N-(4-hydroxy-3-methoxybenzyl)dodecanamide | 69693-11-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 酚类
• 英文名称: N-(4-hydroxy-3-methoxybenzyl)dodecanamide
• 英文别名: N-lauroylvanillylamine；N-vanillyl-dodecanamide；N-Vanillyl-dodecanamid；N-Vanillyl-laurinamid；N-(4-Oxy-3-methoxy-benzyl)-laurinsaeureamid；N-Lauryl-vanillylamin；Dodecanamide, N-((4-hydroxy-3-methoxyphenyl)methyl)-；N-[(4-hydroxy-3-methoxyphenyl)methyl]dodecanamide
• CAS: 69693-11-4
• 化学式: C₂₀H₃₃NO₃
• 分子量: 335.487
• InChiKey: QXOUXETZELPRMZ-UHFFFAOYSA-N

物化性质

• 熔点：
  67-67.5 °C
• 沸点：
  523.6±40.0 °C(Predicted)
• 密度：
  1.009±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.8
• 重原子数：
  24
• 可旋转键数：
  13
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.65
• 拓扑面积：
  58.6
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  月桂酰氯 、 香兰素胺盐酸盐 在 sodium hydroxide 作用下， 以 水 、 N,N-二甲基甲酰胺 、 四氢呋喃 为溶剂， 反应 19.0h， 以61.25%的产率得到N-(4-hydroxy-3-methoxybenzyl)dodecanamide
  参考文献：
  名称：

  Hansch模型在辣椒素和辣椒素中的应用：使用定量结构-活性关系的研究。辣椒素合成的新方法

  摘要：

  作为结构和活性之间定量关系研究的一部分，我们描述了两种类化合物的合成方法：辣椒素和辣椒素。总共合成了14个增加的侧链长度（从2到16个碳原子）的辣椒素。另外，已经合成了14个具有相同侧链的辣椒素以及衣壳和二氢衣壳，并且已经开发了用于合成这些化合物的新方法。产率为48.35至98.98％。已经发现，合成的辣椒素类和辣椒素类具有与天然化合物相似的亲脂性，并具有相似的生物学活性。与天然化合物相比，合成辣椒素和辣椒素的生物活性与亲脂性差异程度（较高或较低）成比例地降低。使用黄化的小麦测定生物活性（小麦胚芽鞘生物测定法，并通过将合成结果与其对应的天然化合物呈现的结果进行比较。发现的生物活性与合成化合物的亲脂性直接相关。

  DOI：

  10.1021/jf9035029

文献信息

• Vanilloids. 1. Analogs of capsaicin with antinociceptive and antiinflammatory activity
  作者：John M. Janusz、Brian L. Buckwalter、Patricia A. Young、Thomas R. LaHann、Ralph W. Farmer、Gerald B. Kasting、Maurice E. Loomans、Gary A. Kerckaert、Cherie S. Maddin

  DOI：10.1021/jm00070a002

  日期：1993.9

  As part of a program to establish structure-activity relationships for vanilloids, analogs of the pungent principle capsaicin, the alkyl chain portion of the parent structure (and related compounds derived from homovanillic acid) was varied. In antinociceptive and antiinflammatory assays (rat and mouse hot plate and croton oil-inflamed mouse ear), compounds with widely varying alkyl chain structures

  作为建立香草醛的结构活性关系的程序的一部分，辛辣成分辣椒素的类似物，母体结构的烷基链部分（以及衍生自高香草酸的相关化合物）发生了变化。在抗伤害感受和抗炎试验（大鼠和小鼠热板以及巴豆油刺激的小鼠耳朵）中，具有广泛变化的烷基链结构的化合物具有活性。短链化合物在上述测定中通过全身给药具有活性，但它们保留了辣椒素的高刺激性和急性毒性特征。相比之下，长链顺式不饱和物NE-19550（香草基油酰胺）和NE-28345（油基单香草酰胺）具有口服活性，刺激性较低，并且比辣椒素的急性毒性小。
• Enzymatic synthesis of capsaicin analogs with liver acetone powder
  作者：Kenji Kobata、Koichi Yoshikawa、Masahiro Kohashi、Tatsuo Watanabe

  DOI：10.1016/0040-4039(96)00429-7

  日期：1996.4

  The enzymatic synthesis of capsaicin analogs with saturated or unsaturated acyl moieties has been achieved by using liver acetone powder as a catalyst.

  通过使用肝丙酮粉末作为催化剂已经实现了具有饱和或不饱和酰基部分的辣椒素类似物的酶促合成。
• A Novel Acylase from <i>Streptomyces mobaraensis</i> that Efficiently Catalyzes Hydrolysis/Synthesis of Capsaicins as Well as <i>N</i>-Acyl-<scp>l</scp>-amino Acids and <i>N</i>-Acyl-peptides
  作者：Mayuko Koreishi、Demin Zhang、Hiroyuki Imanaka、Koreyoshi Imamura、Shuji Adachi、Ryuichi Matsuno、Kazuhiro Nakanishi

  DOI：10.1021/jf052102k

  日期：2006.1.1

  A novel enzyme that catalyzes efficient hydrolysis of capsaicin (8-methyl-N-vanillyl-6-nonenamide) was isolated from the culture broth of Streptomyces mobaraensis. The enzyme consisted of two dissimilar subunits with molecular masses of 61 and 19 kDa. The enzyme was activated and stabilized in the presence of Co2+. It showed a pH optimum of about 8 and was stable at temperatures of up to 55 degrees C for 1 h at pH 7.8. The specific activity of the enzyme for the hydrolysis of capsaicin was 10(2)-10(4) times higher than those for the enzymes reported to date. In an aqueous/n-hexane biphasic system, capsaicin analogues such as octanoyl, decanoyl, and lauroyl vanillylamides were synthesized from the corresponding fatty acids and vanillylamine at yields of 50% or greater. In addition, the enzyme catalyzed the deacylation of N-lauroyl-L-amino acids and N-lauroyl-L-dipeptides and the efficient synthesis of N alpha-lauroyl-L-lysine, N epsilon-lauroyl-L-lysine, and various N-lauroyl-peptides in aqueous solution in both the absence and the presence of glycerol.
• Ford-Moore; Phillips, Recueil des Travaux Chimiques des Pays-Bas, 1934, vol. 53, p. 855
  作者：Ford-Moore、Phillips

  DOI：——

  日期：——
• Highly efficient synthesis of capsaicin analogues by condensation of vanillylamine and acyl chlorides in a biphase H2O/CHCl3 system
  作者：Bo Wang、Fan Yang、Yi-Fan Shan、Wen-Wei Qiu、Jie Tang

  DOI：10.1016/j.tet.2009.04.046

  日期：2009.7

  Highly efficient synthesis of capsaicin analogues was developed using condensation of vanillylamine with acyl chlorides in a biphase H2O/CHCl3 System under mild conditions. For C-4-C-18 aliphatic or aromatic acyl chlorides, the yields were up to 93-96% with high purity after a simple work-up procedure, and only 1-1.16 equiv of acyl chloride was needed in the reaction. (C) 2009 Elsevier Ltd. All rights reserved.