4-(dimethylamino)-N,N-diethylbenzamide | 95725-07-8

• 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: 4-(dimethylamino)-N,N-diethylbenzamide
• 英文别名: N,N-diethyl 4-(N',N'-dimethylamino)benzamide
• CAS: 95725-07-8
• 化学式: C₁₃H₂₀N₂O
• mdl: MFCD01216757
• 分子量: 220.315
• InChiKey: RAYAQSJSJHVBED-UHFFFAOYSA-N

物化性质

• 熔点：
  72-73 °C
• 沸点：
  367.6±25.0 °C(Predicted)
• 密度：
  1.021±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  16
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.461
• 拓扑面积：
  23.6
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  4-(dimethylamino)-N,N-diethylbenzamide 在 叔丁基锂 、 二苯基二硒醚 作用下， 以 四氢呋喃 、 正戊烷 为溶剂， 反应 0.5h， 以75%的产率得到2,6-bis(dimethylamino)-9,10-anthraquinone
  参考文献：
  名称：

  Selenoxanthones via Directed Metalations in 2-Arylselenobenzamide Derivatives

  摘要：

  The reaction of N, N-diethyl 4-(N, N-dimethyl-amino)-2-phenylselenobenzamide (7a), N, N-diethyl 4-methoxy-2-phenylselenobenzamide (7b), N, N-diethyl 4-(N, N'-dimethylamino)-2-[(3-(N, N-dimethylamino)phenylseleno]benzamide (7c), and N, N-diethyl 4-methoxy-2-(3-methoxy-phenylseleno)-benzamide (7d) with excess lithium diisopropylamide (LDA) gave 2-N, N-(dimethylamino)-9H-selenoxanthone (9a), 2-methoxy-9H-selenoxanthone (9b), 2,7-bis-N, N-(dimethylamino)-9H-selenoxanthone (9c), and 2,5-dimethoxy-9H-selenoxanthone (9d) in 70%, 59% 23%, and 90% isolated yields, respectively. N, N-Diethyl 2-phenylselenobenzamide (2-Se) gave no reaction with LDA, t-BuLi, MeLi, or lithium 2,2,6,6-tetramethylpiperidide as base. Electron donation from the 4-substituent of benzamide derivatives 7a-7d may increase the directing ability of the carbonyl oxygen to metalate the 2-position of the arylseleno group.

  DOI：

  10.1021/jo026635t
• 作为产物：
  描述：

  4-二甲氨基苯甲酸 在 氯化亚砜 作用下， 以 二氯甲烷 为溶剂， 反应 3.0h， 生成 4-(dimethylamino)-N,N-diethylbenzamide
  参考文献：
  名称：

  Selenoxanthones via Directed Metalations in 2-Arylselenobenzamide Derivatives

  摘要：

  The reaction of N, N-diethyl 4-(N, N-dimethyl-amino)-2-phenylselenobenzamide (7a), N, N-diethyl 4-methoxy-2-phenylselenobenzamide (7b), N, N-diethyl 4-(N, N'-dimethylamino)-2-[(3-(N, N-dimethylamino)phenylseleno]benzamide (7c), and N, N-diethyl 4-methoxy-2-(3-methoxy-phenylseleno)-benzamide (7d) with excess lithium diisopropylamide (LDA) gave 2-N, N-(dimethylamino)-9H-selenoxanthone (9a), 2-methoxy-9H-selenoxanthone (9b), 2,7-bis-N, N-(dimethylamino)-9H-selenoxanthone (9c), and 2,5-dimethoxy-9H-selenoxanthone (9d) in 70%, 59% 23%, and 90% isolated yields, respectively. N, N-Diethyl 2-phenylselenobenzamide (2-Se) gave no reaction with LDA, t-BuLi, MeLi, or lithium 2,2,6,6-tetramethylpiperidide as base. Electron donation from the 4-substituent of benzamide derivatives 7a-7d may increase the directing ability of the carbonyl oxygen to metalate the 2-position of the arylseleno group.

  DOI：

  10.1021/jo026635t

文献信息

• Clickable coupling of carboxylic acids and amines at room temperature mediated by SO₂F₂: a significant breakthrough for the construction of amides and peptide linkages
  作者：Shi-Meng Wang、Chuang Zhao、Xu Zhang、Hua-Li Qin

  DOI：10.1039/c9ob00699k

  日期：——

  carboxylic acids with amines was developed for the synthesis of a broad scope of amides in a simple, mild, highly efficient, robust and practical manner (>110 examples, >90% yields in most cases). The direct click reactions of acids and amines on a gram scale are also demonstrated using an extremely easy work-up and purification process of washing with 1 M aqueous HCl to provide the desired amides in

  酰胺键和肽键的构建是所有生命过程和有机合成中最基本的转变之一。结构无处不在的酰胺基序的合成对于许多重要分子（如肽，蛋白质，生物碱，药剂，聚合物，配体和农用化学品）的组装至关重要。开发了一种SO2F2介导的羧酸与胺的直接可点击偶合方法，以简单，温和，高效，稳健和实用的方式合成各种酰胺（> 110例，大多数情况下> 90％的收率） ）。
• A BEt₃-Base Catalyst for Amide Reduction with Silane
  作者：Wubing Yao、Huaquan Fang、Qiaoxing He、Dongjie Peng、Guixia Liu、Zheng Huang

  DOI：10.1021/acs.joc.9b00277

  日期：2019.5.17

  herein is the development of a simple but practical catalytic system for the selective reduction of amides with hydrosilane or hydrosiloxane. Low-cost and readily available triethylborane (1.0 M in THF), in combination with a catalytic amount of an alkali metal base, was found to catalyze the reduction of all three amide classes (tertiary, secondary, and primary amides) to form amines under mild conditions

  本文报道了一种简单但实用的催化体系的开发，该体系用于用氢硅烷或氢硅氧烷选择性还原酰胺。发现低成本且易于获得的三乙基硼烷（在THF中为1.0 M）与催化量的碱金属碱结合，可催化所有三种酰胺类别（叔，仲和伯酰胺）的还原反应，从而在室温下形成胺。温和的条件。另外，还可以通过使用BEt 3和碱的适当组合来实现将仲酰胺选择性转化为醛亚胺和将伯酰胺选择性转化为腈。这些赌注3的范围碱催化的酰胺氢化硅烷化反应已被深入研究。机理研究的初步结果表明，经过改进的Piers硅烷Si–H···B活化方式，其中BEt 3提取氢化物的过程是通过烷氧基或氢氧根阴离子与Si中心的配位来促进的。
• Palladium-Catalyzed N-Acylation of Tertiary Amines by Carboxylic Acids: A Method for the Synthesis of Amides
  作者：Zhaohui Li、Long Liu、Kaiqiang Xu、Tianzeng Huang、Xinyi Li、Bin Song、Tieqiao Chen

  DOI：10.1021/acs.orglett.0c01869

  日期：2020.7.17

  A palladium-catalyzed N-acylation of tertiary amines by carboxylic acids was achieved through C–N cleavage. This reaction showed a wide substrate scope. Both aromatic and aliphatic acids served well as the acylating reagents and coupled with tertiary amines to produce the corresponding amides in good to excellent yields. With the strategy, bioactive carboxylic acids were also efficiently modified,

  通过C–N裂解，实现了羧酸对钯催化的叔胺的N-酰化反应。该反应显示出较宽的底物范围。芳族和脂族酸都很好地用作酰化剂，并与叔胺偶联以良好或优异的产率产生相应的酰胺。通过该策略，还可以有效地修饰生物活性羧酸，从而突出了该方法在有机合成中的合成价值。
• Conversion of Thioamides into Their Corresponding Oxygen Analogues Using Silver Carbonate Supported on Celite
  作者：B. Movassagh、M. M. Lakouraj、A. Gholami

  DOI：10.1080/10426500390228620

  日期：2003.9.1

  Silver carbonate supported on celite (Ag2CO3/Celite) is used as a mild heterogeneous reagent for conversion of variety of thioamides into their corresponding amides in acetonitrile at room temperature. We thank the Razi University Research Council for financial assistance.

  硅藻土 (Ag2CO3/Celite) 上负载的碳酸银用作温和的非均相试剂，用于在室温下将各种硫代酰胺在乙腈中转化为相应的酰胺。我们感谢拉齐大学研究委员会的财政援助。
• Titanocene-Catalyzed Coupling of Aromatic Amides in the Presence of Organosilanes:  A Novel Route to Vicinal Diamines and a New Class of Amine-Substituted Oligomers
  作者：Kesamreddy Rangareddy、Kumaravel Selvakumar、John. F. Harrod

  DOI：10.1021/jo049220b

  日期：2004.10.1

  starting materials, and in high yields. In addition, the coupling of 1,4- and 1,3-bis-(N,N,N‘,N‘-tetraalkyl)arylenediamides is shown, under the same experimental conditions, to yield oligomers: R2NC(O)C6H4CH(NR2)-[CH(NR2)C6H4CH(NR2)]n-CH(NR2)C6H4C(O)-NR2 (R = methyl and ethyl; n = 0 to ca. 5). The chemical structures of these unprecedented oligomers are determined by comparison of NMR and MS spectra to

  已经针对多种具有不同取代模式的底物对标题反应进行了调查。除少数例外，该方法可从广泛获得的廉价原料中一锅法合成1,2-二胺。此外，1,4-和1,3-双-耦合器（Ñ，Ñ，Ñ “ Ñ ” -tetraalkyl）arylenediamides所示，在相同的实验条件下，得到低聚物，R 2 NC（O） C 6 H 4 CH（NR 2）-[CH（NR 2）C 6 H 4 CH（NR 2）] n -CH（NR 2）C 6 H 4 C（O）-NR 2（R ＝甲基和乙基；n＝ 0至约5）。通过将NMR和MS光谱与由类似的N，N-二烷基苯甲酰胺制备的邻位二胺的化学光谱进行比较，可以确定这些前所未有的低聚物的化学结构。限制低聚物链长的根源可能是由于内部苄基胺基团的特殊作用，因为发现底物4-Me 2 NCH 2 C 6 H 4 C（O）NMe 2与另一个4-取代的N，N研究了-二烷基苯甲酰胺。简要研究了N-甲基邻