4-methyl-7-hydroxyflavylium chloride | 20921-29-3

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 黄酮类化合物
• 英文名称: 4-methyl-7-hydroxyflavylium chloride
• 英文别名: 7-hydroxy-4-methylflavylium chloride；4-Methyl 7-hydroxyflavylium chloride；4-methyl-2-phenylchromenylium-7-ol;chloride
• CAS: 20921-29-3
• 化学式: C₁₆H₁₃O₂*Cl
• 分子量: 272.731
• InChiKey: ZQUVXAZUSKAMHV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  19
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.06
• 拓扑面积：
  21.2
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  4-methyl-7-hydroxyflavylium chloride 在 水 作用下， 生成 4-Methyl-2-phenyl-2,4a-dihydro-chromen-7-one
  参考文献：
  名称：

  Kinetics of ultra-fast excited state proton transfer from 7-hydroxy-4-methylflavylium chloride to water

  摘要：

  Excited state proton transfer from 7-hydroxy-4-methylflavylium chloride to water is reported. From a modified analysis of picosecond time-resolved fluorescence data (not using the lifetime of a parent compound), all rate constants were determined: the deprotonation rate constant of the flavylium cation, k(d) = 1.4 x 10(11) s(-1), the protonation rate constant of the base form, k(p) = 2.3 x 10(10) l mol(-1) s(-1) and the reciprocal fluorescence lifetimes of these species, k(AH+) = 7.8 x 10(9) s(-1) (tau(AH+) = 128 ps) and k(A) = 7.6 x 10(9) s(-1) (tau(A) = 132 ps), in water, at 20 degrees C. The value of k(d) is the largest measured value for an intermolecular proton transfer (to water). (C) 1998 Elsevier Science B.V. All rights reserved.

  DOI：

  10.1016/s0009-2614(98)01199-3
• 作为产物：
  描述：

  4-Methyl-2-phenyl-2,4a-dihydro-chromen-7-one 在 oxonium 作用下， 生成 4-methyl-7-hydroxyflavylium chloride
  参考文献：
  名称：

  Kinetics of ultra-fast excited state proton transfer from 7-hydroxy-4-methylflavylium chloride to water

  摘要：

  Excited state proton transfer from 7-hydroxy-4-methylflavylium chloride to water is reported. From a modified analysis of picosecond time-resolved fluorescence data (not using the lifetime of a parent compound), all rate constants were determined: the deprotonation rate constant of the flavylium cation, k(d) = 1.4 x 10(11) s(-1), the protonation rate constant of the base form, k(p) = 2.3 x 10(10) l mol(-1) s(-1) and the reciprocal fluorescence lifetimes of these species, k(AH+) = 7.8 x 10(9) s(-1) (tau(AH+) = 128 ps) and k(A) = 7.6 x 10(9) s(-1) (tau(A) = 132 ps), in water, at 20 degrees C. The value of k(d) is the largest measured value for an intermolecular proton transfer (to water). (C) 1998 Elsevier Science B.V. All rights reserved.

  DOI：

  10.1016/s0009-2614(98)01199-3

文献信息

• Synthetic dyes: simple and original ways to 4-substituted flavylium salts and their corresponding vitisin derivatives
  作者：Christine Roehri-Stoeckel、Emmanuel Gonzalez、André Fougerousse、Raymond Brouillard

  DOI：10.1139/v01-089

  日期：2001.7.1

  Flavylium salts substituted at the 4-position have been prepared according to a Grignard reaction of some flavones with appropriate alkyl- and aryl-magnesium bromides. Among these compounds, 4-methyl flavylium salts were gently reacted with aromatic aldehydes, affording new anthocyanidin pigments, some of which are of the vitisin family. These are the first examples of chemically synthesized vitisidins (aglycones of vitisins). Compared to the more common flavylium salts, they demonstrate a large bathochromic shift (from about 100–200 nm), thus providing blue-violet and green colours, so difficult to obtain with anthocyanidins in general.Key words: 4-substituted flavylium chlorides, vitisin aglycones, blue-violet and green anthocyanidin pigments.

  在某些黄酮类化合物与适当的烷基和芳基溴化镁发生格氏反应的情况下，制备了在4位取代的黄红盐。在这些化合物中，4-甲基黄红盐与芳香醛轻柔地反应，形成了新的花青素色素，其中一些属于vitisin家族。这些是化学合成的vitisidins（vitisins的无糖基）的首次实例。与更常见的黄红盐相比，它们表现出较大的巴托克移位（约100-200纳米），从而提供了蓝紫色和绿色，这在一般花青素中很难获得。关键词：4-取代黄红盐，vitisin无糖基，蓝紫色和绿色花青素色素。
• Kationische Farbstoffe, Verfahren zu deren Herstellung und diese Verbindungen enthaltende Färbemittel
  申请人：Wella Aktiengesellschaft

  公开号：EP1489142A1

  公开（公告）日：2004-12-22

  Die vorliegende Erfindung betrifft Verbindungen der Formel (V), ein Verfahren zu deren Herstellung sowie die Verbindungen der Formel (V) enthaltende Färbemittel.

  本发明涉及式（V）化合物、其制备工艺以及含有式（V）化合物的着色剂。
• 1-benzopyrane-derivatives and colouring agents containing the salts thereof
  申请人：——

  公开号：US20030196281A1

  公开（公告）日：2003-10-23

  The present invention concerns an agent for coloring fibers that is obtained by mixing two components—if necessary with the addition of an alkalinizing agent or an acid—said agent being characterized in that one component (component A2) contains at least one electrophilic compound and the other component (component A1) contains at least one 1-benzopyran of formula (Ia)/(Ib) or a 1-benzopyrylium derivative of formula (I), 1 and a method for temporarily coloring keratin fibers whereby the hair is first colored with the aforesaid coloring agent and then, at any future time, is again decolorized with a reducing agent.

  本发明涉及一种纤维着色剂，该着色剂由两种组分混合而成，必要时加入碱化剂或酸，其特征在于其中一种组分（组分 A2）含有至少一种亲电化合物，另一种组分（组分 A1）含有至少一种式 (Ia)/(Ib) 的 1-苯并吡喃或式 (I) 的 1-苯并吡喃衍生物、 1 以及一种对角蛋白纤维进行临时着色的方法，首先用上述着色剂对头发进行着色，然后，在以后的任何时间，再用还原剂对头发进行脱色。
• Brockmann et al., Chemische Berichte, 1944, vol. 77/79, p. 529,533
  作者：Brockmann et al.

  DOI：——

  日期：——
• KATIONISCHE FARBSTOFFE, VERFAHREN ZU DEREN HERSTELLUNG UND DIESE VERBINDUNGEN ENTHALTENDE FÄRBEMITTEL
  申请人：Wella Aktiengesellschaft

  公开号：EP1397435A1

  公开（公告）日：2004-03-17