2-(4-nitrophenyl)-2-phenylacetaldehyde | 1070672-49-9

• 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-nitrophenyl)-2-phenylacetaldehyde
• CAS: 1070672-49-9
• 化学式: C₁₄H₁₁NO₃
• 分子量: 241.246
• InChiKey: ZSXMGKQRUFFECM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  18
• 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：
  62.9
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  trans-2-(4-nitrophenyl)-3-phenyloxirane 在 copper(II) tetrafluroborate hexahydrate 作用下， 以 二氯甲烷 为溶剂， 反应 6.0h， 以10%的产率得到2-(4-nitrophenyl)-2-phenylacetaldehyde
  参考文献：
  名称：

  四氟硼酸铜（II）促进环氧化物的Meinwald重排反应

  摘要：

  在催化量的四氟硼酸铜（II）的存在下，环氧树脂会进行高效的Meinwald重排，从而以高收率和优异的选择性得到羰基化合物。该试剂的低毒性和易处理性使其成为经常使用的更具腐蚀性或成本较高的路易斯酸的诱人替代品。

  DOI：

  10.1016/j.tet.2010.08.078

文献信息

• Inhibitors of Histone Deacetylase
  申请人：Tessier Pierre

  公开号：US20090181943A1

  公开（公告）日：2009-07-16

  This invention relates to compounds for the inhibition of histone deacetylase. More particularly, the invention provides for compounds of formula compounds of the Formula (I) and N-oxides, hydrates, solvates, pharmaceutically acceptable salts, prodrugs and complexes thereof, and racemic and scalemic mixtures, diastereomers and enantiomers thereof, wherein groups L, M, X and Y are as defined herein.

  该发明涉及用于抑制组蛋白去乙酰化酶的化合物。更具体地说，该发明提供了公式(I)化合物及其N-氧化物、水合物、溶剂物、药学上可接受的盐、前药和复合物，以及它们的外消旋和内消旋混合物、对映异构体，其中L、M、X和Y基团如本文所定义。
• 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.
• US9096565B2
  申请人：——

  公开号：US9096565B2

  公开（公告）日：2015-08-04
• [EN] INHIBITORS OF HISTONE DEACETYLASE<br/>[FR] INHIBITEURS D'HISTONE DÉACÉTYLASE
  申请人：METHYLGENE INC

  公开号：WO2008122115A1

  公开（公告）日：2008-10-16

  [EN] This invention relates to compounds for the inhibition of histone deacetylase. More particularly, the invention provides for compounds of formula compounds of the Formula (I) and N-oxides, hydrates, solvates, pharmaceutically acceptable salts, prodrugs and complexes thereof, and racemic and scalemic mixtures, diastereomers and enantiomers thereof, wherein groups L, M, X and Y are as defined herein.
  [FR] L'invention concerne des composés permettant d'inhiber l'histone déacétylase. Plus particulièrement, l'invention concerne des composés représentés par la formule (I) et, N-oxydes, des hydrates, des solvates et des sels pharmaceutiquement acceptables, des promédicaments et des complexes de ces composés, ainsi que des mélanges racémiques et scalémiques, des diastéréomères et des énantiomères de ceux-ci, les groupes L, M, X et Y étant tels que définis dans la description.
• Copper(II) tetrafluroborate-promoted Meinwald rearrangement reactions of epoxides
  作者：Mathew W.C. Robinson、Kathryn S. Pillinger、Ian Mabbett、David A. Timms、Andrew E. Graham

  DOI：10.1016/j.tet.2010.08.078

  日期：2010.10

  Epoxides undergo a highly efficient Meinwald rearrangement in the presence of catalytic quantities of copper(II) tetrafluoroborate to give carbonyl compounds in high yields and with excellent selectivity. The low toxicity and ease of handling of this reagent make it an attractive alternative to the more corrosive or costly Lewis acids frequently employed.

  在催化量的四氟硼酸铜（II）的存在下，环氧树脂会进行高效的Meinwald重排，从而以高收率和优异的选择性得到羰基化合物。该试剂的低毒性和易处理性使其成为经常使用的更具腐蚀性或成本较高的路易斯酸的诱人替代品。