3-(N,N-Dibenzylamino)-1-phenyl-propan-1-on | 122377-71-3

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 3-(N,N-Dibenzylamino)-1-phenyl-propan-1-on
• 英文别名: 3-(dibenzylamino)-1-phenylpropan-1-one；1-Propanone, 3-[bis(phenylmethyl)amino]-1-phenyl-
• CAS: 122377-71-3
• 化学式: C₂₃H₂₃NO
• 分子量: 329.442
• InChiKey: XJRDLJPYAQCFKU-UHFFFAOYSA-N

物化性质

• 熔点：
  37-40 °C
• 沸点：
  464.8±33.0 °C(Predicted)
• 密度：
  1.101±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.6
• 重原子数：
  25
• 可旋转键数：
  8
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  20.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  3-(N,N-Dibenzylamino)-1-phenyl-propan-1-on 在 sodium tetrahydroborate 作用下， 以 甲醇 为溶剂， 以85%的产率得到3-(dibenzylamino)-1-phenylpropan-1-ol
  参考文献：
  名称：

  A Straightforward and Efficient Method for the Synthesis of Diversely Substituted β-Aminoketones and γ-Aminoalcohols from 3-(N,N-Dimethylamino)propiophenones as Starting Materials

  摘要：

  Libraries of novel beta-aminoketones and gamma-aminoalcohols showing a wide structural diversity were easily obtained from a simple approach, using 3-(N,N-dimethylamino)propiophenone derivatives as key starting material. The procedure involved initially an N-alkylation of secondary benzylamines with propiophenone salts yielding the desired beta-aminoketones. Chemical or catalytic reduction of their carbonyl groups provided the final gamma-aminoalcohols in good yields. This protocol proved to be convenient as an alternative route for the synthesis of the local anesthetic Falicain (R) and for the topic antifungal drug Naftifine (R).

  DOI：

  10.5935/0103-5053.20130177
• 作为产物：
  描述：

  苯甲醛 在 manganese(IV) oxide 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 7.5h， 生成 3-(N,N-Dibenzylamino)-1-phenyl-propan-1-on
  参考文献：
  名称：

  炔酮还原加氢胺化无金属合成β-氨基酮

  摘要：

  本研究描述了一种在非常温和的无金属条件下通过炔烃的还原加氢胺化合成 β-氨基酮的级联方法。它允许炔酮和胺快速转化为相应的β-氨基酮，具有广泛的底物范围和多种功能。这种简单易行的反应过程可成功应用于普罗克生和普罗哌卡因的合成，为合成具有β-氨基酮骨架的药物分子提供了潜在的选择。

  DOI：

  10.1039/d2cc00169a

文献信息

• Cu-Catalyzed Sequential Dehydrogenation–Conjugate Addition for β-Functionalization of Saturated Ketones: Scope and Mechanism
  作者：Xiaoming Jie、Yaping Shang、Xiaofeng Zhang、Weiping Su

  DOI：10.1021/jacs.6b01337

  日期：2016.5.4

  The first copper-catalyzed direct β-functionalization of saturated ketones is reported. This protocol enables diverse ketones to couple with a wide range of nitrogen, oxygen and carbon nucleophiles in generally good yields under operationally simple conditions. The detailed mechanistic studies including kinetic studies, KIE measurements, identification of reaction intermediates, EPR and UV-visible

  报道了第一个铜催化的饱和酮直接β-官能化。该协议使不同的酮能够在操作简单的条件下以通常良好的产率与广泛的氮、氧和碳亲核试剂结合。进行了详细的机理研究，包括动力学研究、KIE 测量、反应中间体的鉴定、EPR 和紫外可见实验，结果表明该反应是通过一种新型的基于自由基的脱氢生成烯酮和随后的共轭加成序列进行的。
• Cer(IV)oxidationen von β-Aminoketonen, 6. Mitt.: Untersuchungen zum Reaktionsverlauf
  作者：Ulrike Holzgrabe

  DOI：10.1002/ardp.19893220304

  日期：——

  Die Cer(IV)sulfat‐Oxidationen von N‐Benzyl‐4‐piperidonen sind durch einen radikalischen Reaktionsverlauf gekennzeichnet: die Cyclisierungsprodukte, die Methanobenzazocine 2, werden über ein Radikal an C‐3 gebildet, für die Dehydrierungsreaktion zu 3 und 4 sind intermediär gebildete Peroxyradikale verantwortlich.

  N - 苄基 - 4 - 哌啶酮的硫酸铈 (IV) 氧化的特征在于自由基反应过程：环化产物，甲苯并唑嗪 2，通过 C-3 处的自由基形成，用于脱氢反应为 3 和 4中间体过氧自由基负责。
• Simple Synthetic Equivalents for the β-(N,N-Disubstituted)ethylamino Acyl Cation Synthon and their Applications
  作者：V. Selvamurugan、Indrapal Singh Aidhen

  DOI：10.1055/s-2001-18439

  日期：——

  Various N,N-disubstituted-β-amino-N-methoxy-N-methylpropanamides 3a-i were prepared which served as an excellent β-aminoacyl cation equivalents. These were used to prepare β-amino ketones 1, pharmacologically active tertiary 1-(3,3-diarylpropyl)amines 7a-c, and the interesting C-glycoside 8.

  合成了多种N,N-二取代的β-氨基-N-甲氧基-N-甲基丙酰胺3a-i，它们作为优秀的β-氨基酰基阳离子等价物。这些化合物被用于制备β-氨基酮1，具有药理活性的三级1-(3,3-二芳基丙基)胺7a-c，以及有趣的C-糖苷8。
• Covert Mannich Reaction via Carbon Transfer
  作者：Huan Gu、Yuan Guo、Zhen Shi

  DOI：10.1080/00397910600941299

  日期：2006.11.1

  1,3-Dimethylbenzimidazolidine reacts with ketones, which can provide activating a hydrogens and primary or secondary amines under acidic conditions, to yield aminomethylation derivatives by a covert Mannich reaction.
• Structure−Immunosuppressive Activity Relationships of New Analogues of 15-Deoxyspergualin. 2. Structural Modifications of the Spermidine Moiety
  作者：Luc Lebreton、Eric Jost、Bertrand Carboni、Jocelyne Annat、Michel Vaultier、Patrick Dutartre、Patrice Renaut

  DOI：10.1021/jm991043x

  日期：1999.11.1

  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.