1-(4-bromophenyl)-2-(tert-butylimino)ethanone | 1256291-73-2

• 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: 1-(4-bromophenyl)-2-(tert-butylimino)ethanone
• 英文别名: 1-(4-Bromophenyl)-2-tert-butyliminoethanone；1-(4-bromophenyl)-2-tert-butyliminoethanone
• CAS: 1256291-73-2
• 化学式: C₁₂H₁₄BrNO
• 分子量: 268.153
• InChiKey: CBUDYNMQOCVQLM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  15
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  29.4
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  1-(4-bromophenyl)-2-(tert-butylimino)ethanone 在 sodium tetrahydroborate 、 cesium fluoride 作用下， 以 乙醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 12.0h， 生成
  参考文献：
  名称：

  （二氟甲基）三甲基硅烷的亲核加成反应到选定的α-亚氨基酮和芳基二酮

  摘要：

  在引发剂（例如叔丁醇钾或铯）存在下，研究了将二氟甲基三甲基硅烷（CHF 2 SiMe 3）化学选择性加成到芳基乙二醛衍生的α-亚氨基酮的羰基键上，以及选定的二芳基1,2-二酮。氟化物。随后用硼氢化钠还原获得的α-亚氨基醇和α-羟基酮，分别以中等至良好的收率得到了预期的2-氨基1-（二氟甲基）醇和（二氟甲基）-1，2-二醇。对于α-（二氟甲基）-α-羟基酮的还原，观察到较高的de值。

  DOI：

  10.1016/j.tetlet.2015.06.025
• 作为产物：
  描述：

  4-溴苯基水合乙二醛 、 叔丁胺 以 甲苯 为溶剂， 反应 3.0h， 以87%的产率得到1-(4-bromophenyl)-2-(tert-butylimino)ethanone
  参考文献：
  名称：

  Asymmetric synthesis of β-amino alcohols by the transfer hydrogenation of α-keto imines

  摘要：

  The asymmetric transfer hydrogenation of representative aryl and benzofuranyl 2-tert-butylaminoethanones with formic acid-triethylamine, catalyzed by RhCl[(R,R)-T5DPEN](C5Me5), produced the corresponding beta-tert-butylamino alcohols in 97-99% ee. A short asymmetric synthesis of (R)-bufuralol, a potent beta-adrenergic receptor antagonist, is described. This approach to beta-amino alcohols from ketones circumvents the halogenation-reduction-amination sequence. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2010.07.004

文献信息

• Chemoselective trifluoromethylation of the C N group of α-iminoketones derived from arylglyoxals
  作者：Emilia Obijalska、Marcin K. Kowalski、Grzegorz Mlostoń、Anthony Linden、Heinz Heimgartner

  DOI：10.1016/j.jfluchem.2014.09.002

  日期：2014.12

  Chemoselective addition of (trifluoromethyl)trimethylsilane to the C=N group of N-(tert-butyl)-alpha-iminoketones in the presence of a fluoride ion as a catalyst was achieved under acidic conditions. Subsequent diastereoselective reductions of the obtained alpha-amino-alpha-(trifluoromethyl)ketones led to beta-amino-beta-(trifluoromethyl) alcohols in very good yields and high diastereoselectivities. Different reducing agents were tested; the reduction performed with LiAlH4 and Raney-Ni, respectively, afforded the desired diastereoisomers in a reversed ratio. (C) 2014 Elsevier B.V. All rights reserved.
• Asymmetric synthesis of β-amino alcohols by the transfer hydrogenation of α-keto imines
  作者：Agnieszka Tafelska-Kaczmarek、Andrzej Prewysz-Kwinto、Krzysztof Skowerski、Katarzyna Pietrasiak、Anna Kozakiewicz、Marek Zaidlewicz

  DOI：10.1016/j.tetasy.2010.07.004

  日期：2010.9

  The asymmetric transfer hydrogenation of representative aryl and benzofuranyl 2-tert-butylaminoethanones with formic acid-triethylamine, catalyzed by RhCl[(R,R)-T5DPEN](C5Me5), produced the corresponding beta-tert-butylamino alcohols in 97-99% ee. A short asymmetric synthesis of (R)-bufuralol, a potent beta-adrenergic receptor antagonist, is described. This approach to beta-amino alcohols from ketones circumvents the halogenation-reduction-amination sequence. (C) 2010 Elsevier Ltd. All rights reserved.
• Nucleophilic addition of (difluoromethyl)trimethylsilane to selected α-imino ketones and aryl diketones
  作者：Emilia Obijalska、Greta Utecht、Marcin K. Kowalski、Grzegorz Mlostoń、Michał Rachwalski

  DOI：10.1016/j.tetlet.2015.06.025

  日期：2015.8

  addition of (difluoromethyl)trimethylsilane (CHF2SiMe3) to the carbonyl bond of aryl glyoxal derived α-imino ketones, and selected diaryl 1,2-diketones were studied in the presence of initiators, such as potassium tert-butoxide or caesium fluoride. Subsequent reduction of the obtained α-imino alcohols and α-hydroxy ketones with sodium borohydride gave the expected 2-amino 1-(difluoromethyl)alcohols and

  在引发剂（例如叔丁醇钾或铯）存在下，研究了将二氟甲基三甲基硅烷（CHF 2 SiMe 3）化学选择性加成到芳基乙二醛衍生的α-亚氨基酮的羰基键上，以及选定的二芳基1,2-二酮。氟化物。随后用硼氢化钠还原获得的α-亚氨基醇和α-羟基酮，分别以中等至良好的收率得到了预期的2-氨基1-（二氟甲基）醇和（二氟甲基）-1，2-二醇。对于α-（二氟甲基）-α-羟基酮的还原，观察到较高的de值。