3-(diphenylamino)-1-propanol | 52850-23-4

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: 3-(diphenylamino)-1-propanol
• 英文别名: N,N-phenyl-(3-hydroxypropyl)-amine；3-(Diphenylamino)propan-1-ol；3-(N-phenylanilino)propan-1-ol
• CAS: 52850-23-4
• 化学式: C₁₅H₁₇NO
• 分子量: 227.306
• InChiKey: HUWAJIQFAFTNIW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  17
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.2
• 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-(diphenylamino)-1-propanol 在 四溴化碳 、 三苯基膦 作用下， 以 乙腈 为溶剂， 反应 1.0h， 以97%的产率得到1-bromo-3-propyldiphenylamine
  参考文献：
  名称：

  一系列新型9- [3-（顺3,5-二甲基-1-哌嗪基）丙基]咔唑（rimcazole）类似物在单胺转运蛋白和sigma受体的结构活性关系。

  摘要：

  9- [3-（顺式-3,5-二甲基-1-哌嗪基）丙基]咔唑（rimcazole）的特征是作为sigma受体拮抗剂，以适度的亲和力与多巴胺转运蛋白结合（K（i）= 224 nM） 。尽管rimcazole和可卡因在多巴胺转运蛋白上的结合亲和力相当，但rimcazole仅降低了小鼠的自发活动并拮抗可卡因产生的刺激作用。尽管已提出可卡因作用减弱的神经化学机制尚不清楚，但已建议在多巴胺转运蛋白的低亲和力位点/状态相互作用。为了进一步探索这类化合物，设计并合成了一系列rimcazole类似物。[（3）H] WIN 35的位移，428在大鼠尾状-丘脑中的多巴胺转运蛋白上的结合表明，rimcazole上的芳香取代没有很好的耐受性，通常对3,6-dibromo的亲和力显着降低（5; K（i）= 3890 nM），1， 3，6-三溴（6; K（i）= 30300 nM），3-氨基（8; K（i）= 2400

  DOI：

  10.1021/jm9902943
• 作为产物：
  描述：

  N-烯丙基-N-苯基苯胺 在 9-borabicyclo[3.3.1]nonane dimer 、 sodium hydroxide 、 双氧水 作用下， 以 四氢呋喃 为溶剂， 反应 18.0h， 以71%的产率得到3-(diphenylamino)-1-propanol
  参考文献：
  名称：

  A Chimeric Ligand Approach Leading to Potent Antiprion Active Acridine Derivatives:  Design, Synthesis, and Biological Investigations

  摘要：

  Human transmissible neurodegenerations including Creutzfeldt-Jakob disease are unique, since they are caused by prions, an infectious agent that replicates without nucleic acids but instead by inducing conversion of a host-resident normal prion protein to a misfolded conformational isoform. For pharmacotherapy of these unusual diseases, tricyclic heterocyclic compounds such as quinacrine have been considered, but with ambiguous success in vivo, so far. On the basis of the synergistic antiprion effects of quinacrine and iminodibenzyl derivatives, we introduce a novel class of potential pharmaceuticals representing structural chimeras of quinacrine and imipramine analogues. We describe the chemical synthesis and bioassays of a focused library of these compounds. The most potent target compound 2a revealed an EC50 value of 20 nM determined with a cell model of prion disease, thus substantially improving the antiprion efficacy of quinacrine.

  DOI：

  10.1021/jm060773j

文献信息

• Gas-phase pyrolytic reaction of 3-anilino-1-propanol derivatives: kinetic and mechanistic study
  作者：M.R. Ibrahim、N.A. Al-Awadi、Y.A. Ibrahim、M. Patel、S. Al-Awadi

  DOI：10.1016/j.tet.2007.03.090

  日期：2007.5

  3-Anilino-1-propanol derivatives 4a–c, 5a–c, 6a–c containing primary, secondary, and tertiary alcohols and PhNH, PhNMe, and (Ph)2N were prepared and subjected to gas-phase pyrolysis in a static reaction system. The pyrolytic reactions were homogeneous and followed a first-order rate equation. Reactions took place by retro-ene process, with the exception of compounds 5a and 5b. Analysis of the pyrolysate

  制备包含伯，仲和叔醇以及PhNH，PhNMe和（Ph）2 N的3-苯胺-1-丙醇衍生物4a – c，5a – c，6a – c，并在静态下进行气相热解反应系统。热解反应是均相的，并且遵循一阶速率方程。除化合物5a和5b外，反应通过逆烯法进行。对热解产物的分析表明产物为N取代的苯胺和羰基化合物。根据消除途径的合理过渡态，对九种被研究的3-氨基醇中每一种的动力学结果和产物分析进行了合理化处理。
• Defluorinative Alkylation of 1-Trifluoromethyl Alkenes with Alkyl Radicals Derived from Visible-Light Induced Deoxygenation of Xanthate Salts: Synthesis of gem-Difluoroalkenes
  作者：Xin Li、Yan Jiao、Lifei Han、Jinwei Sun、Xuan Zhang

  DOI：10.1039/d3ob00333g

  日期：——

  difluoroallylation of alkyl precursors with trifluoromethyl alkenes for the synthesis of gem-difluoroalkenes is appealing and challenging. We herein describe a visible light-induced approach that enables deoxygenative difluoroallylation of abundant alcohols via xanthate salts with trifluoromethyl alkenes, where xanthate salts work as a photoreductant and an alkylating reagent, avoiding the use of external

  用于合成偕二氟烯烃的烷基前体与三氟甲基烯烃的无催化剂和无金属二氟烯丙基化具有吸引力和挑战性。我们在此描述了一种可见光诱导的方法，该方法能够通过黄原酸盐与三氟甲基烯烃对丰富的醇进行脱氧二氟烯丙基化，其中黄原酸盐作为光还原剂和烷基化试剂，避免使用外部催化剂。这种一锅法可以容纳具有良好功能耐受性的伯醇、仲醇和叔醇，并成功应用于天然产物和药物的后期功能化。
• Omega-quaternary ammonium alkyl esters and thioesters of acidic nonsteroidal antiinflammatory drugs
  申请人：SYNTEX PHARMACEUTICALS INTERNATIONAL LIMITED

  公开号：EP0289262A2

  公开（公告）日：1988-11-02

  Quaternary ammonium alkyl esters and thioesters of acidic nonsteroidal anti-inflammatory drugs (NSAIDs) are disclosed. These esters and thioesters display the anti-­inflammatory profile of the parent NSAIDs with greatly reduced gastrointestinal irritancy, providing a more favorable separation of therapeutic activity and toxicological side effects than the parent NSAIDs.

  本发明公开了酸性非甾体抗炎药（NSAIDs）的季铵烷基酯和硫代酯。这些酯类和硫代酯类具有母体非甾体抗炎药的抗炎特性，但胃肠道刺激性大大降低，与母体非甾体抗炎药相比，能更有效地将治疗活性和毒副作用分开。
• PHENYLCARBOXYLIC ACID DERIVATIVES
  申请人：OTSUKA PHARMACEUTICAL CO., LTD.

  公开号：EP0394440A1

  公开（公告）日：1990-10-31

  Phenylcarboxylic acid derivatives represented by formula (I), and their salts, wherein R1 and R2 each represents H, halogen, alkyl, haloalkyl, alkanoyl, cycloalkyl, nitro, amino, -0-D-R5 (wherein D represents alkylene, and R5 represents H, amino, morpholino, carboxyl, phthalimido, phenyl or epoxy), substituted or unsubstituted phenoxy, substituted or unsubstituted phenylalkylamino, carboxylalkenyl or, when taken together, represent alkylenedioxy: R3 represents H, -E-R6 (wherein E represents alkylene, and R6 represents H carboxyl, cyano, OH, phenylalkoxy or halogen-substituted phenyl or phenylcarbamoyl) -CO-G-R7 (wherein G represents alkylene, and R7represents H or substituted or unsubstituted phenylcarbamoyl), substituted or unsubstituted benzoyl, alkenyl, carbamoyl, phenyl or halophenyl: R4 represents H, alkyl: A represents alkylene, cycloalkyl ring-fuzed alkylene or alkenylene; B represents alkylene or alkenylene; and ℓ represents 0 or 1. These compounds have an activity of inhibiting synthesis of fatty acids and cholesterol, and are useful for treating hyperlipemia, arteriosclerosis, obesity and diabetes.

  由式(I)代表的苯基羧酸衍生物及其盐，其中 R1 和 R2 各自代表 H、卤素、烷基、卤代烷基、烷酰基、环烷基、硝基、氨基、-0-D-R5（其中 D 代表亚烷基，R5 代表 H、氨基、吗啉基、羧基、邻苯二甲酰亚胺基、苯基或环氧基）、取代或未取代的苯氧基、取代或未取代的苯烷基氨基、羧基烯基，或者合在一起代表亚烷基二氧基：R3代表H、-E-R6（其中E代表亚烷基，R6代表H羧基、氰基、OH、苯基烷氧基或卤素取代的苯基或苯基氨基甲酰基）、取代或未取代的苯甲酰基、烯基、氨基甲酰基、苯基或卤代苯基：R4 代表 H、烷基：A 代表亚烷基、环烷基环化亚烷基或烯基；B 代表亚烷基或烯基；ℓ 代表 0 或 1。这些化合物具有抑制脂肪酸和胆固醇合成的活性，可用于治疗高脂血症、动脉硬化、肥胖症和糖尿病。
• AQUEOUS SILYLATED URETHANE COMPOSITION, AQUEOUS ADHESIVES FOR WRAPPING, AND AQUEOUS CONTACT ADHESIVES
  申请人：KONISHI CO., LTD.

  公开号：EP1607423A1

  公开（公告）日：2005-12-21

  A water-based silylated urethane composition is used as a water-based adhesive that has high safety, develops satisfactory tackiness in a short time and has excellent initial bond strength. The water-based silylated urethane composition contains following Components (A), (B) and (C): (A) a urethane prepolymer containing an anionic group and a tertiary amino group and having a terminal alkoxysilyl group, the urethane prepolymer (A) being a reaction product of an anionic-group-free polyol compound (A1), an anionic-group-containing polyol compound (A2), a compound (A3) containing a tertiary amino group and an isocyanate-reactive group, a polyisocyanate compound (A4), an alkoxysilane compound (A5) containing an isocyanate-reactive group, and an amine-based chain extender (A6); (B) a basic compound; and (C) water

  一种水基硅烷化聚氨酯组合物可用作水基粘合剂，它具有很高的安全性，能在短时间内产生令人满意的粘性，并具有出色的初始粘合强度。水基硅烷化聚氨酯组合物包含以下成分（A）、（B）和（C）： (A) 含有阴离子基团和叔氨基且具有末端烷氧基硅烷基团的聚氨酯预聚物，聚氨酯预聚物 (A) 是不含阴离子基团的多元醇化合物 (A1)、含阴离子基团的多元醇化合物 (A2) 的反应产物、一种含有叔氨基和异氰酸酯反应基团的化合物 (A3)、一种多异氰酸酯化合物 (A4)、一种含有异氰酸酯反应基团的烷氧基硅烷化合物 (A5) 和一种胺基扩链剂 (A6)； (B) 碱性化合物；以及 (C) 水