3-(diphenylmethyl)-2,5-dimethylfuran

• 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-(diphenylmethyl)-2,5-dimethylfuran
• 英文别名: 3-benzhydryl-2,5-dimethylfuran
• 化学式: C₁₉H₁₈O
• 分子量: 262.351
• InChiKey: ZCVFMTHZSGGOOU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.2
• 重原子数：
  20
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.16
• 拓扑面积：
  13.1
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为产物：
  描述：

  二苯甲酮 在 sodium tetrahydroborate 、 [Cp*Ir(SnCl₃)2{SnCl₂(H₂O)2}] 、 sodium hydroxide 作用下， 以 甲醇 、 1,2-二氯乙烷 为溶剂， 生成 3-(diphenylmethyl)-2,5-dimethylfuran
  参考文献：
  名称：

  π-活化醇与碳和杂原子亲核试剂的多金属Ir-Sn 3催化取代反应

  摘要：

  已经证明了多金属Ir–Sn 3络合物的π活化醇的原子经济和催化取代反应。从[Cp ∗ IrCl 2 ] 2和SnCl 2之间的反应可以轻松合成多金属Ir-Sn 3络合物。在低至1 mol％的催化剂存在下，已使用碳将三种不同类型的π-活化醇，即苄基，烯丙基和炔丙基醇成功地转化为烷基化产物（芳烃，杂芳烃，烯丙基三甲基硅烷和1,3 （二羰基），氮（磺酰胺），氧（醇）和硫（硫醇）亲核试剂的收率非常高。Hammett相关性研究提出了一种亲电机理。

  DOI：

  10.1016/j.tet.2012.10.086

文献信息

• Efficient and selective alkylation of arenes and heteroarenes with benzyl and allyl ethers using a Ir/Sn bimetallic catalyst
  作者：Susmita Podder、Sujit Roy

  DOI：10.1016/j.tet.2007.06.068

  日期：2007.9

  A high-valent heterobimetallic catalyst namely [Ir2(COD)2(SnCl3)2(Cl)2(μ-Cl)2] (5 mol %), or dual catalyst system of [Ir(COD)Cl]2 (1 mol %) and SnCl4 (4 mol %), promotes the benzylation or allylation of arenes and heteroarenes using ethers as the alkylating agents. An electrophilic mechanism is proposed from a Hammett correlation.

  一种高价杂双金属催化剂，即[Ir 2（COD）2（SnCl 3）2（Cl）2（μ-Cl）2 ]（5 mol％），或[Ir（COD）Cl] 2（使用醚作为烷基化剂，1摩尔％）和SnCl 4（4摩尔％）促进芳烃和杂芳烃的苄基化或烯丙基化。由哈米特相关性提出了一种亲电机理。
• CuBr2-catalyzed alkylation of furans with benzyl alcohols and benzaldehydes. Domino reactions including this alkylation as a key step
  作者：Anton S. Makarov、Anna E. Kekhvaeva、Christopher J.J. Hall、Daniel R. Price、Igor V. Trushkov、Maxim G. Uchuskin

  DOI：10.1016/j.tet.2017.10.054

  日期：2017.12

  CuBr2-catalyzed alkylation of furans with a broad scope of benzyl alcohols and benzaldehydes is reported. Reaction proceeds efficiently under mild reaction conditions requiring no inert atmosphere or other precautions. Moreover, it is shown that CuBr2 catalyzes domino reactions of furans with benzyl alcohols or benzaldehydes bearing a nucleophilic moiety in the ortho-position. These protocols offer a

  据报道，CuBr 2催化的呋喃与范围广泛的苄醇和苯甲醛的烷基化。反应在温和的反应条件下有效进行，不需要惰性气氛或其他预防措施。此外，表明CuBr 2催化呋喃与在邻位带有亲核部分的苯甲醇或苯甲醛的多米诺反应。这些协议为从易于获得的呋喃中密集取代的杂环基序提供了一种实用的方法。
• 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.
• Dual-Reagent Catalysis within Ir−Sn Domain:  Highly Selective Alkylation of Arenes and Heteroarenes with Aromatic Aldehydes
  作者：Susmita Podder、Joyanta Choudhury、Ujjal Kanti Roy、Sujit Roy

  DOI：10.1021/jo062633n

  日期：2007.4.1

  Reactions of arenes and heteroarenes with aromatic aldehydes proceeded smoothly in the presence of a catalytic combination of [Ir(COD)Cl](2)-SnCl4 to afford the corresponding triarylmethane derivatives (TRAMs) in high yields. This 100% TRAM selective transformation is clean and eliminates the use of acid systems.