N,N-diethyl-2,5-dimethylbenzamide | 26906-15-0

• 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: N,N-diethyl-2,5-dimethylbenzamide
• 英文别名: N,N-Diethyl-2,5-dimethylbenzamid
• CAS: 26906-15-0
• 化学式: C₁₃H₁₉NO
• mdl: MFCD20142413
• 分子量: 205.3
• InChiKey: TWXANGNDDHVUIU-UHFFFAOYSA-N

物化性质

• 沸点：
  108-115 °C(Press: 1 Torr)
• 密度：
  0.9869 g/cm3

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  15
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.461
• 拓扑面积：
  20.3
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  N,N-diethyl-2,5-dimethylbenzamide 在 正丁基锂 、 四甲基乙二胺 、 仲丁基锂 、 臭氧 、 鹰爪豆碱 作用下， 以 四氢呋喃 、 甲醇 、 正己烷 、 环己烷 、 甲苯 为溶剂， 反应 6.5h， 生成 (-)-N,N-diethyl-2-(1-allyl)ethyl-5-methylbenzamide
  参考文献：
  名称：

  Novel Sparteine-Mediated Enantio-Dichotomic Formal Synthesis of (R)-(−)- and (S)-(+)-Curcuphenol

  摘要：

  High and opposite enantiodiscriminations were observed between tertiary amides and secondary amides in the sparteine-mediated lateral metalation-allylation of 2-ethyl-m-toluamide derivatives (2a, 2e), The results described above have been applied for the formal synthesis of both enantiomers of curcuphenol. The brief mechanistic studies suggested that stereoinformation was introduced after the deprotonation step.

  DOI：

  10.1021/jo001485c
• 作为产物：
  描述：

  2,5-二甲基苯甲酸 在 氯化亚砜 作用下， 以 二氯甲烷 为溶剂， 生成 N,N-diethyl-2,5-dimethylbenzamide
  参考文献：
  名称：

  通过Vilsmeier-Haack反应合成12-氧代苯并[ c ]菲啶酮和4-取代的3-芳基异喹啉酮

  摘要：

  在3-芳基异喹啉酮上进行Vilsmeier-Haack反应后，得到了多种多样的4-甲酰基化的3-芳基异喹啉酮，这些衍生物进一步衍生为12-氧代苯并[ c ]菲啶酮，4-烷氧基甲基-3-芳基异喹啉酮，3-芳基-4-苯氧基甲基异喹啉酮，4-氨基甲基- 3-芳基喹诺酮和3-异喹啉基-2-苯基-丙烯腈的合成策略不同。

  DOI：

  10.1016/j.tet.2011.10.053

文献信息

• 5, 6, or 7-Substituted - 3-(hetero) arylisoquinolinamine derivatives and therapeutic use thereof
  申请人：Lee Young B.

  公开号：US20080182871A1

  公开（公告）日：2008-07-31

  The present invention relates to 5, 6, or 7-substituted-3-(hetero)arylisoquinolinamine derivatives represented by general formula D, their pharmacologically acceptable salts thereof, and compositions containing such compounds. Methods for treating hyperproliferative disorders by administering the compounds are also included.

  本发明涉及一般公式D所代表的5,6或7-取代-3-(杂)芳基异喹啉胺衍生物及其药理学上可接受的盐，以及含有这类化合物的组合物。还包括通过给予这些化合物来治疗过度增殖性疾病的方法。
• α-C–H/N–H Annulation of Alicyclic Amines via Transient Imines: Preparation of Polycyclic Lactams
  作者：Weijie Chen、Daniel Seidel

  DOI：10.1021/acs.orglett.1c01125

  日期：2021.5.7

  Polycyclic lactams are prepared in a single operation from o-toluamides and cyclic amines in a process that involves transient cyclic imines, species that are conveniently obtained in situ from the corresponding lithium amides and simple ketone oxidants. Imines thus generated, such as 1-pyrroline and 1-piperideine, engage lithiated o-toluamides in a facile annulation process. Undesired side reactions

  多环内酰胺是由邻甲苯酰胺和环状胺在单一操作中制备的，该过程涉及瞬态环状亚胺，该物质可以方便地从相应的氨基锂和简单的酮氧化剂原位获得。由此产生的亚胺，例如1-吡咯啉和1-哌啶，在轻松的成环过程中与锂化邻甲苯酰胺结合。通过明智地选择反应条件，可以抑制不需要的副反应，例如亚胺去质子化和邻甲苯酰胺二聚化。
• FUSED HETEROCYCLIC COMPOUND AND MEDICINAL USE THEREOF
  申请人：Mitsubishi Pharma Corporation

  公开号：EP1396488A1

  公开（公告）日：2004-03-10

  The fused heterocyclic compound of the present invention, which is represented by the formula (I): wherein each symbol is as defined in the specification, an optically active form thereof, a pharmaceutically acceptable salt thereof, a hydrate thereof and a water adduct thereof show poly(ADP-ribose) synthase inhibitory action and are useful as therapeutic drugs for cerebral infarction.

  本发明的融合杂环化合物，其化学式表示为（I）：其中每个符号如规范中定义，其光学活性形式，其药学上可接受的盐，其水合物和水加合物显示聚(ADP-核糖)合酶抑制作用，并可用作治疗脑梗死的药物。
• Synthesis of novel 5-oxaprotoberberines as bioisosteres of protoberberines
  作者：Yifeng Jin、Daulat Bikram Khadka、Su Hui Yang、Chao Zhao、Won-Jea Cho

  DOI：10.1016/j.tetlet.2014.01.020

  日期：2014.2

  5-Oxaprotoberberinones and 5-oxaprotoberberinium were synthesized as bioisosteres of protoberberines. 5-Oxaprotoberberinones were prepared by linking phenol with the isoquinolone ring of 3-phenolisoquinolones by methyleneoxy bridge, while the quaternary 5-oxaprotoberberinium salt was synthesized by reduction and oxidation of the lactam moiety of 5-oxaprotoberberinone.

  合成了5-Oxaprotoberberinones和5-oxaprotoberberinium作为原小ber碱的生物等排体。通过亚甲氧基桥将苯酚与3-苯酚异喹啉酮的异喹诺酮环连接，制得5-氧杂小ino碱酮，而5-氧杂小in碱的内酰胺部分的还原和氧化反应可合成季铵化的5-氧杂小ber碱盐。
• Asymmetric Synthesis of 3-Substituted Dihydro-2<i>H</i>-isoquinolin-1-ones, Dihydro- and Tetrahydroisoquinolines via 1,2-Addition/Ring Closure
  作者：Dieter Enders、Volker Braig、Marine Boudou、Gerhard Raabe

  DOI：10.1055/s-2004-834861

  日期：——

  The asymmetric synthesis of 3-substituted dihydro-2H-isoquinolin-1-ones, dihydro- and tetrahydroisoquinolines is described. The key operation is a tandem 1,2-addition/ring closure sequence employing lithiated ortho-toluamides and aldehyde SAMP-or RAMP-hydrazones as substrates, followed by N-N bond cleavage to remove the auxiliary. Moderate to good yields and high enantiomeric excesses (ee = 85-99%)

  描述了 3-取代二氢-2H-异喹啉-1-酮、二氢和四氢异喹啉的不对称合成。关键操作是串联 1,2-加成/闭环序列，使用锂化邻甲苯酰胺和醛 SAMP-或 RAMP-腙作为底物，然后进行 NN 键断裂以去除辅助剂。达到中等至良好的产率和高对映体过量（ee = 85-99%）。