(E)-1-(4,6-O-butylidene-β-D-glucopyranosyl)-4-(5-bromo-3-pyridyl)but-3-en-2-one | 1334710-62-1

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (E)-1-(4,6-O-butylidene-β-D-glucopyranosyl)-4-(5-bromo-3-pyridyl)but-3-en-2-one
• 英文别名: (E)-1-[(4aR,6S,7R,8R,8aS)-7,8-dihydroxy-2-propyl-4,4a,6,7,8,8a-hexahydropyrano[3,2-d][1,3]dioxin-6-yl]-4-(5-bromopyridin-3-yl)but-3-en-2-one
• CAS: 1334710-62-1
• 化学式: C₁₉H₂₄BrNO₆
• 分子量: 442.307
• InChiKey: XYQGQGJIDOXUHY-BISWRYNVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.1
• 重原子数：
  27
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.58
• 拓扑面积：
  98.1
• 氢给体数：
  2
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  (E)-1-(4,6-O-butylidene-β-D-glucopyranosyl)-4-(5-bromo-3-pyridyl)but-3-en-2-one 在 hydrazine hydrate 作用下， 以 乙醇 为溶剂， 反应 3.0h， 以81%的产率得到5-(5-bromo-3-pyridyl)-3-(4,6-O-butylidene-β-D-glucopyranosylmethyl)-1H-pyrazole
  参考文献：
  名称：

  A facile synthesis of sugar-pyrazole derivatives

  摘要：

  A facile synthesis of sugar-pyrazole derivatives has been accomplished by condensation of sugar-chalcone with hydrazine hydrate under neutral conditions resulting in yields of 70-85%. The products are characterized by FTIR and NMR spectroscopy and by elemental analysis. The beta-anomeric forms for these derivatives were assigned by NMR spectroscopy. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.carres.2011.06.019
• 作为产物：
  描述：

  4,6-O-(1-butylidene)-D-glucopyranose 在 四氢吡咯 、 sodium carbonate 作用下， 以 四氢呋喃 、 二氯甲烷 、 水 为溶剂， 生成 (E)-1-(4,6-O-butylidene-β-D-glucopyranosyl)-4-(5-bromo-3-pyridyl)but-3-en-2-one
  参考文献：
  名称：

  A facile synthesis of sugar-pyrazole derivatives

  摘要：

  A facile synthesis of sugar-pyrazole derivatives has been accomplished by condensation of sugar-chalcone with hydrazine hydrate under neutral conditions resulting in yields of 70-85%. The products are characterized by FTIR and NMR spectroscopy and by elemental analysis. The beta-anomeric forms for these derivatives were assigned by NMR spectroscopy. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.carres.2011.06.019

文献信息

• Design, synthesis and gelation studies of 4,6-O-butylidene-α,β-unsaturated-β-C-glycosidic ketones: application to plant tissue culture
  作者：Subbiah Nagarajan、Thangamuthu Mohan Das、Pandian Arjun、Nanjian Raaman

  DOI：10.1039/b902064k

  日期：——

  A series of α,β-unsaturated-β-C-glycosidic ketones was synthesized starting from D-glucose in three steps. 4,6-O-Butylidene-β-C-glycosidic ketones on aldol condensation with aromatic and heteroaromatic aldehydes in the presence of a suitable organocatalyst led to the stereoselective formation of the products in good yield. Hydrogen bonding and π–π stacking of these derivatives were established by single-crystal XRD. The soft material derived from this method had a diameter of 10–200 nm with a three-dimensional network, as determined by SEM and HR-TEM. In the present study, we discuss the mechanism of formation of these self-assembled nanostructures, the morphology of the soft material and its thermal stability. We also demonstrate the utility of these soft materials in the field of plant tissue culture.

  一系列α,β-不饱和β-C-糖苷酮是从D-葡萄糖出发，通过三步合成而成。4,6-O-丁叉基-β-C-糖苷酮与芳香族和杂芳香族醛在适当的有机催化剂存在下进行醇缩合反应，选择性地形成产物且产率良好。通过单晶XRD确立了这些衍生物的氢键和π-π堆积。该方法得到的软材料直径在10至200纳米之间，具有三维网络结构，经过SEM和HR-TEM的测定。在本研究中，我们讨论了这些自组装纳米结构的形成机制、软材料的形态及其热稳定性。我们还展示了这些软材料在植物组织培养领域的应用价值。
• An Easy Access to Novel Sugar-Based Spirooxindole-pyrrolidines or -pyrrolizidines through [3+2] Cycloaddition of Azomethine Ylides
  作者：Thangamuthu Das、Arasappan Hemamalini、Subbiah Nagarajan、Pawar Ravinder、Venkatesan Subramanian

  DOI：10.1055/s-0030-1260111

  日期：2011.8

  An efficient one-pot synthesis of a library of novel sugar-based spirooxindole-pyrrolidines or -pyrrolizidines has been accomplished by [3+2] cycloaddition. This method utilizes an azo­methine ylide derived from isatin and sarcosine or l-proline with an α,β-unsaturated β-C-glycosidic ketone as the dipolarophile. All these sugar-based heterocyclics were characterized by NMR (¹H and ¹³C), HPLC, and elemental analysis

  通过[3+2]环加成成功实现了一种高效的一锅合成新型糖基螺氧喹啉-吡咯烷或-吡咯啉的化合物库。这种方法利用了来源于异靛和肌氨酸或l-脯氨酸的偶氮甲烯耦合物，以及作为极性合物的α,β-不饱和β-C-糖苷酮。所有这些糖基杂环化合物均通过核磁共振（¹H和¹³C）、高效液相色谱（HPLC）和元素分析进行了表征。
• A facile synthesis of sugar-pyrazole derivatives
  作者：Arasappan Hemamalini、Subbiah Nagarajan、Thangamuthu Mohan Das

  DOI：10.1016/j.carres.2011.06.019

  日期：2011.9

  A facile synthesis of sugar-pyrazole derivatives has been accomplished by condensation of sugar-chalcone with hydrazine hydrate under neutral conditions resulting in yields of 70-85%. The products are characterized by FTIR and NMR spectroscopy and by elemental analysis. The beta-anomeric forms for these derivatives were assigned by NMR spectroscopy. (C) 2011 Elsevier Ltd. All rights reserved.