N-苄基-N-异丙基苯甲酰胺 | 105680-00-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 中文名称: N-苄基-N-异丙基苯甲酰胺
• 英文名称: N-benzyl-N-isopropylbenzamide
• 英文别名: N-benzyl-N-propan-2-ylbenzamide
• CAS: 105680-00-0
• 化学式: C₁₇H₁₉NO
• mdl: MFCD01212009
• 分子量: 253.344
• InChiKey: YNCVMXHEJUCNJN-UHFFFAOYSA-N

物化性质

• 沸点：
  404.8±24.0 °C(Predicted)
• 密度：
  1.060±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  19
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.235
• 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-苄基-N-异丙基苯甲酰胺 在 lithium aluminium tetrahydride 作用下， 以 乙醚 为溶剂， 反应 5.0h， 生成 N,N-dibenzylisopropylamine
  参考文献：
  名称：

  Stereodynamics of 2-(Diethylamino)propane and 2-(Dibenzylamino)propane. 1H and 13C{1H} DNMR Studies. Molecular Mechanics Calculations

  摘要：

  2-(Diethylamino)propane (DEAP) and 2-(dibenzylamino)propane (DBAP) possess similar molecular symmetries. Interconversion among the stable equilibrium conformations occurs by inversion-rotation at the pyramidal nitrogen and by isolated rotation about-carbon-nitrogen bonds. In DEAF and DBAP, the fact that stable equilibrium conformations cannot have destabilizing syn-1,5 interactions between methyl or phenyl groups limits the number of equilibrium conformations that will be present at concentrations high enough to be NMR detectable. The H-1 and C-13{H-1} NMR spectra of DEAF at 100 K show two diastereomeric pairs of enantiomeric conformations. One pair of enantiomers has the isopropyl methine proton and both ethyl methyl groups gauche to the lone pair (75%). The other pair has the methine proton anti to the lone pair with the ethyl methyl groups respectively gauche and anti to the lone pair (25%). The barrier to inversion-rotation in DEAF (Delta G(double dagger) = 6.4 kcal/mol) is higher than barriers to isolated rotation about carbon-nitrogen bonds (Delta G(double dagger) = 5.3-5.7 kcal/mol). The H-1 and C-13{H-1} NMR spectra of DBAP at 100 K show just one pair of enantiomeric conformations that have the isopropyl methine proton and both phenyl groups gauche to the lone pair. There is no evidence in the NMR spectrum at 100 K for those conformations of DBAP that have a phenyl group anti to the lone pair. The barrier to inversion-rotation in DBAP (Delta G(double dagger) = 6.4 kcal/mol) is higher than the barrier to racemization via isolated rotation about carbon-nitrogen bonds (Delta G(double dagger) = 5.5 kcal/mol). Molecular mechanics calculations of conformational energies are in good agreement with the observed conformational preferences.

  DOI：

  10.1021/ja00155a021
• 作为产物：
  描述：

  苯甲酰溴 在 氢氧化钾 、 lithium aluminium tetrahydride 作用下， 以 乙醚 为溶剂， 反应 40.0h， 生成 N-苄基-N-异丙基苯甲酰胺
  参考文献：
  名称：

  Stereodynamics of 2-(Diethylamino)propane and 2-(Dibenzylamino)propane. 1H and 13C{1H} DNMR Studies. Molecular Mechanics Calculations

  摘要：

  2-(Diethylamino)propane (DEAP) and 2-(dibenzylamino)propane (DBAP) possess similar molecular symmetries. Interconversion among the stable equilibrium conformations occurs by inversion-rotation at the pyramidal nitrogen and by isolated rotation about-carbon-nitrogen bonds. In DEAF and DBAP, the fact that stable equilibrium conformations cannot have destabilizing syn-1,5 interactions between methyl or phenyl groups limits the number of equilibrium conformations that will be present at concentrations high enough to be NMR detectable. The H-1 and C-13{H-1} NMR spectra of DEAF at 100 K show two diastereomeric pairs of enantiomeric conformations. One pair of enantiomers has the isopropyl methine proton and both ethyl methyl groups gauche to the lone pair (75%). The other pair has the methine proton anti to the lone pair with the ethyl methyl groups respectively gauche and anti to the lone pair (25%). The barrier to inversion-rotation in DEAF (Delta G(double dagger) = 6.4 kcal/mol) is higher than barriers to isolated rotation about carbon-nitrogen bonds (Delta G(double dagger) = 5.3-5.7 kcal/mol). The H-1 and C-13{H-1} NMR spectra of DBAP at 100 K show just one pair of enantiomeric conformations that have the isopropyl methine proton and both phenyl groups gauche to the lone pair. There is no evidence in the NMR spectrum at 100 K for those conformations of DBAP that have a phenyl group anti to the lone pair. The barrier to inversion-rotation in DBAP (Delta G(double dagger) = 6.4 kcal/mol) is higher than the barrier to racemization via isolated rotation about carbon-nitrogen bonds (Delta G(double dagger) = 5.5 kcal/mol). Molecular mechanics calculations of conformational energies are in good agreement with the observed conformational preferences.

  DOI：

  10.1021/ja00155a021

文献信息

• Superparamagnetic Fe(OH)₃@Fe₃O₄ Nanoparticles: An Efficient and Recoverable Catalyst for Tandem Oxidative Amidation of Alcohols with Amine Hydrochloride Salts
  作者：Marzban Arefi、Dariush Saberi、Meghdad Karimi、Akbar Heydari

  DOI：10.1021/co5001844

  日期：2015.6.8

  nanoparticles were successfully prepared and characterized. This magnetic nanocomposite was employed as an efficient, reusable, and environmentally benign heterogeneous catalyst for the direct amidation of alcohols with amine hydrochloride salts. Several derivatives of primary, secondary and tertiary amides were synthesized in moderate to good yields in the presence of this catalytic system. The catalyst was

  磁性Fe（OH）3 @Fe 3 O 4纳米粒子的制备和表征成功。该磁性纳米复合材料用作将醇与胺盐酸盐直接酰胺化的有效，可重复使用且对环境无害的多相催化剂。在该催化体系的存在下，以中等至良好的产率合成了伯，仲和叔酰胺的几种衍生物。该催化剂已成功回收利用，最多可重复使用六次，而不会显着降低其催化活性。
• Oxidative amidation by Cu(<scp>ii</scp>)–guanidine acetic acid immobilized on magnetized sawdust with eggshell as a natural base
  作者：Atefeh Darvishi、Maryam Kazemi Miraki、Marzban Arefi、Akbar Heydari

  DOI：10.1039/d0nj00835d

  日期：——

  Copper(II)–guanidine acetic acid complex was immobilized on the surface of magnetized raw waste sawdust (SD) as an abundant natural biopolymer and employed as an efficient and recoverable catalyst in oxidative amidation reaction, while waste eggshell (ES) powder was used as a low-cost solid base. The magnetic raw catalyst was fully characterized using FTIR, XRD, SEM, EDX, TGA, and VSM. A variety of

  铜（II）-胍基乙酸络合物作为丰富的天然生物聚合物固定在磁化的废木屑（SD）表面，可作为氧化酰胺化反应中的一种有效且可回收的催化剂，而废蛋壳（ES）粉末用作低成本的坚实基础。使用FTIR，XRD，SEM，EDX，TGA和VSM对磁性原料催化剂进行了全面表征。使用苄醇和胺盐已成功以中等至高收率成功合成了多种酰胺衍生物。锯末和蛋壳作为两种天然和丰富的废料的应用是本研究的主要优势。而且，这些低成本的催化剂被回收了至少五次，并以最小的活性降低被用于反应系统中。
• Copper-amino group complexes supported on silica-coated magnetite nanoparticles: efficient catalyst for oxidative amidation of methyl arenes
  作者：Meghdad Karimi、Leila Ghandi、Dariush Saberi、Akbar Heydari

  DOI：10.1039/c7nj02257c

  日期：——

  Magnetite nanoparticles coated with mesoporous silica, Fe3O4@SiO2, were prepared. Surface functionalization of this core–shell nanocomposite with (3-aminopropyl)trimethoxysilane (APTMS) followed by its reaction with Cu(OAc)2 was used to develop a new heterogeneous copper complex (Fe3O4@SiO2–APTMS–Cu). The structure and composition of the synthesized nanocatalyst were characterized by FTIR, SEM, VSM

  制备了包覆有介孔二氧化硅Fe 3 O 4 @SiO 2的磁铁矿纳米颗粒。用（3-氨基丙基）三甲氧基硅烷（APTMS）对该核-壳纳米复合材料进行表面功能化，然后使其与Cu（OAc）2反应，用于开发新的异质铜络合物（Fe 3 O 4 @SiO 2–APTMS–Cu）。通过FTIR，SEM，VSM，TEM，XRD和ICP分析对合成的纳米催化剂的结构和组成进行了表征。在甲基芳烃与胺盐酸盐的氧化酰胺化反应中探讨了合成催化剂的催化活性。通过这种方法制备了各种伯，仲和叔酰胺。该催化剂的磁性使分离容易，并具有显着的催化剂可回收性。该催化剂可重复使用6次而其催化活性没有明显降低。
• Hypervalent iodine-catalyzed oxidative amidation of methylarenes
  作者：Kobra Azizi、Meghdad Karimi、Akbar Heydari

  DOI：10.1039/c4ra04215h

  日期：——

  iodine-catalyzed oxidative amidation of methylarenes to the corresponding amides by using an oxidant (tert-butyl hydroperoxide, 70% aqueous solution) is discussed. This oxidizing agent presented a high degree of selectivity for the oxidation of toluene to amide without oxidation to carboxylic acid. This reaction involves metal-free oxidation, a mild reaction condition and tert-butyl alcohol as the only

  讨论了通过使用氧化剂（叔丁基氢过氧化物，70％水溶液）将甲基芳烃高价碘催化的氧化酰胺化为相应的酰胺。该氧化剂对甲苯氧化为酰胺而不氧化为羧酸具有很高的选择性。该反应涉及无金属的氧化，温和的反应条件和叔丁醇作为唯一的副产物。
• Room-Temperature Debenzylation of <i>N</i>-Benzylcarboxamides by<i> N</i>-Bromosuccinimide
  作者：Ke Ding、Liping Kuang、Jing Zhou、Sheng Chen

  DOI：10.1055/s-2007-990795

  日期：2007.10

  A simple and highly efficient method has been developed with which to cleave the N-benzyl group on N-mono- or di­substituted carboxamides using N-bromosuccinimide (NBS) at room temperature. All the 31 substrates examined showed moderate to excellent deprotection yields. Our study also indicated that the debenzylation may involve an oxygen/light initiated free radical mechanism.

  开发了一种简单且高效的方法，可以在室温下使用N-溴琥珀酰亚胺（NBS）去除N-单取代或双取代羧酰胺上的N-苄基基团。所有31种被检验的底物表现出中等到优秀的去保护产率。我们的研究还表明，去苄基化可能涉及氧/光引发的自由基机制。