N-propylcinnamamide | 6329-15-3

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 肉桂酸及其衍生物
• 英文名称: N-propylcinnamamide
• 英文别名: Zimtsaeure-n-propylamid；n-Propyl cinnamic amide；3-phenyl-N-propylprop-2-enamide
• CAS: 6329-15-3
• 化学式: C₁₂H₁₅NO
• 分子量: 189.257
• InChiKey: BHKSMXCCTNJRDN-UHFFFAOYSA-N

物化性质

• 沸点：
  324.52°C (rough estimate)
• 密度：
  1.0356 (rough estimate)

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  14
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  29.1
• 氢给体数：
  1
• 氢受体数：
  1

安全信息

• 海关编码：
  2924299090

反应信息

• 作为反应物：
  描述：

  N-propylcinnamamide 在 氢气 作用下， 以 甲醇 为溶剂， 反应 5.0h， 以98%的产率得到3-phenyl-N-propylpropanamide
  参考文献：
  名称：

  硅藻土-聚苯胺负载的钯催化剂用于化学选择性加氢反应

  摘要：

  涂覆在硅藻土颗粒上的聚苯胺被用作负载钯催化剂的载体。这种杂化的Celite•PANI•Pd系统被用作化学选择性氢化反应的有效催化剂。该催化剂通过常用的光谱，分析技术进行表征，并针对环境条件下的氢化反应进行了研究。温和的反应条件可以控制反应，并在转化数上实现出色的选择性。碳-碳双键的氢化作用优于其他极性π-键系统，而不稳定的官能团（如苄基醚，苄基酯，氰基，硝基和卤素）不受影响。伯胺被转化为N，N‐二甲基胺与甲醛，香豆素的双键被选择性地氢化而不打开内酯官能团。

  DOI：

  10.1002/aoc.4767
• 作为产物：
  描述：

  N-((1,2-dimethyl-1H-indol-3-yl)methyl)-N-propylcinnamamide 在 三氟甲烷磺酸甲酯 作用下， 以 乙醇 、 水 为溶剂， 反应 12.0h， 以90%的产率得到N-propylcinnamamide
  参考文献：
  名称：

  Methyl-triflate-mediated dearylmethylation of N-(arylmethyl)carboxamides via the retro-Mannich reaction induced by electrophilic dearomatization/rearomatization in an aqueous medium at room temperature

  摘要：

  在无金属条件下，在水介质中通过亲电脱芳香化/重芳香化实现了N-(芳甲基)羧酰胺的去芳甲基化。

  DOI：

  10.1039/c9gc00176j

文献信息

• Stereodivergent Synthesis through Catalytic Asymmetric Reversed Hydroboration
  作者：Tao-Tao Gao、Wen-Wen Zhang、Xin Sun、Hou-Xiang Lu、Bi-Jie Li

  DOI：10.1021/jacs.8b13520

  日期：2019.3.20

  The control of chemo-, regio-, diastereo-, and enantioselectivity is a central theme in organic synthesis. The capability to obtain the full set of stereoisomers of a molecule would significantly enhance the efficiency for the synthesis of natural product analogues and creation of chiral compound libraries for drug discovery. Despite the tremendous progress achieved in the field of asymmetric synthesis

  化学选择性、区域选择性、非对映选择性和对映选择性的控制是有机合成的中心主题。获得分子的全套立体异构体的能力将显着提高合成天然产物类似物和创建用于药物发现的手性化合物库的效率。尽管过去几十年在不对称合成领域取得了巨大进步，但在催化剂控制的反应中精确控制相对和绝对构型，从而产生多个立体中心仍然是一个重大的合成挑战。我们在这里报告了具有迄今为止无法实现的选择性的催化剂控制的硼氢化反应的发展。Rh 催化的 α, β-不饱和羰基化合物与频哪醇硼烷的硼氢化反应以高水平的区域-、非对映-、和对映选择性提供具有两个邻位立体中心的硼氢化产物。Through the appropriate choice of substrate geometry ( E or Z) and ligand enantiomer ( S or R), all the possible diastereoisomers are readily
• Enhancing Ligand‐Free Fe‐Catalyzed Aminocarbonylation of Alkynes by ZrF ₄
  作者：Zijun Huang、Yanan Dong、Yudong Li、Mohamed Makha、Yuehui Li

  DOI：10.1002/cctc.201900995

  日期：2019.11.7

  Zirconium fluoride was utilized to promote efficiently iron‐catalyzed aminocarbonylation between alkynes and amines without the use of extra ligands. In particular, this new system is applicable to a wide range of amine and alkyne substrates affording α,β‐unsaturated amides in good to excellent yields. Preliminary mechanistic studies reveal the activation model involving interactions of ZF4 with both

  氟化锆可用于有效促进炔烃和胺之间铁催化的氨基羰基化反应，而无需使用额外的配体。尤其是，该新系统可适用于各种胺和炔烃底物，从而以良好或优异的收率提供α，β-不饱和酰胺。初步的机理研究表明，活化模型涉及ZF 4与铁催化剂和胺底物的相互作用。
• Natural α-methylenelactam analogues: Design, synthesis and evaluation of α-alkenyl-γ and δ-lactams as potential antifungal agents against Colletotrichum orbiculare
  作者：Wang Delong、Wang Lanying、Wu Yongling、Song Shuang、Feng Juntao、Zhang Xing

  DOI：10.1016/j.ejmech.2017.02.050

  日期：2017.4

  In our continued efforts to improve the potential utility of the alpha-methylene-gamma-lactone scaffold, 62 new and 59 known natural alpha-methylenelactam analogues including alpha-methylene-gamma- lactams, alpha-arylidene- gamma and delta-lactams, and 3-arylideneindolin-2-ones were synthesized as the bioisosteric analogues of the amethylenelactone scaffold. The results of antifungal and cytotoxic activity indicated that among these derivatives compound (E)-1-(2, 6-dichlorobenzyl)-3-(2-fluorobenzylidene) pyrrolidin-2-one (Py51) possessed good selectivity with the highest antifungal activity against Colletotrichum orbiculare with IC50 - 10.4 mu M but less cytotoxic activity with IC50 - 141.2 mu M (against HepG2 cell line) and 161.2 mu M ( against human hepatic L02 cell line). Ultrastructural change studies performed by transmission electron microscope showed that Py51 could cause important cell morphological changes in C. orbiculare, such as plasma membrane detached from cell wall, cell wall thickening, mitochondria disruption, a dramatic increase in vacuolation, and eventually a complete loss in the integrity of organelles. Significantly, mitochondria appeared one of the primary targets, as confirmed by their remarkably aberrant morphological changes. Analysis of structureeactivity relationships revealed that incorporation of the aryl group into the alpha-exo methylene and the N-benzyl substitution increased the activity. Meanwhile, the alpha-arylidene-gamma-lactams have superiority in selectivity over the 3-arylideneindolin-2-ones. Based on the results, the N- benzyl substituted a-(2-fluorophenyl)-gamma-lactam was identified as the most promising natural- based scaffold for further discovering and developing improved crop- protection agents. (c) 2017 Elsevier Masson SAS. All rights reserved.
• Lipase-Catalyzed Solvent-Free Amidation of Phenolic Acids
  作者：Parshant Kaushik、Najam Akhtar Shakil、Jitendra Kumar、Braj Bhushan Singh

  DOI：10.1080/00397911.2014.974611

  日期：2015.3.4

  A series of N-alkyl-substituted amides, based on various phenolic acids, have been synthesized by the condensation of equimolar amounts of phenolic acids with different alkyl amines in the presence of Candida antarctica lipase at 60-90 degrees C in 16-20 h. The reactions were carried out in a solvent-free system without the use of any activating agents. All the products were obtained in appreciable amounts and the yields for different compounds varied between 75.6% and 83.5%. The synthesized compounds were characterized using spectroscopy techniques, namely infrared and NMR (H-1 and C-13).