(E)-1-(β-D-glucopyranosyl)-4-phenyl-but-3-en-2-one | 1164131-45-6

• 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-(β-D-glucopyranosyl)-4-phenyl-but-3-en-2-one
• 英文别名: (E)-4-phenyl-1-((2S,3R,4R,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)tetrahydro-2H-pyran-2-yl)but-3-en-2-one；(E)-4-phenyl-1-[(2S,3R,4R,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]but-3-en-2-one
• CAS: 1164131-45-6
• 化学式: C₁₆H₂₀O₆
• 分子量: 308.331
• InChiKey: PCQTVJXNLYAPQD-HXEHUVJKSA-N

物化性质

• 熔点：
  175-176 °C
• 沸点：
  568.5±50.0 °C(Predicted)
• 密度：
  1.357±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -0.3
• 重原子数：
  22
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.44
• 拓扑面积：
  107
• 氢给体数：
  4
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  (E)-1-(β-D-glucopyranosyl)-4-phenyl-but-3-en-2-one 在 potassium tert-butylate 、 sodium methylate 作用下， 以 甲醇 、 二甲基亚砜 为溶剂， 反应 0.5h， 生成 3-cyano-4-phenyl-6-[(β-D-glucopyranosyl)methyl]pyridone
  参考文献：
  名称：

  新型吡喃糖基均-C-核苷的便捷合成及其抗糖尿病活性。

  摘要：

  通过在t-BuOK存在下丁烯酰基C-糖苷（5a-5j和8）与氰基乙酰胺的反应，然后进一步修饰，合成了一系列吡喃糖基-C-核苷。该反应通过将氰基乙酰胺迈克尔加成到丁烯酰基C-糖苷中，然后进行脱水环化和氧化芳构化而得到糖基甲基吡啶酮（6a-6j，7a-7j，9和10）。与POCl（3）在回流下反应的糖基甲基吡啶酮（6a-6e）以良好的产率得到了相应的糖基甲基吡啶（11a-11e和12a-12e）。筛选合成的化合物的体外α-葡萄糖苷酶，葡萄糖-6-磷酸酶和糖原磷酸化酶抑制活性。吡啶甲基甲基-C-核苷之一，化合物11d，

  DOI：

  10.1016/j.carres.2011.03.006
• 作为产物：
  描述：

  (E)-1-(2',3',4',6'-tetra-O-acetyl-β-D-glucopyranosyl)-4-phenylbut-3-en-2-one 在 甲醇 、 sodium methylate 作用下， 以65%的产率得到(E)-1-(β-D-glucopyranosyl)-4-phenyl-but-3-en-2-one
  参考文献：
  名称：

  Synthetic studies in butenonyl C-glycosides: Preparation of polyfunctional alkanonyl glycosides and their enzyme inhibitory activity

  摘要：

  A simple synthesis of phenyl butenoyl C-glycosides has been achieved by Aldol condensation of peracetylated glycosyl acetones with aromatic aldehydes followed by deacetylation with methanolic NaOMe. The selected butenoyl C-glycosides on conjugate addition of diethyl malonate resulted in polyfunctional alkanonyl glycosides in good yields. The butenoyl C- and alkanoyl C- glycosides were evaluated for their alpha-glucosidase, glucose-6-phosphatse and glycogen phosphorylase enzyme inhibitory activities in vitro. Three of the synthesized (3, 5 and 9) showed potent enzyme inhibitory activities as compared to standard drugs. Compounds 3, 5 and 9 were evaluated in vivo too displaying significant activity as compared to standard drugs acarbose and metformin. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2009.03.136

文献信息

• Compositions and Methods for Reducing Enones to Saturated Alcohols
  申请人：YALE UNIVERSITY

  公开号：US20210163384A1

  公开（公告）日：2021-06-03

  The invention relates to novel, scalable synthetic routes that allow for direct reduction of enones to the corresponding saturated alcohols. The invention relates, in certain aspects, to synthetic routes that allow for the reduction of enones to the corresponding ketones. Such reactions take place under mild conditions, are compatible with a wide range of functional groups, and expand the repertoire of existing green chemistry methodology. In certain embodiments, the reactions are run in aqueous solvent.

  本发明涉及一种新颖的可扩展的合成路线，允许将烯酮直接还原为相应的饱和醇。本发明在某些方面涉及合成路线，允许将烯酮还原为相应的酮。这样的反应在温和条件下进行，与广泛的官能团兼容，并扩展了现有绿色化学方法的技术。在某些实施例中，反应在水溶剂中进行。
• Diversity Oriented Synthesis of Pyran Based Polyfunctional Stereogenic Macrocyles and Their Conformational Studies
  作者：Arya Ajay、Shrikant Sharma、Munna Prasad Gupt、Vikas Bajpai、Hamidullah、Brijesh Kumar、Mahabir Prasad Kaushik、Rituraj Konwar、Ravi Sankar Ampapathi、Rama Pati Tripathi

  DOI：10.1021/ol3022275

  日期：2012.9.7

  A new approach to synthesize a homologous series of 14-, 15-, and 16-membered drug-like, macrocyclic glycoconjugates involving TBAHS promoted azide-propenone intramolecular cycloaddition in designed C-glycopyranosyl butenones from a simple sugar D-glucose and D-mannose is reported.
• One pot protecting group free synthesis of multifunctional biphenyl methyl-C-β-d-glycosides in aqueous medium
  作者：Mridul Misra、Rahul Sharma、Ruchir Kant、P.R. Maulik、R.P. Tripathi

  DOI：10.1016/j.tet.2010.11.067

  日期：2011.1

  One pot synthesis of the butenonyl-C-beta-D-glycosides with malononitrile in the presence of K2CO3 in water under mild and green reaction conditions leading to the formation of small library of multifunctional biphenyl methyl-C-beta-D-glycosides in good yields has been reported. The reaction is equally applicable with the substrates having different glycosyl pyranoses and aromatic rings with different substituents. (C) 2010 Elsevier Ltd. All rights reserved.
• A convenient synthesis of novel pyranosyl homo-C-nucleosides and their antidiabetic activities
  作者：Surendra Singh Bisht、Natasha Jaiswal、Anindra Sharma、Seerat Fatima、Rahul Sharma、Neha Rahuja、A.K. Srivastava、Vikas Bajpai、Brijesh Kumar、Rama P. Tripathi

  DOI：10.1016/j.carres.2011.03.006

  日期：2011.7

  A series of pyranosyl homo-C-nucleosides have been synthesized by reaction of butenonyl C-glycosides (5a-5j, and 8) and cyanoacetamide in presence of t-BuOK followed by further modifications. The reaction proceeds by Michael addition of cyanoacetamide to the butenonyl C-glycosides and subsequent dehydrative cyclization and oxidative aromatization to give glycosylmethyl pyridones (6a-6j, 7a-7j, 9, and

  通过在t-BuOK存在下丁烯酰基C-糖苷（5a-5j和8）与氰基乙酰胺的反应，然后进一步修饰，合成了一系列吡喃糖基-C-核苷。该反应通过将氰基乙酰胺迈克尔加成到丁烯酰基C-糖苷中，然后进行脱水环化和氧化芳构化而得到糖基甲基吡啶酮（6a-6j，7a-7j，9和10）。与POCl（3）在回流下反应的糖基甲基吡啶酮（6a-6e）以良好的产率得到了相应的糖基甲基吡啶（11a-11e和12a-12e）。筛选合成的化合物的体外α-葡萄糖苷酶，葡萄糖-6-磷酸酶和糖原磷酸化酶抑制活性。吡啶甲基甲基-C-核苷之一，化合物11d，
• Synthetic studies in butenonyl C-glycosides: Preparation of polyfunctional alkanonyl glycosides and their enzyme inhibitory activity
  作者：Surendra Singh Bisht、Seerat Fatima、Akhilesh K. Tamrakar、Neha Rahuja、Natasha Jaiswal、Arvind K. Srivastava、Rama P. Tripathi

  DOI：10.1016/j.bmcl.2009.03.136

  日期：2009.5

  A simple synthesis of phenyl butenoyl C-glycosides has been achieved by Aldol condensation of peracetylated glycosyl acetones with aromatic aldehydes followed by deacetylation with methanolic NaOMe. The selected butenoyl C-glycosides on conjugate addition of diethyl malonate resulted in polyfunctional alkanonyl glycosides in good yields. The butenoyl C- and alkanoyl C- glycosides were evaluated for their alpha-glucosidase, glucose-6-phosphatse and glycogen phosphorylase enzyme inhibitory activities in vitro. Three of the synthesized (3, 5 and 9) showed potent enzyme inhibitory activities as compared to standard drugs. Compounds 3, 5 and 9 were evaluated in vivo too displaying significant activity as compared to standard drugs acarbose and metformin. (C) 2009 Elsevier Ltd. All rights reserved.