1-(3-methoxyphenyl)-2,2-diphenylethan-1-one | 68181-90-8

• 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: 1-(3-methoxyphenyl)-2,2-diphenylethan-1-one
• 英文别名: 1-(3-methoxyphenyl)-2,2-diphenylethanone；1-(3-Methoxyphenyl)-2,2-diphenylethanone
• CAS: 68181-90-8
• 化学式: C₂₁H₁₈O₂
• 分子量: 302.373
• InChiKey: WKDJFZFMHJPQEA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.9
• 重原子数：
  23
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.1
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  3-甲氧基苯甲醛 、 二苯基溴甲烷 在 3-mesityl-5,6,7,8-tetrahydro-4H-cyclohepta[d]thiazol-3-ium perchlorate 、 caesium carbonate 作用下， 以 四氢呋喃 为溶剂， 反应 3.0h， 以79%的产率得到1-(3-methoxyphenyl)-2,2-diphenylethan-1-one
  参考文献：
  名称：

  N-Heterocyclic Carbene-Catalyzed Cross-Coupling of Aromatic Aldehydes with Activated Alkyl Halides

  摘要：

  N-Heterocyclic carbene-catalyzed umpolung of aldehydes followed by their interception with diarylbromomethanes has been reported. This conceptually novel transition-metal-free cross-coupling of aldehydes with alkyl halides works well at low catalyst loadings and under mild reaction conditions leading to the formation of diaryl acetophenone derivatives in good yields. In addition, a-halo ketones and esters can also be used, as aldehyde reaction partners.

  DOI：

  10.1021/ol102626p

文献信息

• Aqueous α-Arylation of Mono- and Diarylethanone Enolates at Low Catalyst Loading
  作者：Iratxe Astarloa、Raul SanMartin、María Teresa Herrero、Esther Domínguez

  DOI：10.1002/adsc.201701596

  日期：2018.4.17

  Acetophenone and deoxybenzoin derivatives are selectively α‐arylated using a combination of very small amounts of palladium acetate and diphenylphosphine oxide as catalyst system and water as the only solvent. Target di‐ and triarylethanones are isolated virtually free of metal residues, and the reaction is amenable to gram‐scale. A mechanistic proposal based on TEM images, poisoning experiments, kinetic

  苯乙酮和脱氧安息香衍生物通过使用极少量的乙酸钯和二苯膦氧化物作为催化剂体系，而水作为唯一溶剂，选择性地进行α-芳基化。分离出的目标二-和三芳基酮几乎不含金属残留物，反应量可达到克级。还提供了基于TEM图像，中毒实验，动力学图和ESI-MS光谱的机械方案。
• Reaction of Selenium Dioxide with Aromatic Ketones in the Presence of Boron Triflouride Etherate: A Protocol for the Synthesis of Triarylethanones
  作者：Badaker M. Laloo、Hormi Mecadon、Md. Rumum Rohman、Iadeishisha Kharbangar、Icydora Kharkongor、Mantu Rajbangshi、Rishanlang Nongkhlaw、Bekington Myrboh

  DOI：10.1021/jo201985n

  日期：2012.1.6

  An efficient regioselective protocol for the C–C bond formation by the unexpected α,α-diarylation of aromatic ketones with unactivated arenes in the presence of selenium dioxide and boron trifluoride etherate has been developed. The generality and functional tolerance of this protocol is demonstrated by the synthesis of a series of triarylethanones.

  在二氧化硒和三氟化硼醚化物存在下，通过未活化的芳烃与未活化的芳烃进行意想不到的α，α-二芳基化反应，形成有效的C-C键区域选择方案。该协议的一般性和功能耐受性由一系列三芳基酮的合成证明。
• N-Heterocyclic Carbene-Catalyzed Cross-Coupling of Aromatic Aldehydes with Activated Alkyl Halides
  作者：Mohan Padmanaban、Akkattu T. Biju、Frank Glorius

  DOI：10.1021/ol102626p

  日期：2011.1.7

  N-Heterocyclic carbene-catalyzed umpolung of aldehydes followed by their interception with diarylbromomethanes has been reported. This conceptually novel transition-metal-free cross-coupling of aldehydes with alkyl halides works well at low catalyst loadings and under mild reaction conditions leading to the formation of diaryl acetophenone derivatives in good yields. In addition, a-halo ketones and esters can also be used, as aldehyde reaction partners.