3-(dibenzylamino)-1-phenylpropan-1-ol | 252353-90-5

• 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: 3-(dibenzylamino)-1-phenylpropan-1-ol
• CAS: 252353-90-5
• 化学式: C₂₃H₂₅NO
• 分子量: 331.458
• InChiKey: DRTBFTBHRKYUFF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.5
• 重原子数：
  25
• 可旋转键数：
  8
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  23.5
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  3-(dibenzylamino)-1-phenylpropan-1-ol 在 palladium on activated charcoal sodium azide 、 氢气 、 sodium carbonate 、 三乙胺 、 potassium iodide 作用下， 以 甲醇 、 二氯甲烷 、 二甲基亚砜 、 正丁醇 为溶剂， 20.0~45.0 ℃ 、101.33 kPa 条件下， 反应 24.0h， 生成 4-[(3-Azido-3-phenylpropyl)-benzylamino]butanenitrile
  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malonic derivative 56h in which the pro-R hydrogen of the methylene a to the primary amine of the spermidine moiety has been replaced by a methyl group.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：

  苯乙酮 在 sodium tetrahydroborate 作用下， 以 甲醇 、 异丙醇 为溶剂， 生成 3-(dibenzylamino)-1-phenylpropan-1-ol
  参考文献：
  名称：

  Synthesis and appetite suppressant activity of 1-aryloxy-2-substituted aminomethyltetrahydronaphthalenes as conformationally rigid analogues of fluoxetine

  摘要：

  Several 1-aryloxy-2-substituted aminomethyltetrahydronaphthalenes (7-21) as conformationally rigid analogues of fluoxetine were synthesized and evaluated for their anorexigenic and antidepressant activities. For SAR studies the related acyclic analogues (22-27) were also prepared. Out Of the 21 synthesized compounds, 10 compounds (9, 10, 11, 15, 16 18, 21, 22: 23 and 27) exhibited significant anorexigenic activity (at 75 mu mol/kg). Interestingly, all the compounds (7-20, 22-26) were devoid of antidepressant effect, except for compounds 21 and 27 in which the antidepressant activity was retained. Compound 16 emerged as the most active compound of the series with better anorexigenic activity (97.92%) compared to fluoxetine (76.251/6) and even with a clinically used drug sibutramine, thus providing a new Structural lead for appetite suppressants. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2005.11.032

文献信息

• Transformation of α-Substituted Propanols into γ-Amino Alcohols through Nickel-Catalyzed Amination on the Terminal γ-Carbon of Propanols
  作者：Satoshi Ueno、Ryoichi Kuwano、Kazumi Usui

  DOI：10.1055/s-0030-1260536

  日期：2011.6

  A nickel-phosphine complex was found to be effective as the catalyst for the transformation of alcohols into β-enaminones, which was successively converted into γ-amino alcohols by a conventional reductant. The sequential transformation is equivalent to the carbon-nitrogen bond formation at the γ-position of saturated alcohols.

  研究发现，镍膦络合物可作为催化剂，有效地将醇转化为δ-烯丙酮，再通过传统还原剂将δ-烯丙酮连续转化为δ-氨基醇。这种连续转化相当于在饱和醇的δ³位形成碳氮键。
• A Straightforward and Efficient Method for the Synthesis of Diversely Substituted β-Aminoketones and γ-Aminoalcohols from 3-(<i>N,N</i>-Dimethylamino)propiophenones as Starting Materials
  作者：Rodrigo Abonia、Danny Arteaga、Juan Castillo、Braulio Insuasty、Jairo Quiroga、Alejandro Ortíz

  DOI：10.5935/0103-5053.20130177

  日期：——

  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).
• US4313896A
  申请人：——

  公开号：US4313896A

  公开（公告）日：1982-02-02
• 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.
• Synthesis and appetite suppressant activity of 1-aryloxy-2-substituted aminomethyltetrahydronaphthalenes as conformationally rigid analogues of fluoxetine
  作者：Kalpana Bhandari、Shipra Srivastava、Girija Shankar、Chandishwar Nath

  DOI：10.1016/j.bmc.2005.11.032

  日期：2006.4

  Several 1-aryloxy-2-substituted aminomethyltetrahydronaphthalenes (7-21) as conformationally rigid analogues of fluoxetine were synthesized and evaluated for their anorexigenic and antidepressant activities. For SAR studies the related acyclic analogues (22-27) were also prepared. Out Of the 21 synthesized compounds, 10 compounds (9, 10, 11, 15, 16 18, 21, 22: 23 and 27) exhibited significant anorexigenic activity (at 75 mu mol/kg). Interestingly, all the compounds (7-20, 22-26) were devoid of antidepressant effect, except for compounds 21 and 27 in which the antidepressant activity was retained. Compound 16 emerged as the most active compound of the series with better anorexigenic activity (97.92%) compared to fluoxetine (76.251/6) and even with a clinically used drug sibutramine, thus providing a new Structural lead for appetite suppressants. (c) 2005 Elsevier Ltd. All rights reserved.