ethyl dodecanoyl carbonate | 21260-90-2

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 有机碳酸及其衍生物
• 英文名称: ethyl dodecanoyl carbonate
• 英文别名: Ethoxycarbonyl dodecanoate；ethoxycarbonyl dodecanoate
• CAS: 21260-90-2
• 化学式: C₁₅H₂₈O₄
• 分子量: 272.385
• InChiKey: MYZBNECHXQEZNC-UHFFFAOYSA-N

物化性质

• 沸点：
  337.7±25.0 °C(Predicted)
• 密度：
  0.962±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.8
• 重原子数：
  19
• 可旋转键数：
  14
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.87
• 拓扑面积：
  52.6
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  ethyl dodecanoyl carbonate 在 palladium on activated charcoal 盐酸 、 氢气 作用下， 以 四氢呋喃 、 甲醇 、 乙醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 38.0h， 生成 N-(2-deoxy-2-glycylamino-β-D-glucopyranosyl)-N-dodecyldodecanamide
  参考文献：
  名称：

  Syntheses of Peptidoglycolipid Analogs with Distinct Immunomodulating Activities

  摘要：

  Amphiphilic 2-amino-2-deoxy-beta-D-glucopyranosylamides were synthesized from N-protected glucosamine derivatives via N-glycosidation with fatty amines, subsequent N-acylation with fatty acid derivatives and deprotection. They could further be modified with amino acids to give peptido-glycopyranosyl amides, some of which exhibited strong immunostimulatory (BAY Q8939, 8) or immunoadjuvant (BAY R1005, 9) activities.

  DOI：

  10.1080/07328300008544102
• 作为产物：
  描述：

  月桂酸 、 氯甲酸乙酯 在 三乙胺 作用下， 以 乙腈 为溶剂， 反应 0.5h， 生成 ethyl dodecanoyl carbonate
  参考文献：
  名称：

  在水性有机溶剂中通过混合的碳羧酸酐方便地合成包含α-氨基酸和脂肪酸的对乙酰氨基酚类似物

  摘要：

  使用苯胺衍生物在MeCN水溶液中，可以轻松地以相应的α-氨基酸和脂肪酸混合碳酸酐从77-99％的产率合成含α-氨基酸和脂肪酸的对乙酰氨基酚类似物。

  DOI：

  10.1016/j.tetlet.2013.08.028

文献信息

• Synthesis of Acetaminophen Analogues Containing α-Amino Acids and Fatty Acids for Inhibiting Hepatotoxicity
  作者：Seunghee Jung、Yuya Kawashima、Takuya Noguchi、Nobuyuki Imai

  DOI：10.1055/s-0037-1611893

  日期：2019.10

  reactive metabolite N-acetyl-p-benzoquinone imine (NAPQI). We have obtained acetaminophen analogues in 57–99% yields by using aniline derivatives with protected α-amino acids and fatty acids via the corresponding mixed carbonic carboxylic anhydrides in aqueous MeCN. We have also succeeded in synthesizing AM404 analogues in 76–97% yields, which are expected to be promising candidates for reducing hepatotoxicity

  献给EJ科里教授在他的90之际个生日。 抽象的 对乙酰氨基酚是一种流行的解热镇痛药，与非甾体类抗炎药（NSAIDs）相比，抗炎作用弱，副作用发生率低。然而，对乙酰氨基酚由于反应性代谢产物N-乙酰基-对苯醌亚胺（NAPQI）而引起肝毒性。通过在水性MeCN中通过相应的混合碳羧酸酐使用受保护的α-氨基酸和脂肪酸的苯胺衍生物，我们以57-99％的产率获得了对乙酰氨基酚类似物。我们还成功地以76–97％的产率合成了AM404类似物，有望降低肝毒性。 对乙酰氨基酚是一种流行的解热镇痛药，与非甾体类抗炎药（NSAIDs）相比，抗炎作用弱，副作用发生率低。然而，对乙酰氨基酚由于反应性代谢产物N-乙酰基-对苯醌亚胺（NAPQI）而引起肝毒性。通过在水性MeCN中通过相应的混合碳羧酸酐使用受保护的α-氨基酸和脂肪酸的苯胺衍生物，我们以57-99％的产率获得了对乙酰氨基酚类似物。我们还成功地以76–97％的产
• Syntheses of glycosylamides as glycolipid analogs
  作者：Oswald Lockhoff、Peter Stadler

  DOI：10.1016/s0008-6215(98)00278-x

  日期：1998.12

  In search of a simple synthetic access to analogs of naturally occurring glycolipids, glycosylamides have been synthesised in a two-step procedure from unprotected sugars, long-chain amines, and fatty acids. The N-glycosylation proceeded stereospecifically yielding crystalline beta-glycopyranosylamines. C-13 NMR spectroscopy of the glycosylamines in organic solvents revealed partial anomerisation, leading to alpha-glycosylamines and in part to corresponding N-furanosides. Selective N-acylation of either pure beta-glycosylamines or anomeric mixtures thereof with activated fatty acid led to formation of beta-glycosylamides exclusively. As evidenced by NMR spectroscopy, the glycosylamides exhibited rotameric isomerism. The glycosylamides were found to be strong stimulators of the specific immune response against antigens. (C) 1998 Elsevier Science Ltd. All rights reserved.
• Design, synthesis and antibacterial activity of novel andrographolide derivatives
  作者：Zhongli Wang、Pei Yu、Gaoxiao Zhang、Lipeng Xu、Dingyuan Wang、Liang Wang、Xiangping Zeng、Yuqiang Wang

  DOI：10.1016/j.bmc.2010.04.094

  日期：2010.6.15

  A series of andrographolide derivatives were synthesized through a facile condensation reaction with different carboxylic acids. The new compounds were characterized and screened for their antibacterial activities. A number of the new compounds significantly reduced bacterial quorum sensing virulence factors production in Pseudomonas aeruginosa, essential for pathogenesis. Compound 11b showed the best activity among all the new compounds. (C) 2010 Elsevier Ltd. All rights reserved.
• COMPOUNDS FOR A CONTROLLED RELEASE OF ACTIVE COMPOUNDS
  申请人：FIRMENICH SA

  公开号：EP1373368A1

  公开（公告）日：2004-01-02
• [EN] COMPOUNDS FOR A CONTROLLED RELEASE OF ACTIVE COMPOUNDS<br/>[FR] COMPOSES SERVANT A EFFECTUER LA LIBERATION CONTROLEE DE COMPOSES ACTIFS
  申请人：FIRMENICH & CIE

  公开号：WO2002077074A1

  公开（公告）日：2002-10-03

  The present invention relates to the field of perfumery. More particularly, it concerns a compound having supported carbamoyl/ester moieties which comprise an ester capable of liberating an active compound and, in proximity, a carbamoyl function facilitating the release of the said active compound. The present application concerns also the uses of said compound, as well as the compositions comprising said compounds.