N,N-diethyl-2-benzoylbenzamide | 3034-28-4

• 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-benzoylbenzamide
• 英文别名: 2-(diethylcarbamoyl)benzophenone；2-benzoyl-N,N-diethylbenzamide；2-benzoyl-benzoic acid diethylamide；2-Benzoyl-benzoesaeure-diaethylamid；Benzamide,2-benzoyl-n,n-diethyl-
• CAS: 3034-28-4
• 化学式: C₁₈H₁₉NO₂
• 分子量: 281.354
• InChiKey: DAFABXKDAVYFER-UHFFFAOYSA-N

物化性质

• 熔点：
  51.5 °C
• 沸点：
  125-130 °C(Press: 0.1 Torr)
• 密度：
  1.099±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  21
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  37.4
• 氢给体数：
  0
• 氢受体数：
  2

安全信息

• 海关编码：
  2924299090

反应信息

• 作为反应物：
  描述：

  N,N-diethyl-2-benzoylbenzamide 在 盐酸 、 sodium tetrahydroborate 作用下， 以 甲醇 为溶剂， 反应 5.0h， 生成 3-苯基苯酞
  参考文献：
  名称：

  Probes for Narcotic Receptor-Mediated Phenomena. 25. Synthesis and Evaluation of N-Alkyl-Substituted (α-Piperazinylbenzyl)benzamides as Novel, Highly Selective δ Opioid Receptor Agonists

  摘要：

  A series of N-alkyl- and N,N-dialkyl-4-[alpha-{(2S,5R)-4-allyl-2,5-dimethyl-1-piperazinyl}benzyl]-benzamides were synthesized and evaluated for binding affinities at mu, delta, and kappa opioid receptor subtypes. Several compounds (2e,f,h,i,m) strongly bound to the delta receptor with IC50 values in the nanomolar range. On the other hand, the binding affinities of these compounds for the mu and kappa receptors were in the micromolar or greater range indicating excellent delta opioid receptor subtype selectivities. In this series, two important structure-activity relationships were found for the delta receptor binding affinity. First, the spatial orientation of the alpha-benzylic position influenced the affinities with the alpha R derivatives 2a-n generally showing more than 10-fold greater affinity than the alpha S derivatives 3a-n. Second, the binding affinities were strongly influenced by the number of alkyl substituents on the amide nitrogen. N-Monoalkylbenzamide derivatives 2b-d showed lower affinity than N,N-dialkylbenzamide derivatives 2e-n, and the N-unsubstituted benzamide derivative 2a had the lowest affinity for the delta receptor in the series. The dramatic effect of the amide group substitution pattern on the binding affinity for the delta receptor strongly suggests that the amide function is an important structural element in the interaction of this series of compounds at the delta receptor. Selective compounds in this series were examined for binding affinity in cloned human mu and delta receptors. The results obtained generally paralleled those from the rat brain binding assay. Compounds 2e,f with potent delta binding affinities and high delta selectivities were shown to be delta agonists with high selectivity by studies in the guinea pig ileum (GPI) and mouse vas deferens (MVD) preparations. Compound 2f was the most selective compound in the rat brain and GPI/MVD assays with 1755- and 958-fold delta vs mu selectivity, respectively.

  DOI：

  10.1021/jm970106d
• 作为产物：
  描述：

  邻苯甲酰苯甲酸 在 氯化亚砜 作用下， 以 四氢呋喃 为溶剂， 反应 2.0h， 生成 N,N-diethyl-2-benzoylbenzamide
  参考文献：
  名称：

  Probes for Narcotic Receptor-Mediated Phenomena. 25. Synthesis and Evaluation of N-Alkyl-Substituted (α-Piperazinylbenzyl)benzamides as Novel, Highly Selective δ Opioid Receptor Agonists

  摘要：

  A series of N-alkyl- and N,N-dialkyl-4-[alpha-{(2S,5R)-4-allyl-2,5-dimethyl-1-piperazinyl}benzyl]-benzamides were synthesized and evaluated for binding affinities at mu, delta, and kappa opioid receptor subtypes. Several compounds (2e,f,h,i,m) strongly bound to the delta receptor with IC50 values in the nanomolar range. On the other hand, the binding affinities of these compounds for the mu and kappa receptors were in the micromolar or greater range indicating excellent delta opioid receptor subtype selectivities. In this series, two important structure-activity relationships were found for the delta receptor binding affinity. First, the spatial orientation of the alpha-benzylic position influenced the affinities with the alpha R derivatives 2a-n generally showing more than 10-fold greater affinity than the alpha S derivatives 3a-n. Second, the binding affinities were strongly influenced by the number of alkyl substituents on the amide nitrogen. N-Monoalkylbenzamide derivatives 2b-d showed lower affinity than N,N-dialkylbenzamide derivatives 2e-n, and the N-unsubstituted benzamide derivative 2a had the lowest affinity for the delta receptor in the series. The dramatic effect of the amide group substitution pattern on the binding affinity for the delta receptor strongly suggests that the amide function is an important structural element in the interaction of this series of compounds at the delta receptor. Selective compounds in this series were examined for binding affinity in cloned human mu and delta receptors. The results obtained generally paralleled those from the rat brain binding assay. Compounds 2e,f with potent delta binding affinities and high delta selectivities were shown to be delta agonists with high selectivity by studies in the guinea pig ileum (GPI) and mouse vas deferens (MVD) preparations. Compound 2f was the most selective compound in the rat brain and GPI/MVD assays with 1755- and 958-fold delta vs mu selectivity, respectively.

  DOI：

  10.1021/jm970106d

文献信息

• Rhodium-Catalyzed Oxidative <i>ortho</i>-Acylation of Benzamides with Aldehydes: Direct Functionalization of the sp² C–H Bond
  作者：Jihye Park、Eonjeong Park、Aejin Kim、Youngil Lee、Ki-Whan Chi、Jong Hwan Kwak、Young Hoon Jung、In Su Kim

  DOI：10.1021/ol201729w

  日期：2011.8.19

  A rhodium-catalyzed oxidative acylation of benzamides with aryl aldehydes via direct sp2 C–H bond cleavage is described. In the presence of [Cp*RhCl2]2, AgSbF6, and silver carbonate as an oxidant, N,N-diethyl benzamides can be effectively carbonylated to yield ortho-acyl benzamides.

  描述了通过直接的sp 2 C–H键裂解，铑催化的苯甲酰胺与芳基醛的氧化酰化反应。在[Cp * RhCl 2 ] 2，AgSbF 6和碳酸银作为氧化剂的存在下，N，N-二乙基苯甲酰胺可以有效地羰基化，生成邻酰基苯甲酰胺。
• A Novel Aromatic Electrophilic Substitution: Acylation of Aromatics with Cyclic Isoimidium Salts to Yield<i>N,N</i>-Disubstituted β-Aroylcarboxamides
  作者：Alexandru R. Balaban、Theodor-Silviu Balaban、Gerhard V. Boyd

  DOI：10.1055/s-1987-28012

  日期：——

  Cyclic isoimidium perchlorates derived from N,N-diethylphthalamic acid and the monomorpholides of succinic and maleic acid react with benezene, toluene or anisole in the presence of aluminium chloride to give the corresponding ß-aroylcarboxamides in moderate yields.

  来源于N,N-二乙基邻苯二甲酸的环状异吡啶高氯酸盐和琥珀酸及马来酸的单吗啉酯在氯化铝存在下与苯、甲苯或 anisole 反应，产生相应的 β-芳酰羧氨基酯，产率适中。
• Rapid synthesis of isoquinolinones by intramolecular coupling of amides and ketones
  作者：Wen-Tao Wei、Yu Liu、Lin-Miao Ye、Rong-Hui Lei、Xue-Jing Zhang、Ming Yan

  DOI：10.1039/c4ob01948b

  日期：——

  Isoquinolinones were prepared in good yieldsviathe intramolecular coupling of amides and ketones in the presence of KOt-Bu/DMF.

  通过在存在KOt-Bu/DMF的情况下，酰胺和酮的分子内偶联反应，制备了优良产率的异喹啉酮。
• A comparison of secondary and tertiary amides as directors of ortho and adjacent benzylic lithiation and of asymmetric induction in ortho lithiated benzamides
  作者：Peter Beak、Anthony Tse、Joel Haawkins、Chin-Wen Chen、Sander Mills

  DOI：10.1016/s0040-4020(01)91916-7

  日期：1983.1

  Comparisons are made between the influence of secondary and tertiary amides on ortho and adjacent benzylic metallations of benzamides. In the intramolecular competition offered by N,N-diethyl-N-ethylterephthalamide (1) the tertiary amide is the more effective director of ortho lithiation, while the secondary amide is better in the intermolecular competitions offered by the pairs N-ethyl-(9): N,N-diethylbenzamide(10)

  比较仲酰胺和叔酰胺对苯甲酰胺的邻位和邻位苄基金属化的影响。在N，N-二乙基-N-乙基对苯二甲酰胺（1）提供的分子内竞争中，叔酰胺是邻位锂化的更有效导向器，而仲酰胺在N-乙基-（9 ）：N，N-二乙基苯甲酰胺（10）和N-异丙基-（11）：N，N-二异丙基苯甲酰胺（12）。在2-异丙基苯甲酰胺25和26中，仲酰胺和叔酰胺都可以直接金属化到酰胺上; 然而，在仲2-乙基和2-甲基苯甲酰胺中发现苄基金属化21和22以及叔2-乙基苯甲酰胺19。注意到19的抗-N-亚甲基的磁性不等价。内硫基（S）-O-甲基-N-苯甲酰亮氨醇（34）与1-萘甲醛-1-d的反应在内酯化后得到3-（1-萘-1-d）-邻苯二甲酸酯与10％对映异构体过量的。通过在环化之前分离非对映异构体，可以以高对映体纯度获得邻苯二甲酰亚胺。对照实验确定观察到的不对称诱导归因于非对映异构过渡态。相应的叔苯甲酰胺在诱导不对称方面无效。为这些观察提供了结构和机械原理。
• Absolute asymmetric synthesis by nucleophilic carbonyl addition using chiral crystals of achiral amides
  作者：Masami Sakamoto、Shuichiro Kobaru、Takashi Mino、Tsutomu Fujita

  DOI：10.1039/b315729f

  日期：——

  Reaction of the chiral crystals of the achiral amides with n-butyllithium in toluene at −80 °C gave optically active alcohols in 17–84% ee.

  在-80 °C下，将手性酰胺晶体与正丁基锂在甲苯中反应，得到光学活性醇，ee值为17-84%。