3-benzhydrylthiophene | 1448794-49-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 3-benzhydrylthiophene
• CAS: 1448794-49-7
• 化学式: C₁₇H₁₄S
• 分子量: 250.364
• InChiKey: MIGFURCZJKHNFW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5
• 重原子数：
  18
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.06
• 拓扑面积：
  28.2
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为产物：
  描述：

  苄基苯基砜 在 bis(η3-allyl-μ-chloropalladium(II)) 、 potassium tert-butylate 、 sodium hydroxide 、 1,3-双-(2,6-二异丙基苯基)咪唑鎓氯化物 、 tri tert-butylphosphoniumtetrafluoroborate 作用下， 以 1,4-二氧六环 、 水 为溶剂， 反应 24.0h， 生成 3-benzhydrylthiophene
  参考文献：
  名称：

  钯催化甲基苯砜的顺序芳基化模块合成三芳基甲烷

  摘要：

  三芳基甲烷是材料，传感和药物中的重要结构，已从甲基苯基砜作为廉价且易于获得的模板开始合成。三个芳基是通过两个连续的钯催化的安装在C  ħ芳基化反应，接着是脱磺arylative。该方法使用易于获得的卤代芳烃和芳基硼酸为多取代的三芳基甲烷提供了一种新的合成方法，对于制备未开发的基于三芳基甲烷的材料和药物也很有价值。

  DOI：

  10.1002/anie.201307019

文献信息

• Synthesis of Triarylmethanes via Palladium-Catalyzed Suzuki–Miyaura Reactions of Diarylmethyl Esters
  作者：Amira H. Dardir、Irene Casademont-Reig、David Balcells、Jonathan D. Ellefsen、Matthew R. Espinosa、Nilay Hazari、Nicholas E. Smith

  DOI：10.1021/acs.organomet.1c00085

  日期：2021.7.26

  compatible with systems for diarylmethyl ester coupling. Furthermore, the reaction can be performed stereospecifically to generate stereoinverted products. On the basis of DFT calculations, it is proposed that the oxidative addition of the diarylmethyl 2,3,4,5,6-pentafluorobenzoate substrate occurs via an SN2 pathway, which results in the inverted products. Mechanistic studies indicate that oxidative addition

  描述了通过 Pd 催化的 2,3,4,5,6-五氟苯甲酸二芳基甲酯和芳基硼酸之间的 Suzuki-Miyaura 反应合成三芳基甲烷。该系统在温和的条件下运行，具有广泛的底物范围，包括不包含扩展芳族取代基的二苯甲醇衍生物的偶联。这一点很重要，因为这些底物会导致药物中普遍存在的三芳基甲烷产物类型，而这些底物以前并不与二芳基甲酯偶联系统兼容。此外，该反应可以立体特异性地进行以产生立体反转产物。在 DFT 计算的基础上，提出 2,3,4,5,6-五氟苯甲酸二芳基甲酯底物的氧化加成是通过 S N2 通路，从而产生倒置产物。机理研究表明，将 2,3,4,5,6-五氟苯甲酸二芳基甲酯底物氧化加成到 (IPr)Pd(0) 会导致 O-C(苄基) 键的选择性断裂，部分原因是稳定的 η苄基配体与 Pd 之间的3 -相互作用。这与先前描述的涉及苯基酯的 Pd 催化的 Suzuki-Miyaura 反应形成对比，后者涉及
• Synthesis of Triarylmethanes via Palladium-Catalyzed Suzuki Coupling of Trimethylammonium Salts and Arylboronic Acids
  作者：Zhenming Zhang、Hui Wang、Nianli Qiu、Yujing Kong、Wenjuan Zeng、Yongquan Zhang、Junfeng Zhao

  DOI：10.1021/acs.joc.8b00965

  日期：2018.8.3

  An efficient palladium-catalyzed Suzuki coupling of 1,1-diarylmethyl-trimethylammonium triflates with arylboronic acids is reported. This reaction offers a novel approach to triarylmethane derivatives in good to excellent yields with the palladium-catalyzed C–N bond cleavage as the key feature. Broad substrate scope regarding both reaction partners are observed. Moreover, reactive functional groups

  报道了1，1-二芳基甲基-三甲基铵三氟甲磺酸与芳基硼酸的有效钯催化的Suzuki偶联。该反应提供了一种新颖的方法，以钯催化的C–N键断裂为关键特征，可以以良好或优异的收率获得三芳基甲烷衍生物。观察到关于两种反应伙伴的广泛的底物范围。此外，在该转化中保守了诸如乙烯基和甲酰基的反应性官能团。
• Arylative Desulfonation of Diarylmethyl Phenyl Sulfone with Arenes Catalyzed by Scandium Triflate
  作者：Masakazu Nambo、Zachary T. Ariki、Daniel Canseco-Gonzalez、D. Dawson Beattie、Cathleen M. Crudden

  DOI：10.1021/acs.orglett.6b00744

  日期：2016.5.20

  A scandium-triflate-catalyzed arylative desulfonation of diarylmethyl phenyl sulfones with arenes and heteroarenes was established. A variety of both sulfone and arene substrates were reacted to afford symmetric and nonsymmetric triarylmethanes in good yields. Further transformations of the resulting triarylmethanes and application to the concise synthesis of a bactericidal agent analogue were also demonstrated.
• Benzylation of arenes with benzyl halides synergistically promoted by in situ generated superacid boron trifluoride monohydrate and tetrahaloboric acid
  作者：Ruofeng Huang、Xiaohui Zhang、Jing Pan、Jiaqiang Li、Hang Shen、Xuege Ling、Yan Xiong

  DOI：10.1016/j.tet.2015.01.037

  日期：2015.3

  To examine the assembly methodology of diarylmethanes, a benzylation of (hetero)arenes with benzyl halides has been developed and various diarylmethanes were furnished with yields of up to 98% and regioselectivities of up to >99%. The complexation of the by-product halogen hydride with BF3 center dot OEt2 generated the Bronsted acid BF3 center dot HX (HBF3X, X=Cl or Br) in situ to synergistically promote the benzylation. (C) 2015 Elsevier Ltd. All rights reserved.
• Modular Synthesis of Triarylmethanes through Palladium-Catalyzed Sequential Arylation of Methyl Phenyl Sulfone
  作者：Masakazu Nambo、Cathleen M. Crudden

  DOI：10.1002/anie.201307019

  日期：2014.1.13

  Triarylmethanes, which are valuable structures in materials, sensing and pharmaceuticals, have been synthesized starting from methyl phenyl sulfone as an inexpensive and readily available template. The three aryl groups were installed through two sequential palladium‐catalyzed CH arylation reactions, followed by an arylative desulfonation. This method provides a new synthetic approach to multisubstituted

  三芳基甲烷是材料，传感和药物中的重要结构，已从甲基苯基砜作为廉价且易于获得的模板开始合成。三个芳基是通过两个连续的钯催化的安装在C  ħ芳基化反应，接着是脱磺arylative。该方法使用易于获得的卤代芳烃和芳基硼酸为多取代的三芳基甲烷提供了一种新的合成方法，对于制备未开发的基于三芳基甲烷的材料和药物也很有价值。