1-{4-hydroxy-3-[(morpholin-4-yl)methyl]phenyl}ethan-1-one | 92041-43-5

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 1-{4-hydroxy-3-[(morpholin-4-yl)methyl]phenyl}ethan-1-one
• 英文别名: 1-(4-hydroxy-3-(N-morpholinyl)methylphenyl)ethanone；1-[4-hydroxy-3-(morpholinomethyl)phenyl]ethanone；1-(4-hydroxy-3-morpholin-4-ylmethyl-phenyl)-ethanone；4-Hydroxy-3-morpholinomethyl-acetophenon；1-[4-Hydroxy-3-(morpholin-4-ylmethyl)phenyl]ethan-1-one；1-[4-hydroxy-3-(morpholin-4-ylmethyl)phenyl]ethanone
• CAS: 92041-43-5
• 化学式: C₁₃H₁₇NO₃
• mdl: MFCD06357371
• 分子量: 235.283
• InChiKey: KIONGQRFDUEFMS-UHFFFAOYSA-N

物化性质

• 熔点：
  67-68 °C
• 沸点：
  411.1±45.0 °C(Predicted)
• 密度：
  1.195±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.7
• 重原子数：
  17
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.461
• 拓扑面积：
  49.8
• 氢给体数：
  1
• 氢受体数：
  4

安全信息

• 海关编码：
  2934999090

反应信息

• 作为反应物：
  描述：

  5-甲基呋喃醛 、 1-{4-hydroxy-3-[(morpholin-4-yl)methyl]phenyl}ethan-1-one 在 氢氧化钾 作用下， 以 甲醇 、 水 为溶剂， 反应 24.0h， 以70%的产率得到(E)-1-[4-hydroxy-3-(morpholinomethyl)phenyl]-3-(5-methylfuran-2-yl)prop-2-en-1-one
  参考文献：
  名称：

  Design, synthesis, and biological evaluation of Mannich bases of heterocyclic chalcone analogs as cytotoxic agents

  摘要：

  The chalcone skeleton (1,3-diphenyl-2-propen-1-one) is a unique template that is associated with various biological activities. We synthesized Mannich bases of heterocyclic chalcones (9-47) using a one-step Claisen-Schmidt condensation of heterocyclic aldehydes with Mannich bases of acetophenones, and tested the target compounds for cytotoxicity against three human cancer cell lines (prostate, PC-3; breast, MCF-7; nasopharynx, KB) and a multi-drug resistant subline (KB-VIN). Out of the 39 chalcones synthesized, 31 compounds showed potent activity against at least one cell line with IC50 values ranging from 0.03 to 3.80 mu g/mL. Structure-activity relationships (SAR) are also discussed. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2008.06.018
• 作为产物：
  描述：

  吗啉 、 3’-氯甲基-4’-羟基苯乙酮 以 苯 为溶剂， 反应 5.0h， 以96%的产率得到1-{4-hydroxy-3-[(morpholin-4-yl)methyl]phenyl}ethan-1-one
  参考文献：
  名称：

  Borthakur, R. C.; Borthakur, N.; Rastogi, R. C., Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 1984, vol. 23, # 3, p. 244 - 248

  摘要：

  DOI：

文献信息

• Cu(II)-Catalyzed <i>ortho</i>-Selective Aminomethylation of Phenols
  作者：Jin-Ling Dai、Nan-Qi Shao、Jin Zhang、Run-Ping Jia、Dong-Hui Wang

  DOI：10.1021/jacs.7b06785

  日期：2017.9.13

  A Cu(II)-catalyzed ortho-selective functionalization of free phenols with trifluoroborates to afford Csp2-Csp3 coupling products under mild conditions has been developed. A variety of functional groups on the phenol and the potassium aminomethyltrifluoroborate substrates were found compatible, furnishing the corresponding products in moderate to excellent yields. A single-electron transfer radical

  已经开发出一种 Cu(II) 催化的游离酚与三氟硼酸盐的邻位选择性官能化，以在温和条件下提供 Csp2-Csp3 偶联产物。发现苯酚和氨基甲基三氟硼酸钾底物上的各种官能团是相容的，以中等至极好的收率提供相应的产品。提出了一种涉及六元过渡态的单电子转移自由基偶联机制，以合理化反应中的高水平邻位选择性。该协议提供了对邻氨基甲基取代酚、非天然氨基酸和其他生物活性小分子的直接访问。
• Microwave-Assisted Synthesis of Mono- and Disubstituted 4-Hydroxyacetophenone Derivatives via Mannich Reaction: Synthesis, XRD and HS-Analysis
  作者：Ghadah Aljohani、Musa Said、Dieter Lentz、Norazah Basar、Arwa Albar、Shaya Alraqa、Adeeb Ali

  DOI：10.3390/molecules24030590

  日期：——

  reaction takes a short time and is non-catalyzed and reproducible on a gram scale. The environmentally benign methodology provides a novel alternative, to the conventional methodologies, for the synthesis of mono- and disubstituted Mannich bases of 4-hydroxyacetophenone. All compounds were well-characterized by FT-IR, 1H NMR, 13C NMR, and mass spectrometry. The structures of 1-4-hydroxy-3-[(morpholin

  通过区域选择性取代反应，从 4-羟基苯乙酮和不同的仲胺以定量产率开发了一种高效的微波辅助一步合成曼尼希碱的路线。该反应需要很短的时间，并且是非催化的，可在克规模上重现。环境友好的方法为合成 4-羟基苯乙酮的单取代和双取代曼尼希碱的传统方法提供了一种新的替代方法。所有化合物均通过 FT-IR、1H NMR、13C NMR 和质谱法进行了充分表征。1-4-羟基-3-[(morpholin-4-yl)methyl]phenyl}ethan-1-one (2a) 和 1-4-hydroxy-3-[(pyrrolidin-1-yl) 的结构甲基]苯基}乙烷-1-one (3a) 通过单晶 X 射线晶体学测定。化合物 2a 和 3a 以单斜晶系、P21/n 和斜方晶系结晶，分别为 Pbca。2a分子结构最典型的特征是吗啉片断采用分子内氢键强的椅式构象。化合物 3a 也表现出分子间氢键。此外，计算的
• Gautier,J.-A. et al., Comptes Rendus Hebdomadaires des Seances de l'Academie des Sciences, 1964, vol. 258, p. 3731 - 3734
  作者：Gautier,J.-A. et al.

  DOI：——

  日期：——
• Design, synthesis, ADME characterization and antileishmanial evaluation of novel substituted quinoline analogs
  作者：Vadiraj S. Gopinath、Mukkavilli Rao、Rahul Shivahare、Preeti Vishwakarma、Sweta Ghose、Ashok Pradhan、Ramamohan Hindupur、Koushik Das Sarma、Suman Gupta、Sunil K. Puri、Delphine Launay、Denis Martin

  DOI：10.1016/j.bmcl.2014.03.065

  日期：2014.5

  In vitro ADME characterization of the lead compound 1 identified for visceral leishmaniasis was undertaken and further structural analogs were synthesized for antileishmanial screening. Compound 1 was highly permeable in intestinal PAMPA model (31 x 10(-6) cm/s) and was moderately bound to mouse and human plasma proteins (% bound 85-95%), its blood to plasma concentration ratio was less than 1, but the compound was unstable in blood. Compound 1 was found to have no CYP450 liability with CYP2C9, 2C19, 2D6 and 3A4. It showed inhibition with CYP1A2 with an IC50 value of 0.50 mu M. Analogs of 1 were synthesized and subsequently characterized for in vitro activity against the intracellular form of Leishmania donovani. Resulting quinolines were found to have similar efficacy as 1 against the parasite. Compounds 8b and 8f were found to be the most active with IC50 values of 0.84 mu M and 0.17 mu M, respectively compared to 0.22 mu M for compound 1. Of all the analogs tested, 8d was stable in hamster, mouse and human liver microsomes but lost the efficacy with an IC50 of 6.42 mu M. Based on the in vitro efficacy and DMPK profile, compounds 8b and 8f seem the best candidates to be screened in further assays. (C) 2014 Elsevier Ltd. All rights reserved.
• BORTHAKUR, R. C.;BORTHAKUR, N.;RASTOGI, R. C., INDIAN J. CHEM., 1984, 23, N 3, 244-248
  作者：BORTHAKUR, R. C.、BORTHAKUR, N.、RASTOGI, R. C.

  DOI：——

  日期：——