2-(dimethylaminomethyl)acetophenone | 40337-69-7

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2-(dimethylaminomethyl)acetophenone
• 英文别名: 2-N,N-dimethylaminomethylacetophenone；2-<(dimethylamino)methyl>acetophenone；o-Dimethylaminomethyl-acetophenon；1-(2-Dimethylaminomethyl-phenyl)-ethanone；1-[2-[(dimethylamino)methyl]phenyl]ethanone
• CAS: 40337-69-7
• 化学式: C₁₁H₁₅NO
• 分子量: 177.246
• InChiKey: VOTVPCCSKDXMMR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  13
• 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：
  20.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  2-(dimethylaminomethyl)acetophenone 在 sodium hydroxide 、 copper(l) iodide 作用下， 以 四氢呋喃 、 乙醇 为溶剂， 反应 2.25h， 生成 3-(2,4-dichlorophenyl)-1-(2-((dimethylamino)methyl)phenyl)pentan-1-one
  参考文献：
  名称：

  Antimalarial and Antiplasmodial Activities of Norneolignans. Syntheses and SAR

  摘要：

  A systematic change of the substituents and side chain of the norneolignan hinokiresinol afforded a 10 fold improvement of the IC50 value toward inhibition of the growth of Plasmodium falciparum. The more potent compounds controlled the parasiterma in mice infected with Plasinodium berghei.

  DOI：

  10.1021/jm0508235
• 作为产物：
  描述：

  1-苯基-1-三甲基硅氧乙烯 、 n,n-二甲基亚甲基碘化胺 以 二氯甲烷 为溶剂， 以66%的产率得到2-(dimethylaminomethyl)acetophenone
  参考文献：
  名称：

  甲硅烷基烯醇醚的-丁基二甲基甲硅烷基在与二甲基（亚甲基）碘化铵反应中的存活率。含氨基的-丁基二甲基甲硅烷基烯醇醚的区域选择性合成。

  摘要：

  通过使丁基丁基二甲基甲硅烷基烯醇醚与二甲基（亚甲基）碘化铵（埃森莫瑟盐）反应，可以以较高的收率（70-90％）获得含氨基的丁基丁基二甲基甲硅烷基烯醇醚。

  DOI：

  10.1016/s0040-4039(01)91296-1

文献信息

• A new regiospecific synthesis of aryl ketones from palladocycles
  作者：R.A. Holton、K.J. Natalie

  DOI：10.1016/0040-4039(81)80072-x

  日期：1981.1

  Aromatic palladocycles undergo facile reaction with acid halides to reglospecifically provide aryl ketones In high yield.

  芳香族帕拉多环与酰卤易于反应，从而以高收率再配位性地提供芳基酮。
• The unexpected formation of a lithium-enolate from bis2-[(dimethylamino)methyl]phenyl copper lithium. X-ray structure of Li4[OC(CH2)C6H4CH2NMe2-2]4
  作者：Johann T.B.H. Jastrzebski、Gerard Van Koten、Martin J.N. Christophersen、Casper H. Stam

  DOI：10.1016/0022-328x(85)80217-5

  日期：1985.9

  Attempted crystallization of the bis(aryl)lithium cuprate, Cu2Li2(C6H4CH2-NMe2-2)4, from diethyl ether/pentane afforded in according to an X-ray diffraction analysis appeared to be the lithium enolate, Li4[OC(=CH2)C6H4CH2NMe2-2]4. This consists of a central Li4O4 cube with intramolecular LiN coordination of the CH2NMe2 substituent. This enolate, which has also been prepared via an independent route

  尝试根据X射线衍射分析从提供的乙醚/戊烷中结晶出双（芳基）锂铜酸铜Cu 2 Li 2（C 6 H 4 CH 2 -NMe 2 -2）4。烯醇盐Li 4 [OC（= CH 2）C 6 H 4 CH 2 NMe 2 -2] 4。它由具有分子内Li 4N配位的CH 2 NMe 2的中心Li 4 O 4立方体组成取代基。该烯醇化物也已经通过独立的途径制备，是结构特征化的烯醇锂的第一个实例，并且包含分子内配位的Li中心。
• Cationic Chalcone Antibiotics. Design, Synthesis, and Mechanism of Action
  作者：Simon F. Nielsen、Mogens Larsen、Thomas Boesen、Kristian Schønning、Hasse Kromann

  DOI：10.1021/jm049424k

  日期：2005.4.1

  This paper describes how the introduction of "cationic" aliphatic amino groups in the chalcone scaffold results in potent antibacterial compounds. It is shown that the most favorable position for the aliphatic amino group is the 2-position of the B-ring, in particular in combination with a lipophilic substituent in the 5-position of the beta-ring. We demonstrate that the compounds act by unselective disruption of cell membranes. Introduction of an additional aliphatic amino group in the A-ring results in compounds that are selective for bacterial membranes combined with a high antibacterial activity against both Gram-positive and -negative pathogens. The most potent compound in this study (78) has an MIC value of 2 mu M against methicillin resistant Staphylococus aureus.
• [EN] AMINO-FUNCTIONAL CHALCONES<br/>[FR] CHALCONES AMINO-FONCTIONNELLES
  申请人：——

  公开号：WO2003097575A3

  公开（公告）日：2004-02-26