(异丁基碳酸)硬脂酸酐 | 592517-85-6

• 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
• 中文名称: (异丁基碳酸)硬脂酸酐
• 英文名称: 2-Methylpropoxycarbonyl octadecanoate
• CAS: 592517-85-6
• 化学式: C₂₃H₄₄O₄
• 分子量: 384.6
• InChiKey: HWQUJRVCYRIMPW-UHFFFAOYSA-N

物化性质

• 沸点：
  450.5±28.0 °C(Predicted)
• 密度：
  0.925±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  10
• 重原子数：
  27
• 可旋转键数：
  21
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.91
• 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：

  (异丁基碳酸)硬脂酸酐 在 吡啶 、 三苯基膦 作用下， 以 二氯甲烷 、 邻二甲苯 为溶剂， 反应 24.0h， 生成 2-amino-6-benzyloxy-8-stearylpurine
  参考文献：
  名称：

  一种改进的制备 8-取代鸟嘌呤的程序可用电子补充信息 (ESI)：新化合物的表征。见http://www.rsc.org/suppdata/cc/b3/b302529b/

  摘要：

  描述了使用新的磷 (III) 介导的 4-acylamino-5-nitrosopyrimidines 环化作为关键步骤制备 8-取代鸟嘌呤。

  DOI：

  10.1039/b302529b
• 作为产物：
  描述：

  硬脂酸 、 氯甲酸异丁酯 在 N-甲基吗啉 作用下， 以 四氢呋喃 为溶剂， 生成 (异丁基碳酸)硬脂酸酐
  参考文献：
  名称：

  以2-甲基-1,4-萘醌为底物的衍生物和维生素K依赖性羧化酶的抑制剂。

  摘要：

  已经制备了一系列含有N-末端2-甲基-1，4-萘醌基团的肽或具有这种结构的类似物作为大鼠肝脏微粒体维生素K依赖性羧化酶的潜在底物或抑制剂。母体化合物gamma-2-（甲基-1,4-萘醌基-3）丁酰基-Glu-Glu-Leu-OMe是低浓度羧化酶的良好底物，Km约为50 microM。这比已经合成的大多数简单肽底物的Km低大约2个数量级。用其去甲基类似物，萘基或硬脂基取代2-甲基-1,4-萘醌基会降低底物的有效性。在较高浓度下，母体化合物及其去甲基类似物是维生素K依赖性羧化反应的有效抑制剂。

  DOI：

  10.1021/jm00375a020

文献信息

• Inhibition of in Vitro Prostaglandin and Leukotriene Biosyntheses by Cinnamoyl-.BETA.-phenethylamine and N-Acyldopamine Derivatives.
  作者：Chen-Fang TSENG、Satoshi IWAKAMI、Akihiro MIKAJIRI、Masaaki SHIBUYA、Fumio HANAOKA、Yutaka EBIZUKA、Kosashi PADMAWINATA、Ushio SANKAWA

  DOI：10.1248/cpb.40.396

  日期：——

  N-trans- and N-cis-Feruloyltyramines were isolated as the inhibitors of in vitro prostaglandin (PG) synthesis from an Indonesian medicinal plant, Ipomoea aquatica (Convolvulaceae). In order to clarify structure activity relationships, cinnamoyl-β-phenethylamines with possible combinations of naturally occurring cinnamic acids and β-phenethylamines were synthesized and tested for their inhibitory activities against PG synthetase and arachidonate 5-lipoxygenase. The compounds containing catechol groups such as N-caffeoyl-β-phenethylamine (CaP) showed higher inhibitory effects on PG synthetase. The catechol group was found to be essential for the inhibition of arachidonate 5-lipoxygenase. The investigation of concentration dependent effects on PG biosynthesis revealed that CaP enhanced PG biosynthesis at a lower concentration range, whereas it inhibited the reaction at a higher concentration. The effects of CaP on each reaction step were investigated with purified PG endoperoxide synthase and microsomal PG synthetase. CaP inhibited the cyclooxygenase reaction, while it enhanced the hydroperoxidase reaction. N-Acyldopamines which contain catechol and lipophylic group were synthesized from dopamine and fatty acids to test their inhibitory effects on arachidonate 5-lipoxygenase. N-Linoleoyldopamine was the most active compound and its IC50 value was 2.3nM in our assay system, in which an IC50 value of AA 861, a specific inhibitor of 5-lipoxygenase, was 8nM.

  N-反式和N-顺式-阿魏酰基酪胺是从印尼药用植物空心菜（旋花科）中分离得到的体外前列腺素（PG）合成抑制剂。为了阐明结构活性关系，合成了可能由天然存在的肉桂酸和β-苯乙胺组合得到的肉桂酰-β-苯乙胺，并测试了它们对PG合成酶和花生四烯酸5-脂氧合酶的抑制活性。含有儿茶酚基团的化合物，如N-咖啡酰基-β-苯乙胺（CaP），显示出对PG合成酶更高的抑制效果。儿茶酚基团被发现对抑制花生四烯酸5-脂氧合酶至关重要。对浓度依赖性PG生物合成效应的研究表明，CaP在较低浓度范围内增强了PG生物合成，而在较高浓度下抑制了反应。通过纯化的PG内过氧化物合成酶和微粒体PG合成酶研究了CaP对每个反应步骤的影响。CaP抑制了环氧合酶反应，同时增强了氢过氧化物酶反应。从多巴胺和脂肪酸合成了含有儿茶酚和脂溶性基团的N-酰基多巴胺，以测试它们对花生四烯酸5-脂氧合酶的抑制效果。N-亚油酰多巴胺是最活跃的化合物，在我们的测定系统中其IC50值为2.3nM，而作为5-脂氧合酶特异性抑制剂的AA 861的IC50值为8nM。
• Structure and Thermotropic Phase Behavior of a Homologous Series of Bioactive<i>N</i>-Acyldopamines
  作者：S. Thirupathi Reddy、Pradip K. Tarafdar、Ravi Kanth Kamlekar、Musti J. Swamy

  DOI：10.1021/jp402750m

  日期：2013.7.25

  N-Acyldopamines (NADAs), which are present in mammalian nervous tissues, exhibit interesting biological and pharmacological properties. In the present study, a homologous series of NADAs with varying acyl chains (n = 12-20) have been synthesized and characterized. Differential scanning calorimetric studies show that in the dry state the transition temperatures, enthalpies, and entropies of NADAs exhibit odd-even alternation with the values corresponding to the even chain length series being slightly higher. Both even and odd chain length NADAs display a linear dependence of the transition enthalpies and entropies on the chain length. However, odd-even alternation was not observed in the calorimetric properties upon hydration, although the transition enthalpies and entropies exhibit linear dependence. Linear least-squares analyses yielded incremental values contributed by each methylene group to the transition enthalpy and entropy and the corresponding end contributions. N-Lauroyldopamine (NLDA) crystallized in the monoclinic space group C2/c with eight symmetry-related molecules in the unit cell. Single-crystal X-ray diffraction studies show that NLDA molecules are organized in the bilayer form, with a head-to-head (and tail-to-tail) arrangement of the molecules. Water-mediated hydrogen bonds between the hydroxyl groups of the dopamine moieties of opposing layers and N-H center dot center dot center dot O hydrogen bonds between the amide groups of adjacent molecules in the same layer stabilize the crystal packing. These results provide a thermodynamic and structural basis for investigating the interaction of NADAs with other membrane lipids, which are expected to provide clues to understand how they function in vivo, e.g., as signaling molecules in the modulation of pain.