2-(tert-butylimino)(4'-methoxyphenyl)ethanone | 1256291-74-3

• 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-(tert-butylimino)(4'-methoxyphenyl)ethanone
• 英文别名: 2-Tert-butylimino-1-(4-methoxyphenyl)ethanone；2-tert-butylimino-1-(4-methoxyphenyl)ethanone
• CAS: 1256291-74-3
• 化学式: C₁₃H₁₇NO₂
• 分子量: 219.283
• InChiKey: ARZYKGSFRJDSSR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  16
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  38.7
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2-(tert-butylimino)(4'-methoxyphenyl)ethanone 在 甲酸 、 RhCl[(R,R)-TsDPEN]Cp* 、 三乙胺 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 24.0h， 生成 (1S)-2-(tert-butylamino)-1-(4-methoxyphenyl)ethanol
  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
• 作为产物：
  描述：

  4-甲氧基苯甲酰甲醛水合物 、 叔丁胺 以 二氯甲烷 为溶剂， 生成 2-(tert-butylimino)(4'-methoxyphenyl)ethanone
  参考文献：
  名称：

  （三氟甲基）三甲基硅烷向衍生自芳基乙二醛的α-亚氨基酮的对映选择性加成

  摘要：

  在催化量的对映体纯的溴化铵，金鸡纳生物碱和K 2 CO 3的存在下，将（三氟甲基）三甲基硅烷化学选择性加成到芳基乙二醛的α-亚氨基酮上，生成O-甲硅烷基化的β-亚氨基醇。随后用NaBH 4还原这些产物，得到β-（N-烷基）氨基-α-三氟甲基醇，在最佳条件下，其ee值为30 – 71％。根据在手性溶剂化剂存在下记录的1 H或19 F NMR光谱确定最终产物的对映体过量。

  DOI：

  10.1016/j.tetlet.2013.02.093

文献信息

• 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。
• Reactions of α-imino ketones derived from arylglyoxals with (trifluoromethyl)trimethylsilane; a new route to β-amino-α-trifluoromethyl alcohols
  作者：Grzegorz Mloston、Emilia Obijalska、Agnieszka Tafelska-Kaczmarek、Marek Zaidlewicz

  DOI：10.1016/j.jfluchem.2010.07.012

  日期：2010.12

  The reactions of α-imino ketones, derived from arylglyoxals, with (trifluoromethyl)trimethylsilane (CF3SiMe3) in DME solution, in the presence of catalytic amount of CsF, at room temperature, yield O-silylated β-imino alcohols in the chemoselective manner. Subsequent reduction of these products with NaBH4 in ethanolic solution leads to the corresponding β-(N-alkyl)amino-α-trifluoromethyl alcohols in

  在室温下，在催化量的CsF存在下，芳基乙二醛衍生的α-亚氨基酮与（三氟甲基）三甲基硅烷（CF 3 SiMe 3）在DME溶液中反应，生成O-甲硅烷基化的β-亚氨基醇。化学选择性方式。随后在乙醇溶液中用NaBH 4还原这些产物可得到相应的β-（N-烷基）氨基-α-三氟甲基醇，收率良好至极佳。对映体纯的α-亚氨基酮（Ar = Ph或p -MeOC 6 H 4）的三氟甲基化，带有手性助剂，PhCH（Me）基团连接到氮原子上，产生非对映体产物的混合物，其比例为约3。3：2。
• 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.
• Enantioselective additions of (trifluoromethyl)trimethylsilane to α-imino ketones derived from aryl glyoxals
  作者：Emilia Obijalska、Grzegorz Mlostoń、Alice Six

  DOI：10.1016/j.tetlet.2013.02.093

  日期：2013.5

  Chemoselective additions of (trifluoromethyl)trimethylsilane to α-imino ketones derived from aryl glyoxals in the presence of a catalytic amount of enantiomerically pure ammonium bromides, derived from Cinchona alkaloids and K2CO3 led to O-silylated β-imino alcohols. Subsequent reduction of these products with NaBH4 gave β-(N-alkyl)amino-α-trifluoromethyl alcohols for which the ee values were 30–71%

  在催化量的对映体纯的溴化铵，金鸡纳生物碱和K 2 CO 3的存在下，将（三氟甲基）三甲基硅烷化学选择性加成到芳基乙二醛的α-亚氨基酮上，生成O-甲硅烷基化的β-亚氨基醇。随后用NaBH 4还原这些产物，得到β-（N-烷基）氨基-α-三氟甲基醇，在最佳条件下，其ee值为30 – 71％。根据在手性溶剂化剂存在下记录的1 H或19 F NMR光谱确定最终产物的对映体过量。