1-Nap)(3) (1-Nap = 1-naphthyl) to give the corresponding arenes and hydroarylation products, respectively, along with diaryl ketones.
• Triarylmethanes and 9-arylxanthenes as prototypes amphihydric compounds for relating the stabilities of cations, anions and radicals by C-H bond cleavage and electron transfer
  作者：Edward M. Arnett、Robert A. Flowers、Richard T. Ludwig、Alison E. Meekhof、Stuart A. Walek

  DOI：10.1002/(sici)1099-1395(199707)10:7<499::aid-poc896>3.0.co;2-2

  日期：1997.7

  Thermodynamic stability properties of II p-substituted trityl and seven 9-phenylxanthyl carbocations are reported in sulfolane and of their conjugate carbanions in DMSO. The cations are compared by calorimetric heats of hydride transfer from cyanoborohydride ion, their first and second reduction potentials, their PK(R)(+)s in aqueous sulfuric acid, C-13 chemical shifts and free energies of methoxy exchange. Carbanlons are compared by their heats and free energies (pK(HA)) of deprotonation and their first and second oxidation potentials. Radicals are compared by their oxidation and reduction potentials. Their bond dissociation energies are derived by alternative routes: from the carbocation and its reduction potential and from the carbanion and its oxidation potential. The various properties are correlated against each other and against appropriate Hammett-type substituent parameters. Correlations between the different measured properties reported here range from fair to excellent, Despite their importance as historic prototypes for the three trivalent oxidation states of carbon, trityl and xanthyl systems are atypical models for comparing transmission of electron demand In other series of carbocations, radicals or carbanions with significantly different structures. The 9-arylxanthyl series is especially poor because of its insensitivity to substituent effects. The effects of substituents on various properties which represent the stabilities of R(+)s correlate surprisingly well against those for corresponding R(-)s. Accordingly, compensating effects on the oxidation and reduction of a series of related RS may lead to a nearly constant electron transfer energy and absolute hardness for the series. In contrast, the free energies for interconversion of the carbocations and carbanions which determine the gap between pK(R+) and pK(HA) are very sensitive to structural change. (C) 1997 by John Wiley & Sons, Ltd.
• KOORTS J.;TALJAARD B.;GOOSEN A., S. AFR. J. CHEM., 1987, 40, N 4, 237-242
  作者：KOORTS J.、TALJAARD B.、GOOSEN A.

  DOI：——

  日期：——
• TALJAARD B.; GOOSEN A.; MCCLELAND C. W., S. AFR. J. CHEM., 40,(1987) N 2, 139-145
  作者：TALJAARD B.、 GOOSEN A.、 MCCLELAND C. W.

  DOI：——

  日期：——
• Structure-Guided Design of Novel <scp>l</scp>-Cysteine Derivatives as Potent KSP Inhibitors
  作者：Naohisa Ogo、Yoshinobu Ishikawa、Jun-ichi Sawada、Kenji Matsuno、Akihiro Hashimoto、Akira Asai

  DOI：10.1021/acsmedchemlett.5b00221

  日期：2015.9.10

  previously reported S-trityl-l-cysteine derivatives as selective KSP inhibitors. Here, we report further optimizations using docking modeling in the L5 allosteric binding site, which led to the discovery of several high affinity derivatives with two fused phenyl rings in the trityl group giving low nanomolar range KSP ATPase inhibition. The representative derivatives potently inhibited cell growth of HCT116

  驱动蛋白纺锤体蛋白（KSP），称为Hs Eg5，是驱动蛋白5家族的成员，在双极纺锤体的形成和维持中起着重要作用。我们先前报道了S-三苯甲基-1-半胱氨酸衍生物作为选择性KSP抑制剂。在这里，我们报告了在L5变构结合位点使用对接模型的进一步优化，这导致了在三苯甲基中具有两个稠合苯环的几种高亲和力衍生物的发现，从而产生了低纳摩尔范围的KSP ATPase抑制作用。代表性衍生物在体内与KSP抑制活性相关地有效抑制HCT116细胞的细胞生长，并显着抑制肿瘤生长。