N-(4-(tert-butyl)benzyl)benzamide | 1334676-88-8

• 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: N-(4-(tert-butyl)benzyl)benzamide
• 英文别名: N-[(4-tert-butylphenyl)methyl]benzamide
• CAS: 1334676-88-8
• 化学式: C₁₈H₂₁NO
• 分子量: 267.371
• InChiKey: JGVXJAHDUMIINM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  20
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.28
• 拓扑面积：
  29.1
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  N-(4-(tert-butyl)benzyl)benzamide 在 tropylium tetrafluoroborate 、 频那醇硼烷 、 sodium hydroxide 、 盐酸 作用下， 以 乙醚 为溶剂， 反应 3.0h， 以66%的产率得到N-benzyl-1-(4-(tert-butyl)phenyl)methanaminium chloride
  参考文献：
  名称：

  Tropyium 四氟硼酸盐促进腈、亚胺和酰胺的硼氢化

  摘要：

  腈类（现成的合成前体）转化为胺、亚胺或酰胺是合成实验室和工业化学中重要的化学转化。有各种各样的方法来促进这种类型的化学。但是，仍然存在一些限制。为了追求实用且环境友好的腈硼氢化反应，我们开发了一种新的有机催化方法，用频哪醇硼烷将腈、亚胺或酰胺还原为胺。通过将进一步的官能化反应引入到一锅中的粗硼氢化混合物中，可以方便地获得来自这些胺的有价值的衍生物。

  DOI：

  10.1039/d2gc01905a
• 作为产物：
  描述：

  对硝基苯甲酸 在 氯化亚砜 、 palladium 10% on activated carbon 、 氢气 、 三乙胺 作用下， 以 二氯甲烷 、 乙酸乙酯 为溶剂， 反应 3.0h， 生成 N-(4-(tert-butyl)benzyl)benzamide
  参考文献：
  名称：

  Design, Synthesis, and Insecticidal Evaluation of New Benzoylureas Containing Amide and Sulfonate Groups Based on the Sulfonylurea Receptor Protein Binding Site for Diflubenzuron and Glibenclamide

  摘要：

  On the basis of the sulfonylurea receptor (SUR) protein binding site for diflubenzuron and glibenclamide, 15 new benzoylphenylureas containing amide and sulfonate groups were designed and synthesized. Their structures were characterized by H-1 nuclear magnetic resonance (NMR) and elemental analysis [or high-resolution mass spectrometry (HRMS)]. The larvicidal activities of the new compounds against oriental armyworm and diamondback moth were evaluated. Compound II-3 showed nearly the same level of insecticidal activity against oriental armyworm as commercial insecticide flucycloxuron and, thus, emerged as a new lead compound for the development of new benzoylurea insecticides.

  DOI：

  10.1021/jf304468b

文献信息

• Graphene Oxide: A Metal‐Free Carbocatalyst for the Synthesis of Diverse Amides under Solvent‐Free Conditions
  作者：Khushbu P. Patel、Eknath M. Gayakwad、Vilas V. Patil、Ganapati S. Shankarling

  DOI：10.1002/adsc.201801673

  日期：2019.4.23

  solvent‐free reaction conditions providing desired products in good to excellent yields. The one‐pot synthesis of 2,3‐Dihydro‐5H‐benzo[b]‐1,4‐thiazepin‐4‐one moiety by GO catalyzed Aza Michael addition followed by intramolecular transamidation is also described. A plausible reaction mechanistic pathway involving H‐bonding is discussed. The graphene oxide can be recycled and reused up to five cycles without

  证明了环保，廉价，碳催化剂，氧化石墨烯（GO）促进了各种羧酰胺与脂肪族，环状和芳香族胺的高效无金属氨基转移。该协议同样适用于邻苯二甲酰亚胺，尿素和硫代酰胺，以确定其适应性。存在于氧化石墨烯表面的羰基（-C = O），环氧（-O-），羧基（-COOH）和羟基（-OH）等氧化官能团赋予催化剂酸性。氧化石墨烯本质上是多相的，可以在无溶剂的反应条件下有效地工作，从而以高至优异的收率提供所需的产物。还描述了GO催化的Aza Michael加成反应，然后进行分子内氨基转移，一锅法合成2,3-二氢-5H-苯并[b] -1,4-噻吩并-4-酮部分。讨论了涉及氢键的可能的反应机理途径。氧化石墨烯可以循环使用多达五个周期，而催化活性却没有太大损失。
• UV-Light-Induced N-Acylation of Amines with α-Diketones
  作者：Zhihui Xu、Tianbao Yang、Niu Tang、Yifeng Ou、Shuang-Feng Yin、Nobuaki Kambe、Renhua Qiu

  DOI：10.1021/acs.orglett.1c01599

  日期：2021.7.16

  induced by ultraviolet (UV) light. Forty-six examples with various functional groups are explored at room temperature with irradiation by three 26 W UV lamps (350–380 nm). The yield reaches 97%. The gram scale experiment product yield is 76%. Moreover, this system can be applied to the synthesis of several amino acid derivatives. Mechanistic studies show that benzoin is generated in situ from benzil under

  在此，我们开发了一种温和的方法，用于由紫外线 (UV) 光诱导的 α-二酮对伯胺和仲胺的N-酰化。在室温下用三个 26 W 紫外线灯 (350–380 nm) 照射探索了 46 个具有不同官能团的例子。收率达到97%。克级实验产物收率为76%。此外，该系统可应用于多种氨基酸衍生物的合成。机理研究表明，安息香是在紫外线照射下由苯偶姻原位生成的。
• Silica boron–sulfuric acid nanoparticles (SBSANs): preparation, characterization and their catalytic application in the Ritter reaction for the synthesis of amide derivatives
  作者：Ali Khalafi-Nezhad、Habib ollah Foroughi、Mohammad Mahdi Doroodmand、Farhad Panahi

  DOI：10.1039/c1jm11154j

  日期：——

  Among a number of different heterogeneous and homogeneous catalysts, silica boron–sulfuric acid nanoparticles (SBSANs) with both protic and Lewis acidic sites were shown to be the most active and recyclable catalyst in the Ritter reaction. Various amide derivatives were synthesized from alcohols and nitrilesvia a one-step and easy process in the presence of a catalytic amount of SBSAN at room temperature in solvent free conditions with excellent isolated yields. The silica boron–acid nanoparticles (SBANs) were regularly synthesized during the modification of the silica support by boric acid [B(OH)3] during the chemical vapor deposition (CVD) process and subsequently, this material was reacted with chlorosulfonic acid (ClSO3H) to obtain the SBSAN catalyst. The new catalyst was characterized using some different microscopic and spectroscopic techniques such as patterned X-ray diffraction (XRD), transmission electron microscopy (TEM), scanning electron microscopy (SEM), FT-Raman spectrometry and FT-IR spectroscopy. Thermal behavior of the SBSAN catalyst was also investigated by a thermogravimetric (TG) analyzer.

  在一系列不同的均相和非均相催化剂中，硅硼硫酸纳米粒子（SBSANs）由于同时具有质子酸和路易斯酸性位点，被证明是Ritter反应中最活跃且可循环使用的催化剂。通过一种简单的一步法过程，在无溶剂条件下，使用催化量的SBSANs并在室温下，从醇和腈合成了多种酰胺衍生物，分离产率极佳。硅硼酸纳米粒子（SBANs）是在化学气相沉积（CVD）过程中通过硼酸[B(OH)3]改性硅载体时定期合成的，随后，这种材料与氯磺酸（ClSO3H）反应以获得SBSAN催化剂。新催化剂通过一些不同的微观和光谱技术进行表征，如X射线衍射（XRD）、透射电子显微镜（TEM）、扫描电子显微镜（SEM）、傅里叶变换拉曼光谱和傅里叶变换红外光谱。SBSAN催化剂的热行为也通过热重（TG）分析仪进行了研究。
• Graphene oxide: a convenient metal-free carbocatalyst for facilitating amidation of esters with amines
  作者：Khushbu P. Patel、Eknath M. Gayakwad、Ganapati S. Shankarling

  DOI：10.1039/c9nj05283f

  日期：——

  Herein, we report a graphene oxide (GO) catalyzed condensation of non-activated esters and amines, that can enable diverse amides to be synthesized from abundant ethyl esters forming only volatile alcohol as a by-product. GO accelerates ester to amide conversion in the absence of any additives, unlike other catalysts. A wide range of ester and amine substrates are screened to yield the respective amides

  在这里，我们报告了未活化的酯和胺的氧化石墨烯（GO）催化的缩合反应，可以使丰富的乙酯合成多种酰胺，而仅形成挥发性醇作为副产物。与其他催化剂不同，在没有任何添加剂的情况下，GO可以加速酯到酰胺的转化。筛选各种酯和胺底物，以良好至优异的产率产生各自的酰胺。改善的催化活性可以归因于存在于氧化石墨烯表面上的氧化官能团，其与反应物形成H键，从而加速反应。改进的收率和广泛的官能团耐受性是已开发方案的一些重要功能。
• Base-promoted amide synthesis from aliphatic amines and ynones as acylation agents through C–C bond cleavage
  作者：Guolin Cheng、Weiwei Lv、Changsheng Kuai、Si Wen、Shangyun Xiao

  DOI：10.1039/c7cc09310a

  日期：——

  A new protocol for the synthesis of amides via base-promoted cleavage of the C(sp)–C(CO) bond of ynones with aliphatic primary and secondary amines under transition-metal-, ligand-, and oxidant-free conditions has been developed. This method exhibits a wide substrate scope, high functional group tolerance and exclusive chemoselectivity, as well as mild reaction conditions.

  在无过渡金属，无配体和无氧化剂的条件下，开发了一种通过碱促进炔酮与脂肪族伯胺和仲胺的C（sp）–C（CO）键的碱促裂解来合成酰胺的新方案。该方法具有较宽的底物范围，较高的官能团耐受性和独有的化学选择性以及温和的反应条件。