(E)-1-(4,6-O-butylidene-β-D-glucopyranosyl)-4-(3,4-dioxanephenyl)but-3-en-2-one | 1334710-61-0

• 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
• 英文名称: (E)-1-(4,6-O-butylidene-β-D-glucopyranosyl)-4-(3,4-dioxanephenyl)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-(1,3-benzodioxol-5-yl)but-3-en-2-one
• CAS: 1334710-61-0
• 化学式: C₂₁H₂₆O₈
• 分子量: 406.433
• InChiKey: ADWRFJZLBFRKCY-TVUBTIPGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.3
• 重原子数：
  29
• 可旋转键数：
  6
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.57
• 拓扑面积：
  104
• 氢给体数：
  2
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  (E)-1-(4,6-O-butylidene-β-D-glucopyranosyl)-4-(3,4-dioxanephenyl)but-3-en-2-one 在 sodium acetate 作用下， 以 甲苯 、 乙腈 为溶剂， 反应 5.0h， 生成 trans-4-[3,4-(methylenedioxy)phenyl]-3-[2-(2,3-di-O-acetyl-4,6-O-butylidene-β-D-glucopyranosyl)-1-oxoethyl]-1-methylpyrrolidine
  参考文献：
  名称：

  通过[3 + 2]环加成法可轻松获得基于糖的N-甲基-吡咯烷的合成

  摘要：

  糖基N-甲基-吡咯烷衍生物是通过肌氨酸和多聚甲醛产生的叶​​立德与糖衍生的双极性亲和剂的环加成反应合成的。所有新合成的产物均通过NMR（1 H，13 C），质谱和元素分析进行表征。

  DOI：

  10.1002/jhet.2398
• 作为产物：
  描述：

  胡椒醛 、 (4,6-O-butylidene-β-D-glucopyranosyl)propan-2-one 在 四氢吡咯 作用下， 以 二氯甲烷 为溶剂， 生成 (E)-1-(4,6-O-butylidene-β-D-glucopyranosyl)-4-(3,4-dioxanephenyl)but-3-en-2-one
  参考文献：
  名称：

  An Easy Access to Novel Sugar-Based Spirooxindole-pyrrolidines or -pyrrolizidines through [3+2] Cycloaddition of Azomethine Ylides

  摘要：

  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。

  DOI：

  10.1055/s-0030-1260111

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。
• A concise pathway to synthesize a novel class of pyrido(2,3-d)pyrimidine-C-β-d-glycosides
  作者：Muniyappapillai Jeganathan Shanmugam、Thangamuthu Mohan Das

  DOI：10.1016/j.carres.2012.11.013

  日期：2013.3

  A concise pathway to synthesize a novel class of nine different pyrido(2,3-d)pyrimidine-C-beta-D-glycosides is reported. Formation of Michael adduct as an intermediate followed by heterocyclization are the key steps and the products were characterized by different spectral studies. beta-Anomeric forms of C-glycosides were assigned from H-1 NMR spectroscopy. (C) 2012 Elsevier Ltd. All rights reserved.
• An Easy Access to the Synthesis of Sugar-Based<i>N</i>-Methyl-Pyrrolidine via [3 + 2] Cycloaddition Methodology
  作者：Hemamalini Arasasppan、Mohan Das Thangamuthu

  DOI：10.1002/jhet.2398

  日期：2016.1

  Sugar‐based N‐methyl‐pyrrolidine derivatives have been synthesized by the cycloaddition reaction of the ylide generated from sarcosine and paraformaldehyde with the sugar‐derived dipolarophile. All the newly synthesized products were characterized by NMR (1H, 13C), mass spectroscopy and elemental analysis.

  糖基N-甲基-吡咯烷衍生物是通过肌氨酸和多聚甲醛产生的叶​​立德与糖衍生的双极性亲和剂的环加成反应合成的。所有新合成的产物均通过NMR（1 H，13 C），质谱和元素分析进行表征。
• 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。