3-dimethylaminomethyl-4-hydroxyacetophenone | 73096-98-7

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 3-dimethylaminomethyl-4-hydroxyacetophenone
• 英文别名: 4-Hydroxy-3-dimethylaminomethyl-acetophenon；1-[3-[(Dimethylamino)methyl]-4-hydroxyphenyl]ethanone
• CAS: 73096-98-7
• 化学式: C₁₁H₁₅NO₂
• 分子量: 193.246
• InChiKey: WAENDPRPZPEBQR-UHFFFAOYSA-N

物化性质

• 熔点：
  72 °C(Solv: ligroine (8032-32-4))
• 沸点：
  328.7±32.0 °C(Predicted)
• 密度：
  1.098±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.1
• 重原子数：
  14
• 可旋转键数：
  3
• 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：
  1
• 氢受体数：
  3

安全信息

• 储存条件：
  室温

反应信息

• 作为反应物：
  描述：

  3-dimethylaminomethyl-4-hydroxyacetophenone 、 O,O-二乙基硫代磷酰氯 在 potassium carbonate 作用下， 以 丙酮 为溶剂， 反应 4.0h， 以70%的产率得到1-[4-diethoxyphosphinothioyloxy-3-[(dimethylamino)methyl]phenyl]ethanone
  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：
• 作为产物：
  描述：

  n,n-二甲基亚甲基碘化胺 、 对羟基苯乙酮 在 potassium carbonate 作用下， 以 二氯甲烷 为溶剂， 反应 7.0h， 以85%的产率得到3-dimethylaminomethyl-4-hydroxyacetophenone
  参考文献：
  名称：

  Selective Synthesis of Phenolic Mannich Bases under Solid-Liquid Phase Transfer Conditions

  摘要：

  DOI：

  10.1055/s-1983-30560

文献信息

• An Inverse Electron Demand Azo-Diels–Alder Reaction of <i>o</i>-Quinone Methides and Imino Ethers: Synthesis of Benzocondensed 1,3-Oxazines
  作者：Dmitry V. Osipov、Vitaly A. Osyanin、Guzel’ D. Khaysanova、Elvira R. Masterova、Pavel E. Krasnikov、Yuri N. Klimochkin

  DOI：10.1021/acs.joc.8b00692

  日期：2018.4.20

  the reactions of o-quinone methide precursors with imino ethers. The reaction provides a versatile route to substituted 1,3-benzoxazines. The proposed reaction mechanism involves the generation of the o-quinone methide intermediates, imino-Diels–Alder reaction, and elimination. This cascade process is a rare example of the participation of imino ethers as dienophiles.

  我们已经研究了邻醌甲基化物前体与亚氨基醚的反应。该反应提供了取代的1，3-苯并恶嗪的通用途径。拟议的反应机制涉及邻醌甲基化物中间体的产生，亚氨基-狄尔斯-阿尔德反应和消除。这种级联过程是亚氨基醚作为亲双烯体参与的罕见例子。
• 查尔酮双曼尼希碱类化合物、其制备方法和用途
  申请人：四川大学

  公开号：CN109608346B

  公开（公告）日：2022-04-22

  本发明公开了一类新型的查尔酮双曼尼希碱类化合物（I）及其药学上可接受的盐、其制备方法、药物组合物和在制备治疗和/或预防神经系统相关疾病药物中的用途，包括但不限于血管性痴呆、阿尔茨海默氏病、帕金森氏病、亨廷顿氏病、HIV相关痴呆病、多发性硬化症、肌萎缩侧索硬化症、神经性疼痛、青光眼、缺血性脑卒中、出血性脑卒中、以及脑外伤引起的神经损伤等疾病；
• Synthesis of the β₂ Agonist (<i>R</i>)-Salmeterol Using a Sequence of Supported Reagents and Scavenging Agents
  作者：Robert N. Bream、Steven V. Ley、Panayiotis A. Procopiou

  DOI：10.1021/ol020128g

  日期：2002.10.1

  graphicThe enantioselective synthesis of (R)-salmeterol has been achieved by using a sequence of supported reagents and sequestering agents. The saligenin core was installed by a regiospecific alkylation and a chiral auxiliary approach was employed to introduce the desired stereochemistry via a diastereoselective reduction.
• Dimmock; Erciyas; Kirkpatrick, Pharmazie, 1988, vol. 43, # 9, p. 614 - 616
  作者：Dimmock、Erciyas、Kirkpatrick、King

  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.