(E)-N-(2-羟基乙基)-3-(3,4,5-三甲氧基苯基)丙-2-烯酰胺 | 30687-11-7

• 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
• 中文名称: (E)-N-(2-羟基乙基)-3-(3,4,5-三甲氧基苯基)丙-2-烯酰胺
• 英文名称: (E)-N-2-hydroxyethyl 3,4,5-trimethoxycinnamamide
• 英文别名: N-(2-hydroxyethyl)-3-(3,4,5-trimethoxyphenyl)-2-propenamide；(E)-N-(2-hydroxyethyl)-3-(3,4,5-trimethoxyphenyl)acrylamide；N-(2-Hydroxyethyl)-3,4,5-trimethoxycinnamamide；(E)-N-(2-hydroxyethyl)-3-(3,4,5-trimethoxyphenyl)prop-2-enamide
• CAS: 30687-11-7
• 化学式: C₁₄H₁₉NO₅
• 分子量: 281.309
• InChiKey: ASJISPPWLSJQIS-SNAWJCMRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.9
• 重原子数：
  20
• 可旋转键数：
  7
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  77
• 氢给体数：
  2
• 氢受体数：
  5

安全信息

• 海关编码：
  2924299090

反应信息

• 作为产物：
  描述：

  (E)-3-(3,4,5-trimethoxyphenyl)acryloyl chloride 以 甲苯 为溶剂， 反应 16.5h， 生成 (E)-N-(2-羟基乙基)-3-(3,4,5-三甲氧基苯基)丙-2-烯酰胺
  参考文献：
  名称：

  N-酰基-2-哌啶酮的轻度，无金属和无保护的氨基转移为氨基酸，氨基醇和脂肪胺以及N-酰基-2-哌啶酮的酯化

  摘要：

  一种高选择性，温和且无金属的方案，可在短反应时间（30–45分钟）内将N-酰基哌啶酮转氨成未保护的氨基酸，氨基醇和其他脂肪族胺，且无其他碱且在纯净条件下进行。N酰基哌啶酮在85°C下用脂肪族醇酯化。酰胺键捻，τ= -20.39°和pyramidalization，χ Ñ = -11.73°。

  DOI：

  10.1002/ejoc.201900517

文献信息

• A simple synthesis of trans-3,4,5-trimethoxycinnamamides and evaluation of their biologic activity
  作者：Jae-Chul Jung、Dongguk Min、Heena Lim、Sohyeon Moon、Mankil Jung、Seikwan Oh

  DOI：10.1007/s00044-012-0415-1

  日期：2013.10

  A simple synthesis and biologic evaluation of trans-3,4,5-trimethoxycinnamamides 10a–e and 11 as novel antinarcotic agents is described. The synthetic key strategies involve condensation reaction and coupling reaction to generate trans-3,4,5-trimethoxycinnamamides 10a–e and 11. They were evaluated for free radical scavenging, inhibitory action for neurotoxicity in cultured neurons, and antinarcotic

  一个简单的合成和生物评价反式-3,4,5-三甲氧基肉桂酰胺10a-e和11作为新型抗麻醉药。合成关键策略涉及缩合反应和偶联反应，以生成反式-3,4,5-三甲氧基肉桂酰胺10a–e和11。对它们的自由基清除，培养的神经元对神经毒性的抑制作用以及小鼠的抗麻醉活性进行了评估。研究发现，化合物10a，10d和10e对谷氨酸诱导的神经毒性具有明显的抑制作用，而10a–e和11则具有抑制作用。 在小鼠中显示出高的抗麻醉活性。
• Synthesis and antidepressant-like action of N-(2-hydroxyethyl) cinnamamide derivatives in mice
  作者：Xian-Qing Deng、Di Wu、Cheng-Xi Wei、Zhe-Shan Quan

  DOI：10.1007/s00044-010-9470-7

  日期：2011.11

  This study described the chemical synthesis and pharmacological evaluation of a series of N-(2-hydroxyethyl) cinnamamide derivatives. The structures of them were characterized by IR, (1)H-NMR, MS and elemental analysis. Their antidepressant activities were evaluated by the forced swimming test (FST) and tail suspension test (TST). Pharmacological results of these compounds showed that some of them, given orally, significantly reduced the immobility time in the FST and TST, indicating the antidepressant-like action. Among them, compounds N-(2-hydroxyethyl)cinnamamide (1g), (E)-3-(4-hydroxy-3-methoxyphenyl)-N-(2-hydroxyethyl)acrylamide (1i) and (E)-N-(2-hydroxyethyl)-3-(3-hydroxyphenyl)acrylamide (1n), active in the two models, were considered as the most promising compounds in this study.
• Mild, Metal-Free and Protection-Free Transamidation of N-Acyl-2-piperidones to Amino Acids, Amino Alcohols and Aliphatic Amines and Esterification of N-Acyl-2-piperidones
  作者：Muthuraman Subramani、Saravana Kumar Rajendran

  DOI：10.1002/ejoc.201900517

  日期：2019.6.16

  selective mild and metal‐free protocol for transamidation of N‐acyl piperidones to unprotected amino acids, amino alcohols and other aliphatic amines at short reaction times (30–45 min), with no additional base and at neat condition. Esterification of N‐acyl piperidones with aliphatic alcohols at 85 °C. Amide bond twist, τ = –20.39° and pyramidalization, χN = –11.73°.

  一种高选择性，温和且无金属的方案，可在短反应时间（30–45分钟）内将N-酰基哌啶酮转氨成未保护的氨基酸，氨基醇和其他脂肪族胺，且无其他碱且在纯净条件下进行。N酰基哌啶酮在85°C下用脂肪族醇酯化。酰胺键捻，τ= -20.39°和pyramidalization，χ Ñ = -11.73°。