3-dimethylamino-1-(3-methoxyphenyl)-prop-2-en-1-one | 62041-46-7

• 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-dimethylamino-1-(3-methoxyphenyl)-prop-2-en-1-one
• 英文别名: (Z/E)-3-(dimethylamino)-1-(3-methoxyphenyl)prop-2-en-1-one；3-dimethylamino-1-(3-methoxyphenyl)propenone；3-Dimethylamino-3'-methoxyacrylophenone；3-(dimethylamino)-1-(3-methoxyphenyl)prop-2-en-1-one
• CAS: 62041-46-7
• 化学式: C₁₂H₁₅NO₂
• mdl: MFCD11501639
• 分子量: 205.257
• InChiKey: QBMMITATXZJWDG-UHFFFAOYSA-N

物化性质

• 熔点：
  46-48℃
• 沸点：
  118-120 °C(Press: 0.025 Torr)
• 密度：
  1.050±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  15
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  29.5
• 氢给体数：
  0
• 氢受体数：
  3

安全信息

• 海关编码：
  2922509090

反应信息

• 作为反应物：
  描述：

  3-dimethylamino-1-(3-methoxyphenyl)-prop-2-en-1-one 在 三乙烯二胺 、 potassium hydroxide 作用下， 以 乙醇 、 水 、 N,N-二甲基甲酰胺 为溶剂， 生成 Ethyl 3-amino-6-(3-methoxyphenyl)thieno[2,3-b]pyridine-2-carboxylate
  参考文献：
  名称：

  Synthesis, preliminary structure–activity relationships, and in vitro biological evaluation of 6-aryl-3-amino-thieno[2,3-b]pyridine derivatives as potential anti-inflammatory agents

  摘要：

  In our previous study, a series of 6-aryl-3-amino-thieno[2,3-b]pyridine derivatives exhibited potent anti-proliferative activities and an unique hepatocellular carcinoma (HCC)-specific anticancer activity was also observed. In further anti-inflammatory research, thienopyridine derivative 1a showed potent inhibition of nitric oxide (NO) production. So a series of thienopyridine analogues of 1a were synthesized and evaluated for anti-inflammatory activities. The structure-activity relationships (SARs) revealed that the most potent analogues 1f and 1o were identified as potent inhibitors of NO production with IC50 values of 3.30 and 3.24 mu M, respectively. These results suggest that these 6-aryl-3-amino-thieno[2,3-b]pyridine derivatives might potentially constitute a novel class of anti-inflammatory agents, which require further studies. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2013.02.059
• 作为产物：
  描述：

  N,N-二甲基甲酰胺二甲基缩醛 、 3-甲氧基苯乙酮 以 1,4-二氧六环 为溶剂， 生成 3-dimethylamino-1-(3-methoxyphenyl)-prop-2-en-1-one
  参考文献：
  名称：

  Rh 催化的烯胺酮和环状 1,3-二羰基化合物的 C–H 活化/环化：获得异香豆素

  摘要：

  通过铑 (III) 催化的 C-H 键活化和烯胺酮和环状 1,3-二羰基化合物的分子内 C-C 级联环化，可以轻松获得异香豆素。合成方案具有广泛的底物范围，具有高官能团耐受性、温和的反应条件和烯胺酮 C-C 键的选择性裂解。值得注意的是，环状 1,3-二羰基化合物可以原位生成碘鎓叶立德作为卡宾前体，通过与 PhI(OAc) 2反应制备多环支架。还举例说明了该方法在制备有用的合成前体和生物活性骨架方面的应用。

  DOI：

  10.1021/acs.joc.2c02898

文献信息

• 6-N-Linked Heterocycle-Substituted 2,3,4,5-Tetrahydro-1H-Benzo[d]Azepines as 5-Ht2c Receptor Agonists
  申请人：Briner Karin

  公开号：US20080214520A1

  公开（公告）日：2008-09-04

  The present invention provides 6-substituted 2,3,4,5-tetrahydro-1H-benzo[d]azepines of Formula I as selective 5-HT 2C receptor agonists for the treatment of 5-HT 2C associated disorders including obesity, obsessive/compulsive disorder, depression, and anxiety: Formula (I) where: R 6 is selected from the group consisting of (a, b, c, d, e) and other substituents are as defined in the specification.

  本发明提供了Formula I的6-取代的2,3,4,5-四氢-1H-苯并[d]氮杂环庚烯作为选择性5-HT2C受体激动剂，用于治疗与5-HT2C相关的疾病，包括肥胖症、强迫症、抑郁症和焦虑症：Formula (I)其中：R6选自(a、b、c、d、e)等基团组成的群，其他取代基如规范中定义。
• Iodine-mediated synthesis of sulfur-bridged enaminones and chromones via double C(sp²)–H thiolation
  作者：Yong Gao、Li Wei、Yunyun Liu、Jie-Ping Wan

  DOI：10.1039/c7ob00619e

  日期：——

  reactions of various enaminones with elemental sulfur giving rise to both sulfur-bridged enaminones and chromones have been realized via iodine promotion. All products were furnished by means of double C(sp2)–H bond thiolation without using any metal catalyst or sensitive oxidant, providing a simple and efficient protocol for the synthesis of diverse sulfur derivatives of enaminones.

  通过碘的促进已经实现了各种烯胺酮与元素硫的反应，其同时引起硫桥联的烯胺酮和色酮。所有产品均通过双C（sp 2）-H键硫醇化而无需使用任何金属催化剂或敏感氧化剂即可提供，为合成烯胺酮的多种硫衍生物提供了简单有效的方案。
• DERIVATIVES OF MACROCYCLIC N-ARYL-2-AMINO-4-ARYL-PYRIMIDINE POLYETHERS AS INHIBITORS OF FTL3 AND JAK
  申请人：PIERRE FABRE MEDICAMENT

  公开号：US20170281622A1

  公开（公告）日：2017-10-05

  The present invention relates to a compound with the following formula: formula (I) or a salt and/or a pharmaceutically acceptable solvate thereof, in particular for use as a drug, in particular in the treatment of cancer, as well as to the pharmaceutical compositions that contain same and to the methods for preparing same.

  本发明涉及具有以下式的化合物：式（I）或其盐和/或药用可接受的溶剂化合物，特别用作药物，特别用于治疗癌症，以及含有相同化合物的药物组合物和制备相同化合物的方法。
• Harnessing Stereospecific <i>Z</i>-Enamides through Silver-Free Cp*Rh(III) Catalysis by Using Isoxazoles as Masked Electrophiles
  作者：Suvankar Debbarma、Sourav Sekhar Bera、Modhu Sudan Maji

  DOI：10.1021/acs.orglett.8b04130

  日期：2019.2.1

  The stereospecific synthesis of Z-enamides is described in this paper. For the first time, isoxazoles have been employed as electrophiles in C–H functionalization to afford thermodynamically less stable Z-enamides utilizing salicylaldehydes in an atom- and step-economic fashion. The stereochemistry of enamides might originate from the relative disposition of atoms present in isoxazole and the intramolecular

  本文描述了Z-烯酰胺的立体有择合成。首次将异恶唑用作C–H功能化过程中的亲电子试剂，从而以原子经济和分步经济的方式利用水杨醛提供热力学上较不稳定的Z-酰胺。烯酰胺的立体化学可能源自异恶唑中存在的原子的相对位置和分子内氢键。由于多种结构上和电子上不同的水杨醛和异恶唑能有效反应，因此该反应显示出极好的范围。
• Design, synthesis, and preliminary bioactivity evaluation of <i>N</i> -benzylpyrimidin-2-amine derivatives as novel histone deacetylase inhibitor
  作者：Yi Zhou、Yanyan Dun、Huansheng Fu、Lei Wang、Xiaole Pan、Xinying Yang、Hao Fang

  DOI：10.1111/cbdd.13019

  日期：2017.11

  Histone deacetylase inhibitors have been identified for the treatment of cancer. Lately, we designed and synthesized a series of substituted N-benzylpyrimidin-2-amine derivatives as potent HDAC inhibitors. Target compounds 6a, 6d, 8a, 8c, and 8f not only exhibited almost equally enzymatic inhibitory activity with SAHA, but showed better antiproliferative activities.

  已经鉴定出组蛋白脱乙酰基酶抑制剂可用于治疗癌症。最近，我们设计并合成了一系列取代的N-苄基嘧啶-2-胺衍生物作为有效的HDAC抑制剂。目标化合物6a，6d，8a，8c和8f不仅表现出与SAHA几乎相同的酶抑制活性，而且表现出更好的抗增殖活性。