6-methyl-1-methylene-2,3-diphenyl-1H-indene | 1217446-76-8

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 二苯乙烯类
• 英文名称: 6-methyl-1-methylene-2,3-diphenyl-1H-indene
• 英文别名: 5-Methyl-3-methylidene-1,2-diphenylindene；5-methyl-3-methylidene-1,2-diphenylindene
• CAS: 1217446-76-8
• 化学式: C₂₃H₁₈
• 分子量: 294.396
• InChiKey: TZQJUPMEAWBVMR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.5
• 重原子数：
  23
• 可旋转键数：
  2
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.04
• 拓扑面积：
  0
• 氢给体数：
  0
• 氢受体数：
  0

反应信息

• 作为产物：
  描述：

  二苯基乙炔 、 3'-甲基苯乙酮 在 [Ir(cod)₂]OTf 、 R-(+)-1,1'-联萘-2,2'-双二苯膦 作用下， 以 氯苯 为溶剂， 反应 24.0h， 以88%的产率得到6-methyl-1-methylene-2,3-diphenyl-1H-indene
  参考文献：
  名称：

  Sequential Catalytic Reactions for the Synthesis of Benzofulvenes Using an Iridium Complex with Dual Function

  摘要：

  阳离子铱络合物([Ir(cod)2]OTf + 外消旋-BINAP)高效催化了一系列邻位C-H键官能化、环化及脱水过程，从而简便地制备了1-亚甲基茚（苯并富烯）衍生物。该铱络合物作为催化剂，在芳基酮与炔烃的邻位C-H键烯丙基化反应中发挥作用，并在烯丙基化产物环化及后续脱水中作为Lewis酸催化剂。

  DOI：

  10.1055/s-0029-1218575

文献信息

• The Synthesis of Benzofulvenes through Palladium-Catalyzed Sequential Three-Component Reactions
  作者：Bo Zhou、Zhuo Wu、Weixin Qi、Xueliang Sun、Yanghui Zhang

  DOI：10.1002/adsc.201801141

  日期：2018.12.3

  An approach for the synthesis of benzofulvenes has been developed through palladium‐catalyzed sequential three‐component reactions. The reactions likely involve C,C‐palladacycles as the key intermediates. The palladacycles are generated through cascade reactions of aryl halides and alkynes, and then reacted with CH2Br2 to form benzofulvenes as the final products.

  通过钯催化的连续三组分反应，已经开发出一种苯并富烯的合成方法。反应可能涉及C，C- palladacycles作为关键中间体。Palladacycles是通过芳基卤化物和炔烃的级联反应生成的，然后与CH 2 Br 2反应形成苯并富勒烯作为最终产物。
• Diverse Strategies toward Indenol and Fulvene Derivatives: Rh-Catalyzed C−H Activation of Aryl Ketones Followed by Coupling with Internal Alkynes
  作者：Frederic W. Patureau、Tatiana Besset、Nadine Kuhl、Frank Glorius

  DOI：10.1021/ja110650m

  日期：2011.2.23

  The synthesis of indenols and fulvenes was achieved through Rh-catalyzed C-H bond activation of simple and diverse aryl ketone derivatives and subsequent coupling with internal alkynes. The process was found to involve either an α or γ dehydration step, depending on the substrate disposition and representing diverse pathways toward functionalized fulvenes.

  茚醇和富烯的合成是通过 Rh 催化的 CH 键活化简单多样的芳基酮衍生物并随后与内部炔烃偶联来实现的。发现该过程涉及 α 或 γ 脱水步骤，具体取决于底物配置并代表通往功能化富烯的多种途径。
• Lewis Acid Enhancement of Gold Catalytic Activity Through Counterion Coordination. Synthesis of Benzofulvenes from Progargylsilanes and Benzophenones
  作者：Sergio Fernández、Javier Santamaría、Alfredo Ballesteros

  DOI：10.1002/adsc.202200165

  日期：2022.3.30

  intermediates, such as enynes and silylbenzofulvenes, have been isolated. Different control experiments have been performed, indicating the participation of [LAu][NTf2AlCl3] complex as the true catalyst, and revealing a dramatic enhancement of the gold activity by coordination of the Lewis acid to the gold counterion.

  描述了一种简单、区域选择性和高产率的金催化苯并富烯合成方法，该合成方法由前炔丙基硅烷和二苯甲酮组成。最初，羰基化合物被甲硅烷基部分协同活化，对于环化步骤，金催化活性通过作为助催化剂的三氯化铝的参与明显增加。已经分离出几种机械中间体，例如烯炔和甲硅烷基苯并富烯。已经进行了不同的对照实验，表明 [LAu][NTf 2 AlCl 3 ] 配合物作为真正的催化剂参与，并揭示了路易斯酸与金抗衡离子的配位显着提高了金的活性。
• Sequential Catalytic Reactions for the Synthesis of Benzofulvenes Using an Iridium Complex with Dual Function
  作者：Takanori Shibata、Kyoji Tsuchikama、Mitsugu Kasagawa、Kohei Endo

  DOI：10.1055/s-0029-1218575

  日期：2010.1

  The cationic iridium complex ([Ir(cod)2]OTf + rac-­BINAP) efficiently catalyzed a sequential process of ortho-C-H bond functionalization, cyclization and dehydration, leading to a concise preparation of 1-methylene indene (benzofulvene) derivatives. The iridium complex operated as a catalyst in the ortho-C-H bond alkenylation of aryl ketones with alkynes and as a Lewis acid catalyst in the cyclization of the alkenylated product and the subsequent dehydration.

  阳离子铱络合物([Ir(cod)2]OTf + 外消旋-BINAP)高效催化了一系列邻位C-H键官能化、环化及脱水过程，从而简便地制备了1-亚甲基茚（苯并富烯）衍生物。该铱络合物作为催化剂，在芳基酮与炔烃的邻位C-H键烯丙基化反应中发挥作用，并在烯丙基化产物环化及后续脱水中作为Lewis酸催化剂。