3-(dimethylamino)-1-(2-hydroxyphenyl)propan-1-one hydrochloride | 1639-35-6

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 3-(dimethylamino)-1-(2-hydroxyphenyl)propan-1-one hydrochloride
• 英文别名: β-dimethylamino-2-hydroxy-propiophenone hydrochloride；Propiophenone, 3-dimethylamino-2'-hydroxy-, hydrochloride；3-(dimethylamino)-1-(2-hydroxyphenyl)propan-1-one;hydrochloride
• CAS: 1639-35-6
• 化学式: C₁₁H₁₅NO₂*ClH
• 分子量: 229.707
• InChiKey: CYMMEXYPWIUVOF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.95
• 重原子数：
  15
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  40.5
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  3-(dimethylamino)-1-(2-hydroxyphenyl)propan-1-one hydrochloride 在 sodium hydride 作用下， 以 二氯甲烷 为溶剂， 反应 0.83h， 生成 (E)-3-imidazol-1-yl-N,N-dimethyl-3-(2-propoxyphenyl)prop-2-en-1-amine
  参考文献：
  名称：

  Synthesis and antifungal activity of new 1-vinylimidazoles

  摘要：

  Carbonyl compounds I were subjected to an imidazole transfer reaction with N,N'-sulfinyldiimidazole or N,N'-carbonyldiimidazole to obtain the diimidazole II and the monoimidazole III. Various 1-vinylimidazoles IV, derived from o-hydroxyacetophenones by imidazole transfer reaction, were alkylated to furnish the title compounds V. The structure-activity relationships of these 1-vinylimidazole compounds V are described.

  DOI：

  10.1021/jm00391a014
• 作为产物：
  描述：

  盐酸二甲胺 、 2'-羟基苯乙酮 在 盐酸 作用下， 以 乙醇 为溶剂， 以29%的产率得到3-(dimethylamino)-1-(2-hydroxyphenyl)propan-1-one hydrochloride
  参考文献：
  名称：

  N-Vinylimidazoles and -triazoles and pharmaceutical compositions containing them

  摘要：

  公开号：

  EP0227100B1

文献信息

• Role of the X Coligands in Cyclometalated [Ni(Phbpy)X] Complexes (HPhbpy = 6-Phenyl-2,2′-bipyridine)
  作者：Nicolas Vogt、Aaron Sandleben、Lukas Kletsch、Sascha Schäfer、Mason T. Chin、David A. Vicic、Gerald Hörner、Axel Klein

  DOI：10.1021/acs.organomet.1c00237

  日期：2021.6.14

  The coligand X was varied in the organonickel complexes [Ni(Phbpy)X] (X = F, Cl, Br, I, C6F5) carrying the anionic tridentate C∧N∧N ligand 6-(phen-2-ide)-2,2′-bipyridine (Phbpy–) to study its effect on electronic structures of these complexes and their activity in Negishi-like C–C cross-coupling catalysis. The complexes were synthesized from the precursor [Ni(COD)2] (COD = 1,5-cyclooctadiene) by chelate-assisted

  携带阴离子三齿 C ∧ N ∧ N 配体 6-(phen-2-ide ) 的有机镍配合物 [Ni(Phbpy)X] (X = F, Cl, Br, I, C 6 F 5 ) 中的共配体X )-2,2'-联吡啶 (Phbpy – ) 研究其对这些配合物的电子结构的影响及其在 Negishi 样 C-C 交叉偶联催化中的活性。该配合物由前体 [Ni(COD) 2]（COD = 1,5-环辛二烯）通过螯合物辅助氧化加成到原配体 6-（2-卤代苯基）-2,2'-联吡啶的苯基 C-X 键中）并以红色粉末形式获得。携带卤化物替代物 X = OMe、OTf（三氟甲磺酸盐）的原配体 X–Phbpy 在该反应中失败。单晶 XRD 使我们能够将 [Ni(Phbpy)Cl] 和 [Ni(Phbpy)I] 的结构添加到先前报道的 Br 衍生物中。循环伏安法显示出对X = C可逆减少6 ˚F 5，氟，氯，而Br和I
• N-Alkylation of benzimidazoles with ketonic Mannich bases and the reduction of the resulting 1-(3-oxopropyl)benzimidazoles
  作者：Gheorghe Roman

  DOI：10.2478/s11532-012-0062-x

  日期：2012.10.1

  position 2, and 5,6-dimethylbenzimidazole have been alkylated at N 1 with ketonic Mannich bases derived from acetophenones, acetylnaphthalenes, 2-acetylthiophene and 1-tetralone to afford a series of novel 1-(3-oxopropyl)benzimidazoles. The reduction of these transamination products with NaBH4 in methanol produced the corresponding 1-(3-hydroxypropyl)benzimidazoles in excellent yields.

  苯并咪唑，在2位被不同取代的苯并咪唑和5,6-二甲基苯并咪唑已在 N 1被衍生自苯乙酮，乙酰萘，2-乙酰基噻吩和1-四氢萘酮的酮基曼尼希碱烷基化， 从而制得一系列新型的1-（3-氧代丙基） ）苯并咪唑 在甲醇中用NaBH 4还原这些氨基转移产物可产生相应的1-（3-羟丙基）苯并咪唑类，产率很高。
• A Novel Antifungal Agent with Broad Spectrum: 1-(4-Biphenylyl)-3-(1<i>H</i>-imidazol-1-yl)-1-propanone
  作者：Gheorghe Roman、Mihai Mareş、Valentin Năstasă

  DOI：10.1002/ardp.201200287

  日期：2013.2

  carbonyl function of the imidazole–ketones in the previous series by means of NaBH4. All of the compounds were evaluated for antifungal activity against 16 strains of Candida, and 3‐(1H‐imidazol‐1‐yl)‐1‐(4‐biphenylyl)‐1‐propanone emerged as a broad‐spectrum antifungal agent. Several 3‐(1H‐imidazol‐1‐yl)‐1‐(2′‐(substituted benzyl)oxyphenyl)‐1‐propanones were also active towards Candida kefyr.

  通过咪唑与3-二甲氨基-1-（取代芳基）-1-丙酮盐酸盐的N-烷基化合成一系列（1-取代芳基）-3-（1H-咪唑-1-基）-1-丙酮（酮曼尼希碱）。第二系列 N1 取代的咪唑是通过使用 NaBH4 还原前一系列中咪唑-酮的羰基官能团而获得的。评估了所有化合物对 16 种念珠菌的抗真菌活性，3-(1H-咪唑-1-基)-1-(4-联苯基)-1-丙酮作为广谱抗真菌剂出现。几种 3-(1H-咪唑-1-基)-1-(2'-(取代苄基)氧基苯基)-1-丙酮对克菲尔念珠菌也有活性。
• A Modified Synthesis of 4-Chromanones
  作者：Brian Cox、Roger D. Waigh

  DOI：10.1055/s-1989-27369

  日期：——

  Problems in the synthesis of 4-chromanones by condensation of 2-hydroxyacetophenones with formaldehyde can be avoided by the isolation of the Mannich base hydrochlorides and cyclization by titration with potassium hydroxide.

  通过分离曼尼希碱盐酸盐并用氢氧化钾滴定环化，可以避免 2-羟基苯乙酮与甲醛缩合合成 4-苯并吡喃酮的问题。
• Synthesis and reactivity of Mannich bases. Part 15: Synthesis of 3-(2-(1-pyrazolyl)ethyl)-1,2-benzisoxazoles
  作者：Gheorghe Roman、Eugenia Comanita、Bogdan Comanita

  DOI：10.1016/s0040-4020(02)00027-3

  日期：2002.2

  new Mannich bases derived from ortho-hydroxyacetophenones and containing pyrazoles as amine moieties have been subjected to oximation in alkaline medium. The selective acetylation to the oximino hydroxyl of the resulting oximes led to the corresponding oxime-acetates. These have been transformed via a ring closure reaction in refluxing benzene and in the presence of anhydrous K2CO3 into 3-(2-(1-pyrazolyl)ethyl)-1

  四种从邻羟基苯乙酮衍生并含有吡唑作为胺基的新曼尼希碱已在碱性介质中进行了肟化反应。所得肟的肟基肟的选择性乙酰化反应生成相应的肟乙酸酯。这些已通过在回流的苯中的闭环反应并在无水K 2 CO 3的存在下转化成3-（2-（1-吡唑基）乙基）-1，2-苯并恶唑，其作为潜在的药理学相关化合物是有价值的。