1-[3,5-双(三氟甲基)苯基]-1-苯基甲醇 | 81390-93-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 中文名称: 1-[3,5-双(三氟甲基)苯基]-1-苯基甲醇
• 英文名称: (3,5-bis(trifluoromethyl)phenyl)(phenyl)methanol
• 英文别名: [3,5-bis(trifluoromethyl)phenyl]-phenylmethanol
• CAS: 81390-93-4
• 化学式: C₁₅H₁₀F₆O
• 分子量: 320.234
• InChiKey: IJECXTZHVDMNGS-UHFFFAOYSA-N

物化性质

• 熔点：
  74.9-75.5 °C
• 沸点：
  286.2±35.0 °C(Predicted)
• 密度：
  1.367±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.5
• 重原子数：
  22
• 可旋转键数：
  2
• 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：
  7

反应信息

• 作为反应物：
  描述：

  1-[3,5-双(三氟甲基)苯基]-1-苯基甲醇 在 4-苯偶氮二苯胺 、 lithium hexamethyldisilazane 作用下， 以 四氢呋喃 为溶剂， 生成 3-(3,5-bis-trifluoromethyl-phenyl)-3-phenyl-propionitrile
  参考文献：
  名称：

  在苯甲基中心的亲核取代：1，1-二芳基烷基衍生物的不对称合成。

  摘要：

  [反应：见正文]活化1，1-二芳基甲醇作为相应的甲苯磺酸盐，然后用一系列碳，氮，氧和硫亲核试剂取代，收率为81-96％。活化对映体富集的二芳基甲醇8a-c，并用乙酸烯醇吡啶酯置换，在碳上完全立体化学转化，得到1，1-二芳基烷基衍生物10a-c，而没有光学纯度的损失。

  DOI：

  10.1021/ol0361655
• 作为产物：
  描述：

  3,5-双三氟甲基苯甲醛 、 苯基锂 以 四氢呋喃 为溶剂， 以92%的产率得到1-[3,5-双(三氟甲基)苯基]-1-苯基甲醇
  参考文献：
  名称：

  Diaryl hydroxylamines as pan or dual inhibitors of indoleamine 2,3-dioxygenase-1, indoleamine 2,3-dioxygenase-2 and tryptophan dioxygenase

  摘要：

  Tryptophan (Trp) catabolizing enzymes play an important and complex role in the development of cancer. Significant evidence implicates them in a range of inflammatory and immunosuppressive activities. Whereas inhibitors of indoleamine 2,3-dioxygenase-1 (IDO1) have been reported and analyzed in the clinic, fewer inhibitors have been described for tryptophan dioxygenase (TDO) and indoleamine 2,3-dioxygenase-2 (IDO2) which also have been implicated more recently in cancer, inflammation and immune control. Consequently the development of dual or pan inhibitors of these Trp catabolizing enzymes may represent a therapeutically important area of research. This is the first report to describe the development of dual and pan inhibitors of IDO1, TDO and IDO2. (C) 2018 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2018.11.010

文献信息

• A New Route to Acyclic Diaminocarbenes via Lithium−Halogen Exchange
  作者：David R. Snead、Ion Ghiviriga、Khalil A. Abboud、Sukwon Hong

  DOI：10.1021/ol9013156

  日期：2009.8.6

  (ADC) from chloroamidinium salts. Convenient access to various ADC complexes (B, Rh, Ir, Pd) stems from a one-pot transmetalation protocol. Formation of a carbenoid species is suggested by 1D and 2D NMR studies with a 13C-labeled chloroamidinium precursor and also by X-ray structures of transition metal−carbene complexes. Rh-ADC complex 4 is an effective catalyst for the 1,2-addition of aryl boronic acids

  已开发出锂-卤素交换路线，可从氯ami盐生成无环二氨基卡宾（ADC）。方便地访问各种ADC配合物（B，Rh，Ir，Pd）来自于一锅式金属转移协议。通过13 C标记的氯ami鎓前体的1D和2D NMR研究以及过渡金属-卡宾配合物的X射线结构，表明类胡萝卜素物质的形成。Rh-ADC配合物4是芳基硼酸1,2-加成芳基醛的有效催化剂。
• Selective Late‐Stage Hydrodefluorination of Trifluoromethylarenes: A Facile Access to Difluoromethylarenes
  作者：Socrates B. Munoz、Chuanfa Ni、Zhe Zhang、Fang Wang、Nan Shao、Thomas Mathew、George A. Olah、G. K. Surya Prakash

  DOI：10.1002/ejoc.201700396

  日期：2017.4.26

  A selective reductive monodefluorination reaction of trifluoromethyl arenes was developed. Mediated by magnesium metal, various difluoromethylated aromatics were accessed at room temperature in the presence of acetic acid. This protocol shows tolerance to a wide range of functional groups and it was applicable in late-stage hydrodefluorination of complex pharmaceutical compounds, affording the corresponding

  开发了三氟甲基芳烃的选择性还原单脱氟反应。在金属镁的介导下，在乙酸存在下，在室温下获得各种二氟甲基化芳烃。该协议显示出对多种官能团的耐受性，它适用于复杂药物化合物的后期加氢脱氟，提供相应的 CF2H 类似物及其氘化 (CF2D) 对应物。
• Synthesis of 1,1′-Diarylethanes and Related Systems by Displacement of Trichloroacetimidates with Trimethylaluminum
  作者：Nivedita S. Mahajani、John D. Chisholm

  DOI：10.1021/acs.joc.8b00027

  日期：2018.4.6

  Benzylic trichloroacetimidates are readily displaced by trimethylaluminum under Lewis acid promoted conditions to provide the corresponding methyl substitution product. This method is a convenient way to access 1,1′-diarylethanes and related systems, which play a significant role in medicinal chemistry, with a number of systems owing their biological activity to this functionality. Most benzylic substrates

  在路易斯酸促进的条件下，三氯乙酰亚胺酸苄酯很容易被三甲基铝取代，以提供相应的甲基取代产物。该方法是获取 1,1'-二芳基乙烷和相关系统的便捷方法，这些系统在药物化学中发挥着重要作用，许多系统的生物活性归功于此功能。大多数苄基底物都会发生位移，但缺电子系统除外。对映体纯亚氨酸酯的使用显示出显着的外消旋作用，表明形成了阳离子中间体。
• Two-component boronic acid catalysis for increased reactivity in challenging Friedel–Crafts alkylations with deactivated benzylic alcohols
  作者：Hwee Ting Ang、Jason P. G. Rygus、Dennis G. Hall

  DOI：10.1039/c9ob01043b

  日期：——

  report the use of perfluoropinacol as an effective co-catalyst to improve the reactivity of a boronic acid catalyst in the Friedel-Crafts benzylations of electronically deactivated primary and secondary benzylic alcohols. According to spectroscopic studies, it is believed that perfluoropinacol condenses with the arylboronic acid catalyst to form a highly electrophilic and Lewis acidic boronic ester. This

  先前已经开发出一种通用且有效的硼酸催化苯并芳烃的芳烃的弗瑞德-克来福特烷基化反应，用于构造不对称的二芳基甲烷产物（X. Mo，J. Yakiwchuk，J. Dansereau，JA McCubbin和DG Hall，J. Am。Chem （Soc。，2015，137，9694）。然而，由于CO键电离的难度增加，高度缺乏电子的苯甲醇是无效的偶联伴侣。在这里，我们报道了全氟频哪醇作为一种有效的助催化剂，用于提高电子减活的伯和仲苄醇的Friedel-Crafts苄基化反应中硼酸催化剂的反应性。根据光谱学研究，认为全氟频哪醇与芳基硼酸催化剂缩合形成高度亲电和路易斯酸性的硼酸酯。
• Direct allylation of benzyl alcohols, diarylmethanols, and triarylmethanols mediated by XtalFluor-E
  作者：Thomas Lebleu、Jean-François Paquin

  DOI：10.1016/j.tetlet.2016.12.056

  日期：2017.2

  We report the direct allylation of benzyl alcohols, diarylmethanols and triarylmethanols mediated by XtalFluor-E using allyltrimethylsilane. The resulting allylated products are obtained in moderate to high yield.

  我们报告了XtalFluor-E使用烯丙基三甲基硅烷介导的苄醇，二芳基甲醇和三芳基甲醇的直接烯丙基化。以中等至高收率获得所得的烯丙基化产物。