7-(tert-butyldimethylsilyloxy)-5-hydroxy-3-(4-hydroxyphenyl)-4H-chromen-4-one

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 异黄酮类化合物
• 英文名称: 7-(tert-butyldimethylsilyloxy)-5-hydroxy-3-(4-hydroxyphenyl)-4H-chromen-4-one
• 英文别名: 7-O-(tert-butyldimethylsilyl)genistein；7-O-tert-butyldimethylsilylgenistein；IFG8；7-[Tert-butyl(dimethyl)silyl]oxy-5-hydroxy-3-(4-hydroxyphenyl)chromen-4-one
• 化学式: C₂₁H₂₄O₅Si
• 分子量: 384.504
• InChiKey: PBQKXDQLUUHLTK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.26
• 重原子数：
  27
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  76
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  染料木素 以 甲醇 、 二氯甲烷 、 水 为溶剂， 反应 16.0h， 生成 7-(tert-butyldimethylsilyloxy)-5-hydroxy-3-(4-hydroxyphenyl)-4H-chromen-4-one
  参考文献：
  名称：

  X-ray and 13C CP MAS investigations of structure of two genistein derivatives

  摘要：

  Structural and spectroscopic properties of two distinctly different derivatives of genistein (1), ionic and covalent, engaging the most acidic of its three phenolic functions, have been investigated. Both the 7-O-silyl ether (2), and ammonium salt (3), are stable solids, considered to be useful intermediates for achieving further chemical transformations in a manner securing highly regioselective outcome. It turned out that these two molecules contain genistein structural fragment involved in many intra- and intermolecular hydrogen bonds. In the case of 2, some infinite chains of coupled intra- and intermolecular hydrogen bonds are formed supported by hydrogen bonding to water molecules. In the structure of 3, a helical arrangement of genistein moieties is formed with the cations kept in voids. Single crystal X-ray diffraction shows that the aromatic ring B in both structures is rotated with respect to the AC fused rings of the chromenone moiety by ca. 36degrees (2) and 50degrees (3). Both new compounds crystallise as monohydrates. The number of peaks observed in the solid-state C-13 spectra of 2 and 3 corresponds to the number of magnetically non-equivalent carbons and it is in satisfactory agreement with the X-ray crystal structures of both genistein derivatives. (C) 2004 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.molstruc.2004.03.015

文献信息

• Synthesis of Selectively Protected Genistein Derivatives
  作者：Wiesław Szeja、Gabriela Pastuch、Ilona Wandzik、Nikodem Kuźnik、Grzegorz Grynkiewicz

  DOI：10.1081/scc-120026353

  日期：2003.12.1

  Differential functionalization of the phenolic groups in Genistein by sequential silylation/acylation reactions, involving some unexpected regioselective O-silyl group replacement, is described.
• X-ray and 13C CP MAS investigations of structure of two genistein derivatives
  作者：Grzegorz Grynkiewicz、Oliwia Zegrocka-Stendel、Wiesław Pucko、Jan Ramza、Anna Kościelecka、Wacław Kołodziejski、Krzysztof Woźniak

  DOI：10.1016/j.molstruc.2004.03.015

  日期：2004.6

  Structural and spectroscopic properties of two distinctly different derivatives of genistein (1), ionic and covalent, engaging the most acidic of its three phenolic functions, have been investigated. Both the 7-O-silyl ether (2), and ammonium salt (3), are stable solids, considered to be useful intermediates for achieving further chemical transformations in a manner securing highly regioselective outcome. It turned out that these two molecules contain genistein structural fragment involved in many intra- and intermolecular hydrogen bonds. In the case of 2, some infinite chains of coupled intra- and intermolecular hydrogen bonds are formed supported by hydrogen bonding to water molecules. In the structure of 3, a helical arrangement of genistein moieties is formed with the cations kept in voids. Single crystal X-ray diffraction shows that the aromatic ring B in both structures is rotated with respect to the AC fused rings of the chromenone moiety by ca. 36degrees (2) and 50degrees (3). Both new compounds crystallise as monohydrates. The number of peaks observed in the solid-state C-13 spectra of 2 and 3 corresponds to the number of magnetically non-equivalent carbons and it is in satisfactory agreement with the X-ray crystal structures of both genistein derivatives. (C) 2004 Elsevier B.V. All rights reserved.