2-(三氟甲基)呫吨酮 | 1496-15-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并吡喃
• 中文名称: 2-(三氟甲基)呫吨酮
• 英文名称: 2-trifluoromethyl-9H-xanthen-9-one
• 英文别名: 2-(Trifluoromethyl)xanthone；2-(trifluoromethyl)xanthen-9-one
• CAS: 1496-15-7
• 化学式: C₁₄H₇F₃O₂
• 分子量: 264.204
• InChiKey: LEOGBDMNMFJKRV-UHFFFAOYSA-N

物化性质

• 熔点：
  121-122°C
• 沸点：
  359.0±42.0 °C(Predicted)
• 密度：
  1.411±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.3
• 重原子数：
  19
• 可旋转键数：
  0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  5

安全信息

• 危险等级：
  IRRITANT
• 危险品标志：
  Xi
• 安全说明：
  S26
• 危险类别码：
  R36/37/38
• 海关编码：
  2932999099

反应信息

• 作为反应物：
  描述：

  2-(三氟甲基)呫吨酮 生成 9-(1-methyl-piperidin-4-yl)-2-trifluoromethyl-xanthen-9-ol
  参考文献：
  名称：

  Pharmaceutical compositions and method of producing anti-psychotic

  摘要：

  三环哌啶基衍生物在动物宿主内部以治疗有效剂量给药，能产生抗精神病活性，而不会出现锥体外症状。其中一些活性成分是新颖的化合物本身。

  公开号：

  US04086350A1
• 作为产物：
  描述：

  占吨酮 在 tris(2,2-bipyridine)ruthenium(II) hexafluorophosphate 、 三氟乙酸酐 作用下， 以 乙腈 为溶剂， 30.0 ℃ 、101.33 kPa 条件下， 反应 15.0h， 生成 2-(三氟甲基)呫吨酮
  参考文献：
  名称：

  用于位点选择性晚期三氟甲基化的芳基S盐。

  摘要：

  已经发现将CF 3基团掺入芳烃在药物发现中的重要性日益增加。在本文中，我们报道了芳基ian盐与铜基三氟甲基试剂的首次光氧化还原催化交叉偶联，这使得芳烃的位点选择性后期三氟甲基化成为可能。该反应以宽泛的官能团耐受性进行，即使对于克级的复杂小分子也是如此。该方法进一步扩展到生产五氟乙基化衍生物。

  DOI：

  10.1002/anie.201906672

文献信息

• MODULATORS OF GLUCOCORTICOID RECEPTOR, AP-1, AND/OR NF-kB ACTIVITY AND USE THEREOF
  申请人：Weinstein David S.

  公开号：US20090075995A1

  公开（公告）日：2009-03-19

  Novel non-steroidal compounds are provided which are useful in treating diseases associated with modulation of the glucocorticoid receptor, AP-1, and/or NF-κB activity, including inflammatory and immune diseases, having the structure of formula (I): an enantiomer, diastereomer, or tautomer thereof, or a prodrug ester thereof, or a pharmaceutically-acceptable salt thereof, in which: Z is heterocyclo or heteroaryl; A is a 5- to 8-membered carbocyclic ring or a 5- to 8-membered heterocyclic ring; B is a cycloalkyl, cycloalkenyl, aryl, heterocyclo, or heteroaryl ring, wherein each ring is fused to the A ring on adjacent atoms and optionally substituted by one to four groups which are the same or different and are independently selected from R 5 , R 6 , R 7 , and R 8 ; J 1 , J 2 , and J 3 are at each occurrence the same or different and are independently -A 1 QA 2 -; Q is a bond, O, S, S(O), or S(O) 2 ; A 1 and A 2 are the same or different and are at each occurrence independently selected from a bond, C 1-3 alkylene, substituted C 1-3 alkylene, C 2-4 alkenylene, and substituted C 2-4 alkenylene, provided that A 1 and A 2 are chosen so that ring A is a 5- to 8-membered carbocyclic or heterocyclic ring; R 1 to R 11 are as defined herein. Also provided are pharmaceutical compositions and methods of treating inflammatory- or immune-associated diseases and obesity and diabetes employing said compounds.

  提供了一系列新颖的非甾体化合物，这些化合物在治疗与糖皮质激素受体、AP-1和/或NF-κB活性调节相关的疾病中很有用，包括炎性和免疫疾病，具有以下结构式（I）： 其对应的光学异构体、对映异构体或互变异构体，或其前药酯，或其药用可接受盐，其中： Z是杂环或杂芳基； A是一个5至8成员的碳环或一个5至8成员的杂环； B是一个环烷基、环烯基、芳基、杂环或杂芳基环，其中每个环都与A环上的相邻原子融合，并且可以选择性地被一个到四个独立选自R5、R6、R7和R8的相同或不同的组取代； J1、J2和J3每次出现时相同或不同，独立地选自-A1QA2-；Q是键、O、S、S(O)或S(O)2；A1和A2相同或不同，每次出现时独立地选自键、C1-3烷基、取代的C1-3烷基、C2-4烯基和取代的C2-4烯基，前提是A1和A2的选择使得环A是一个5至8成员的碳环或杂环； R1至R11如本文所述定义。 还提供了使用这些化合物的药物组合物和治疗炎性疾病、免疫相关疾病、肥胖和糖尿病的方法。
• An Aryl to Imidoyl Palladium Migration Process Involving Intramolecular C−H Activation
  作者：Jian Zhao、Dawei Yue、Marino A. Campo、Richard C. Larock

  DOI：10.1021/ja070657l

  日期：2007.4.1

  imidoyl palladium migration, followed by intramolecular arylation. The fluoren-9-one synthesis appears to involve both a palladium migration mechanism and a C-H activation process proceeding through an unprecedented organopalladium(IV) hydride intermediate. The results from deuterium labeling experiments are consistent with the proposed dual mechanism.

  具有生物学意义的 fluoren-9-one 和 xanthen-9-one 衍生物已通过新型芳基到亚胺酰基钯的迁移，然后进行分子内芳基化制备。芴 9-one 合成似乎涉及钯迁移机制和 CH 活化过程，该过程通过前所未有的有机钯 (IV) 氢化物中间体进行。氘标记实验的结果与提出的双重机制一致。
• Concise synthesis of xanthones by the tandem etherification—Acylation of diaryliodonium salts with salicylates
  作者：Gaoxiaozheng Liu、Chao Wu、Bifeng Chen、Ru He、Chao Chen

  DOI：10.1016/j.cclet.2017.11.046

  日期：2018.6

  Abstract An efficient synthetic method for multi-substituted xanthones was developed. The reaction of diaryliodonium salts and salicylates was employed for the preparation of the xanthones. This method proceeded through an intermolecular etherification-acylation to give target heterocycles in good yields (up to 91%). Multi-substituted xanthones were gained by shifting the substituent of salicylates or

  摘要建立了一种高效的多取代氧杂蒽合成方法。将二芳基碘鎓盐和水杨酸酯的反应用于制备氧杂蒽。此方法通过分子间醚化酰化进行，以高收率（最高91％）得到目标杂环。通过取代水杨酸盐或二芳基碘鎓盐的取代基获得多取代的氧杂蒽
• One-Step Synthesis of Xanthones Catalyzed by a Highly Efficient Copper-Based Magnetically Recoverable Nanocatalyst
  作者：Cintia A. Menéndez、Fabiana Nador、Gabriel Radivoy、Darío C. Gerbino

  DOI：10.1021/ol500964e

  日期：2014.6.6

  A versatile and highly efficient strategy to construct a xanthone skeleton via a ligand-free intermolecular catalytic coupling of 2-substituted benzaldehydes and a wide range of phenols has been developed. For this purpose, a novel and magnetically recoverable catalyst consisting of copper nanoparticles on nanosized silica coated maghemite is presented. The reaction proceeds smoothly with easy recovery

  已经开发了通过2-取代的苯甲醛与多种酚的无配体分子间催化偶联来构建黄酮骨架的通用且高效的策略。为此，提出了一种新颖的且可磁回收的催化剂，该催化剂由纳米级二氧化硅涂覆的磁赤铁矿上的铜纳米颗粒组成。反应平稳进行，催化剂易于回收和再利用。该方法与各种功能基团兼容，并提供了一个诱人的方案，可用于以很高的产率生成小量的氧杂蒽酮。
• FeCl₃and ether mediated direct intramolecular acylation of esters and their application in efficient preparation of xanthone and chromone derivatives
  作者：Neng Jiang、Su-Yi Li、Sai-Sai Xie、Hequan Yao、Hongbin Sun、Xiao-Bing Wang、Ling-Yi Kong

  DOI：10.1039/c4ra10174j

  日期：——

  The direct intramolecular acylation of esters was developed by using the combined system of FeCl3 with Cl2CHOCH3. This unique cooperative system offered a new and efficient approach to biologically important xanthone and chromone derivatives with regioselectivity. Examples were reported, and control experiments were carried out to examine the effect of the benzyl esters and Cl2CHOCH3.

  通过使用FeCl3和Cl2CHOCH3的联合体系，发展了酯的直接分子内酰基化反应。该独特的协同体系为生物重要的黄酮和香豆素衍生物提供了一种新的高效方法，并具有区域选择性。报告了相关例子，并进行了对照实验，以检查苄基酯和Cl2CHOCH3的影响。