5,5'-(phenylmethylene)bis(2-methylthiophene) | 126045-46-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 噻吩类
• 英文名称: 5,5'-(phenylmethylene)bis(2-methylthiophene)
• 英文别名: Thiophene, 2,2'-(phenylmethylene)bis[5-methyl-；2-methyl-5-[(5-methylthiophen-2-yl)-phenylmethyl]thiophene
• CAS: 126045-46-3
• 化学式: C₁₇H₁₆S₂
• 分子量: 284.446
• InChiKey: QNMVACRLWXFDIH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.5
• 重原子数：
  19
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  56.5
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  2-methyl-5-[(5-methylfuran-2-yl)(phenyl)methyl]furan 在 盐酸 、 硫化氢 作用下， 以 丙醇 为溶剂， 以41%的产率得到5,5'-(phenylmethylene)bis(2-methylthiophene)
  参考文献：
  名称：

  Conversion of di(furyl-2)alkyl and di(furyl-2)arylmethanes to the thiophene analogs

  摘要：

  DOI：

  10.1007/bf00479603

文献信息

• Iron-Catalyzed Arylation of Aromatic Ketones and Aldehydes Mediated by Organosilanes
  作者：Risto Savela、Marcin Majewski、Reko Leino

  DOI：10.1002/ejoc.201402023

  日期：2014.7

  arylation of aromatic carbonyl compounds is reported. The use of 4 % FeCl3 or Fe(acac)3 as the catalyst, in combination with a slight excess of chlorotrimethylsilane and triethylsilane, chlorination of benzylic ketones and aldehydes with subsequent Friedel–Crafts alkylation of arenes is achieved. Although the method is limited by the general constraints associated with Friedel–Crafts alkylation reactions

  报道了一种简单有效的铁催化芳族羰基化合物芳基化方法。使用 4% FeCl3 或 Fe(acac)3 作为催化剂，结合略微过量的三甲基氯硅烷和三乙基硅烷，实现苄基酮和醛的氯化，随后芳烃的 Friedel-Crafts 烷基化。尽管该方法受到与 Friedel-Crafts 烷基化反应相关的一般约束的限制，但可以设想在药物中间体等方面的稳健应用。
• Di- and triheteroarylalkanes via self-condensation and intramolecular Friedel–Crafts type reaction of heteroaryl alcohols
  作者：Seema Dhiman、S. S. V. Ramasastry

  DOI：10.1039/c3ob41945b

  日期：——

  diheteroarylmethanes and 1,3-diheteroarylpropenes has been developed via Yb(III)-catalyzed sequential self-condensation of 2-furfuryl (or 2-thienyl or 3-indolyl) alcohols followed by intramolecular Friedel–Crafts type reaction and elimination of an aldehyde. This method offers a powerful entry and a potential alternative to the traditional synthesis of diheteroarylalkanes, which are precursors to the synthesis

  通过Yb（III）催化2-糠基（或2-噻吩基或3-吲哚基）醇的顺序自缩合反应，然后进行分子内Friedel-Crafts型反应，开发了一种有效的合成方法，用于二杂芳基甲烷和1,3-二杂芳基丙烯。消除醛。该方法为传统的二杂芳基烷烃的合成提供了有力的途径和潜在的替代方法，后者是几种有趣的杂芳基化合物的合成的前体，更重要的是生物燃料的合成。
• Practical Synthesis of Triaryl- and Triheteroarylmethanes by Reaction of Aldehydes and Activated Arenes Promoted by Gold(III) Chloride
  作者：Vijay Nair、K. G. Abhilash、N. Vidya

  DOI：10.1021/ol052423h

  日期：2005.12.1

  [reaction: see text] Electron-rich arenes condense efficiently with various aldehydes under the influence of AuCl3, thus opening up a practical route to triarylmethanes, which have important applications. The mild conditions employed are especially noteworthy.

  [反应：参见正文]在AuCl3的影响下，富电子芳烃与各种醛类有效地缩合，从而开辟了一条实用的生产三芳基甲烷的途径，这具有重要的应用前景。使用的温和条件尤其值得注意。
• Sulfonated Tetraphenylethylene-Based Hypercrosslinked Polymer as a Heterogeneous Catalyst for the Synthesis of Symmetrical Triarylmethanes via a Dual C–C Bond-Cleaving Path
  作者：Gitumoni Kalita、Namrata Deka、Dipankar Paul、Gitish K. Dutta、Paresh Nath Chatterjee、Loknath Thapa

  DOI：10.1055/a-1277-3995

  日期：2021.2

  A sulfonic acid functionalized tetraphenylethylene-based hypercrosslinked polymer (THP-SO3H) with a well-developed porous network and accessible sulfonic acid sites was synthesized and characterized by different analytical techniques. The catalytic prowess of the synthesized material THP-SO3H was investigated in a challenging dual C–C bond-breaking reaction for the synthesis of symmetrical triarylmethanes (TRAMs) in high yield. The scope of the developed metal-free method was also explored with a wide variety of substrates. The organocatalyst can be easily recovered by filtration and reused up to five consecutive cycles without substantial loss in its catalytic efficacy.

  标题：摘要 一种含磺酸基团的四苯基乙烯基高交联聚合物（THP-SO3H）具有良好发达的多孔网络和可访问的磺酸基团，通过不同的分析技术合成并表征。合成材料THP-SO3H的催化能力在一种具有挑战性的双C-C键断裂反应中得到研究，用于合成高收率的对称三芳基甲烷（TRAMs）。还探索了开发的无金属方法在各种底物上的适用范围。这种有机催化剂可以通过过滤轻松回收并在五个连续循环中重复使用，而其催化效能几乎没有明显损失。
• RuCl3·3H2O Catalyzed Reactions: Facile Synthesis of Bis(indolyl)methanes under Mild Conditions
  作者：Hong-En Qu、Chen Xiao、Ning Wang、Kai-Hui Yu、Qiao-Sheng Hu、Liang-Xian Liu

  DOI：10.3390/molecules16053855

  日期：——

  RuCl3·3H2O was found to be an effective catalyst for reactions of indoles, 2-methylthiophene, and 2-methylfuran with aldehydes to afford the corresponding bis(indolyl)methanes, bis(thienyl)methanes, and bis(fur-2-yl)methanes in moderate to excellent yields. Experimental results indicated that mono(indolyl)methanol is not the reaction intermediate under these reaction conditions.

  实验结果表明，三水合氯化钌(RuCl3·3H2O)是一种有效的催化剂，可用于吲哚、2-甲基噻吩和2-甲基呋喃与醛反应，以中等至优异的产率得到相应的双(吲哚基)甲烷、双(噻吩基)甲烷和双(呋喃-2-基)甲烷。这些反应条件下，单(吲哚基)甲醇不是反应中间体。