2-(4-cyanophenyl)-2-phenyl acetaldehyde | 931426-36-7

• 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: 2-(4-cyanophenyl)-2-phenyl acetaldehyde
• 英文别名: 2-(4-cyanophenyl)-2-phenylacetaldehyde；4-(2-oxo-1-phenylethyl)-benzonitrile；4-(2-Oxo-1-phenylethyl)benzonitrile；4-(2-oxo-1-phenylethyl)benzonitrile
• CAS: 931426-36-7
• 化学式: C₁₅H₁₁NO
• 分子量: 221.258
• InChiKey: SHCKHWGARBXWMX-UHFFFAOYSA-N

物化性质

• 沸点：
  388.8±30.0 °C(Predicted)
• 密度：
  1.15±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  17
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  40.9
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  4-溴苯腈 、 苯乙醛 在 palladium diacetate 、 2'-hydroxy-2-di-cyclohexylphosphinobiphenyl-4'-sulfonic acid sodium t-butanolate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 14.75h， 以65%的产率得到2-(4-cyanophenyl)-2-phenyl acetaldehyde
  参考文献：
  名称：

  Process for Preparing 2-Arylcarbonyl Compounds, 2-Aryl Esters and 2-Arylnitriles and their Heteroaromatic Analogues

  摘要：

  通过在存在Brönsted碱和包含a.)过渡金属、配合物、盐或来自V、Mn、Fe、Co、Ni、Rh、Pd、Ir、Pt组的该过渡金属化合物的催化剂或前催化剂的情况下，使用含有至少一种磺化膦配体的溶剂或溶剂混合物，通过交叉偶联烯醇化的羰基化合物、腈或它们的类似物与取代芳基或杂环芳基化合物的方法。

  公开号：

  US20080221350A1

文献信息

• Catalytic, regioselective, and green methods for rearrangement of 1,2-diaryl epoxides to carbonyl compounds employing metallic triflates, Brønsted-acidic ionic liquids (ILs), and IL/microwave; experimental and computational substituent effect study on aryl versus hydrogen migration
  作者：Arezu Jamalian、Benjamin Rathman、Gabriela L. Borosky、Kenneth K. Laali

  DOI：10.1016/j.apcata.2014.08.009

  日期：2014.9

  The Lewis-acid catalyzed rearrangement of parent trans-stilbene oxide 1 was studied with M(OTf)(3)/DCM and M(OTf)(3)/[BMIM][BF4] (M = Bi, Al, Ga, Sc, and Yb; [BMIM] = butylmethylimidazolium) and Zn(NTf2)(2), and with Bi(OTf)(3)/[BMIM][X] (X = NTf2, OTf, PF6, and BF4), employing 5 mol% of catalyst. Selective formation of 2,2-dipheylacetaldehyde 2 (phenyl migration product) was observed in all cases, with Bi(OTf)(3) proving most efficient. The rearrangement of I was also effected in [BMIM][X] (X = NTf2, OTf, PF6, and BF4) without an added catalyst under microwave MW irradiation, and X = PF6 gave the highest yield and selectivity. Efficient and selective rearrangement of 1-2 was also observed with 0.1-0.3 equiv. of [BMIM(SO3H)][OTf] in DCM and in [BMIM][X]. A substituent effect study was performed with a series of singly substituted 1,2-diphenyl oxiranes (with X = OMe, Me, F, CN, and NO2) with 5 mol% Bi(OTf)(3) in DCM and in [BMIM][NTf2]. Notable formation of ketones was observed with the NO2 and CN derivatives. Competing formation of ketones was also observed in [BMIM][PF6] under MW and under Bronsted acid catalysis with [BMIM(SO3H)][OTf] in DCM and in [BMIM][NTf2]. The aryl versus H migration was studied computationally by OFT and MP2 methods and by including solvation effects (IEFPCM). (C) 2014 Elsevier B.V. All rights reserved.
• Process for Preparing 2-Arylcarbonyl Compounds, 2-Aryl Esters and 2-Arylnitriles and their Heteroaromatic Analogues
  申请人：Meudt Andreas

  公开号：US20080221350A1

  公开（公告）日：2008-09-11

  Process for preparing compounds by cross-coupling of enolizable carbonyl compounds, nitriles or their analogues with substituted aryl or heteroaryl compounds in the presence of a Brönsted base and of a catalyst or precatalyst containing a.) a transition metal, a complex, a salt or a compound of this transition metal from the group V, Mn, Fe, Co, Ni, Rh, Pd, Ir, Pt) and b.) at least one sulphonated phosphane ligand in a solvent or solvent mixture.

  通过在存在Brönsted碱和包含a.)过渡金属、配合物、盐或来自V、Mn、Fe、Co、Ni、Rh、Pd、Ir、Pt组的该过渡金属化合物的催化剂或前催化剂的情况下，使用含有至少一种磺化膦配体的溶剂或溶剂混合物，通过交叉偶联烯醇化的羰基化合物、腈或它们的类似物与取代芳基或杂环芳基化合物的方法。