(E)-4-(4-methoxyphenyl)-1-(3,4,5-trihydroxytetrahydro-2H-pyran-2-yl)but-3-en-2-one | 1173597-31-3

• 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)-4-(4-methoxyphenyl)-1-(3,4,5-trihydroxytetrahydro-2H-pyran-2-yl)but-3-en-2-one
• 英文别名: (E)-4-(4-methoxyphenyl)-1-[(2S,3R,4S,5R)-3,4,5-trihydroxyoxan-2-yl]but-3-en-2-one
• CAS: 1173597-31-3
• 化学式: C₁₆H₂₀O₆
• 分子量: 308.331
• InChiKey: ASIWJRSZKQPCIM-BRWWLDDYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.2
• 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：
  96.2
• 氢给体数：
  3
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  (E)-4-(4-methoxyphenyl)-1-(3,4,5-trihydroxytetrahydro-2H-pyran-2-yl)but-3-en-2-one 、 丙二腈 在 氧气 、 potassium carbonate 作用下， 以 水 为溶剂， 以75%的产率得到3-amino-4'-methoxy-5-[(β-D-xylopyranosyl)methyl]biphenyl-2,4-dicarbonitrile
  参考文献：
  名称：

  One pot protecting group free synthesis of multifunctional biphenyl methyl-C-β-d-glycosides in aqueous medium

  摘要：

  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.

  DOI：

  10.1016/j.tet.2010.11.067
• 作为产物：
  描述：

  4-甲氧基苯甲醛 、 4,8-anhydro-1,3-dideoxy-D-gulo-octulose 在 三乙胺 、 L-脯氨酸 作用下， 以 甲醇 为溶剂， 反应 28.0h， 以98%的产率得到(E)-4-(4-methoxyphenyl)-1-(3,4,5-trihydroxytetrahydro-2H-pyran-2-yl)but-3-en-2-one
  参考文献：
  名称：

  脯氨酸-TEA催化通过新途径从酮和芳香醛中直接合成新颖高效的醛醇缩合反应

  摘要：

  在室温下于甲醇中，通过1-脯氨酸-TEA（三乙胺）催化从各种酮和多种醛中合成的新颖高效的直接羟醛缩合反应，从而以优异的收率得到相应的（E）-α，β-不饱和酮。通过使用该方法，从未改性的酮C-糖苷和醛中获得了一些复杂的（E）-α，β-不饱和酮C-糖苷。该反应通过新的途径进行，其中捕获并鉴定了特定的中间体。

  DOI：

  10.1016/j.tet.2009.04.052

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。
• A novel and efficient direct aldol condensation from ketones and aromatic aldehydes catalyzed by proline–TEA through a new pathway
  作者：Jun-feng Wang、Meng Lei、Qin Li、Ze-mei Ge、Xin Wang、Run-tao Li

  DOI：10.1016/j.tet.2009.04.052

  日期：2009.6

  aldol condensation from various ketones and a wide range of aldehydes was catalyzed by l-proline–TEA (triethylamine) in MeOH at room temperature, affording the corresponding (E)-α,β-unsaturated ketones in excellent yields. By using the method, some complicated (E)-α,β-unsaturated ketone C-glycosides were obtained from unmodified ketone C-glycosides and aldehydes. This reaction proceeds through a new

  在室温下于甲醇中，通过1-脯氨酸-TEA（三乙胺）催化从各种酮和多种醛中合成的新颖高效的直接羟醛缩合反应，从而以优异的收率得到相应的（E）-α，β-不饱和酮。通过使用该方法，从未改性的酮C-糖苷和醛中获得了一些复杂的（E）-α，β-不饱和酮C-糖苷。该反应通过新的途径进行，其中捕获并鉴定了特定的中间体。
• 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.