4-二苄氨基丁烷-2-酮 | 26734-07-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 中文名称: 4-二苄氨基丁烷-2-酮
• 英文名称: 4-dibenzylamino-2-butanone
• 英文别名: N,N-dibenzyl-2-aminoethyl-methylketone；4-[bis(phenylmethyl)amino]butan-2-one；4-(N-dibenzylamino)butan-2-one；4-(dibenzylamino)-2-butanone；N,N,-Dibenzyl-2-aminoethyl methyl ketone；N,N-dibenzyl-2-aminoethyl methyl ketone；4-(Dibenzylamino)butan-2-one
• CAS: 26734-07-6
• 化学式: C₁₈H₂₁NO
• mdl: MFCD01002923
• 分子量: 267.371
• InChiKey: UUVNGPGLPIICOR-UHFFFAOYSA-N

物化性质

• 熔点：
  56.5-58.0 °C(Solv: ligroine (8032-32-4))
• 沸点：
  378.2±30.0 °C(Predicted)
• 密度：
  1.055±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  20
• 可旋转键数：
  7
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.277
• 拓扑面积：
  20.3
• 氢给体数：
  0
• 氢受体数：
  2

安全信息

• 海关编码：
  2922399090
• 储存条件：
  室温

反应信息

• 作为反应物：
  描述：

  4-二苄氨基丁烷-2-酮 在 palladium on activated charcoal sodium tetrahydroborate 、 氢气 作用下， 以 甲醇 、 乙醇 为溶剂， 10.0~20.0 ℃ 、101.33 kPa 条件下， 反应 9.0h， 生成 1-benzylamino-3-hydroxybutane
  参考文献：
  名称：

  Structure−Immunosuppressive Activity Relationships of New Analogues of 15-Deoxyspergualin. 2. Structural Modifications of the Spermidine Moiety

  摘要：

  A series of new analogues of 15-deoxyspergualin (DSG), an immunosuppressive agent commercialized in Japan, was synthesized and tested in a graft-versus-host disease (GVHD) model in mice. Various substitutions of the spermidine "D" region were made in order to determine its optimum structure in terms of in vivo immunosuppressive activity. Various positions of methylation were first investigated leading to the discovery of the monomethylated malonic derivative 56h in which the pro-R hydrogen of the methylene a to the primary amine of the spermidine moiety has been replaced by a methyl group. Synthesis of the similarly methylated analogue of the previously reported glycolic derivative LF 08-0299 afforded 60e which demonstrated a powerful activity at a dose as low as 0.3 mg/kg in the GVHD model and was much more potent than DSG in the demanding heart allotransplantation model in rats. The improvement of in vivo activity was supposed to be related to an increase of the metabolic stability of the methylated analogues compared to the parent molecules. Due to its very low active dose, compatible with a subcutaneous administration in humans, and its favorable pharmacological and toxicological profile, 60e was selected as a candidate for clinical evaluation.

  DOI：

  10.1021/jm991043x
• 作为产物：
  描述：

  2-methyl-N,N-bis(phenylmethyl)-1,3-dithiane-2-ethanamine 在 溶剂黄146 、 2-碘酰基苯甲酸 作用下， 以 水 、 二甲基亚砜 为溶剂， 反应 6.0h， 以96%的产率得到4-二苄氨基丁烷-2-酮
  参考文献：
  名称：

  邻碘苯甲酸 (IBX) 作为操作含氮和含硫底物的可行试剂：IBX 介导的胺氧化和二噻烷脱保护的范围、一般性和机制

  摘要：

  发现邻碘苯甲酸 (IBX) 是一种用途广泛的高价碘 (V) 试剂，除了促进二硫缩醛和二硫缩酮的氧化裂解外，还可以有效介导胺的脱氢。通过开发相关的基于 IBX 的协议，发现大量有用的合成中间体，包括亚胺、肟、酮和芳香族 N-杂环，在特别温和的条件下很容易获得。对这些转化的进一步研究导致了对有价值的机械细节的阐明，从而得出结论，它们是通过离子而不是单电子转移 (SET) 途径进行的。

  DOI：

  10.1021/ja0400382

文献信息

• Micellar Solution of Sodium Dodecyl Sulfate (SDS) Catalyzes Facile Michael Addition of Amines and Thiols to ?,?-Unsaturated Ketones in Water under Neutral Conditions
  作者：H. Firouzabadi、N. Iranpoor、A.?A. Jafari

  DOI：10.1002/adsc.200404348

  日期：2005.4

  Sodium dodecyl sulfate (SDS) catalyzes facile Michael additions of amines and thiols to α,β-unsaturated ketones under neutral micellar conditions to afford the corresponding Michael adducts in good to high yields.

  十二烷基硫酸钠（SDS）在中性胶束条件下催化胺和硫醇向α ，β-不饱和酮的容易的迈克尔加成反应，从而以高产率高收率地提供相应的迈克尔加合物。
• A New Two-Step Preparation of Pyrroles from β-Amino Ketones Utilizing Trimethylsilyldiazomethane
  作者：Tsutomu Yagi、Toyohiko Aoyama、Takayuki Shioiri

  DOI：10.1055/s-1997-1552

  日期：1997.9

  Lithium trimethylsilyldiazomethane smoothly reacted with N-substituted β-amino ketones to give 2-pyrrolines which were easily converted to the corresponding pyrroles by treatment with MnO2 (CMD, chemical manganese dioxide). The reaction with N,N-disubstituted β-amino ketones followed by oxidation with CMD also afforded pyrroles.

  三甲基硅烷基二氮甲基锂与N-取代的β-氨基酮顺利反应，生成2-吡咯啉，这些2-吡咯啉通过用MnO2（CMD，化学二氧化锰）处理，可以轻易转化为相应的吡咯。与N,N-二取代的β-氨基酮反应后，用CMD氧化也得到了吡咯。
• Bismuth Nitrate-Catalyzed Versatile Michael Reactions
  作者：Neeta Srivastava、Bimal K. Banik

  DOI：10.1021/jo026550s

  日期：2003.3.1

  Bismuth nitrate-catalyzed versatile Michael reaction was developed to reduce the complications that characterize the current standard Michael reaction and used for facile preparation of organic compounds of widely different structures. For example, several substituted amines, imidazoles, thio compounds, indoles, and carbamates were prepared at room temperature by following this method. In contrast

  硝酸铋催化的通用迈克尔反应的开发是为了减少目前标准迈克尔反应所特有的复杂性，并用于方便地制备结构迥异的有机化合物。例如，按照该方法在室温下制备几种取代的胺，咪唑，硫代化合物，吲哚和氨基甲酸酯。与使用许多酸性催化剂的现有方法相比，该方法非常通用，简单，高产率，环境友好并且耐氧气和湿气。但是，目前尚不了解硝酸铋在该反应中的促进作用。
• Aza-Michael Reactions in Ionic Liquids. A Facile Synthesis of β-Amino Compounds
  作者：J. S. Yadav、B. V. S. Reddy、A. K. Basak、A. V. Narsaiah

  DOI：10.1246/cl.2003.988

  日期：2003.11

  Electron-deficient olefins undergo smoothly aza-Michael reactions with a wide range of amines in ionic liquids in the absence of any acid catalyst to produce the corresponding β-amino compounds in excellent yields with high 1,4-selectivity. The recovered ionic liquids can be reused in subsequent reactions without loss of activity. Owing to the high polarity of ionic liquids, the enones show enhanced reactivity thereby reducing reaction times and improving the yields significantly.

  缺电子烯烃在无任何酸催化剂的情况下，能顺利地在离子液体中与多种胺类进行aza-Michael反应，高效地生成高1,4-选择性的相应β-氨基化合物。回收的离子液体可在后续反应中重复使用，且活性无损失。由于离子液体的高极性，使得烯酮表现出增强的反应活性，从而缩短反应时间，显著提高产率。
• Cellulose-Supported Copper(0) Catalyst for Aza-Michael Addition
  作者：K. Reddy、Nadakudity Kumar

  DOI：10.1055/s-2006-949623

  日期：2006.9

  Cellulose-supported copper(0) efficiently catalyzes the aza-Michael reaction of N-nucleophiles, such as amines and imidazoles with α,β-unsaturated compounds to produce the corresponding β-amino compounds and N-substituted imidazoles in excellent yields. The reactions are facile and the recovered catalyst is used for several cycles with consistent activity.

  纤维素负载的零价铜可高效催化亲核试剂（如胺和咪唑）与α,β-不饱和化合物进行的aza-迈克尔反应，从而以优异的产率生成相应的β-氨基酸化合物和N-取代咪唑。这些反应操作简便，且回收的催化剂可在连续多个循环中保持一致的活性。