1-(4-bromophenyl)-2,2-diphenylethan-1-one | 1259024-98-0

• 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-(4-bromophenyl)-2,2-diphenylethan-1-one
• 英文别名: 1-(4-bromophenyl)-2,2-diphenylethanone；1-(4-Bromophenyl)-2,2-diphenylethanone
• CAS: 1259024-98-0
• 化学式: C₂₀H₁₅BrO
• 分子量: 351.242
• InChiKey: UAMLCRAOBYIYLZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.6
• 重原子数：
  22
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.05
• 拓扑面积：
  17.1
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为产物：
  描述：

  对溴苯甲醛 、 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91%的产率得到1-(4-bromophenyl)-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

• 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。
• Decarboxylative 1,2-rearrangement of cyclic carbonates promoted by Lewis acid
  作者：Yoichi Dokai、Kodai Saito、Tohru Yamada

  DOI：10.1039/d2cc03024a

  日期：——

  A Lewis acid-mediated decarboxylative 1,2-rearrangement reaction of cyclic carbonates was developed. The selectivity of the migration of cyclic carbonates was opposite to that of the corresponding 1,2-diols under the same reaction conditions.

  一种利用Lewis酸介导的环状碳酸酯的脱羧基1,2重排反应被开发出来。在相同的反应条件下，环状碳酸酯的迁移选择性与相应的1,2-二醇相反。
• 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.