2'-acetoxy-4-methoxychalcone dibromide | 93868-47-4

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 直链 1,3-二芳基丙烷
• 英文名称: 2'-acetoxy-4-methoxychalcone dibromide
• 英文别名: 4-Methoxy-2'-acetoxy-chalkondibromid；1-(2-acetoxy-phenyl)-2,3-dibromo-3-(4-methoxy-phenyl)-propan-1-one；1-(2-Acetoxy-phenyl)-2,3-dibrom-3-(4-methoxy-phenyl)-propan-1-on；[2-[2,3-Dibromo-3-(4-methoxyphenyl)propanoyl]phenyl] acetate
• CAS: 93868-47-4
• 化学式: C₁₈H₁₆Br₂O₄
• 分子量: 456.131
• InChiKey: JABKRHBNAUVKIV-UHFFFAOYSA-N

物化性质

• 沸点：
  516.0±50.0 °C(Predicted)
• 密度：
  1.587±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.4
• 重原子数：
  24
• 可旋转键数：
  7
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  52.6
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2'-acetoxy-4-methoxychalcone dibromide 在 sodium methylate 、 potassium carbonate 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 生成 4--甲氧基黄酮
  参考文献：
  名称：

  An environmentally benign synthesis of aurones and flavones from 2′-acetoxychalcones using n -tetrabutylammonium tribromide

  摘要：

  A wide variety of aurones (3a-f) can be prepared exclusively from 2'-acetoxychalcones (1a-f) in high yields in two steps, by bromination using n-tetrabutylammonium tribromide (TBATB) in the presence of CaCO3 in CH2Cl2-MeOH (5:2) at 0-5 degreesC followed by cyclization of the brominated. products 2a-f on treating with 0.2 M ethanolic KOH solution at 0-5 degreesC, respectively. In contrast various flavone derivatives 6a-f can be obtained exclusively from compounds 1a-f in fairly good yields, by brominating with the same reagent in CH2Cl2, followed by dehydrobromination and finally cyclization on treating with 0.1 M NaOMe solution. (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(01)01938-4
• 作为产物：
  描述：

  2'-acetoxy-4-methoxy-trans-chalcone 在 tetra-N-butylammonium tribromide 作用下， 以 二氯甲烷 为溶剂， 以75%的产率得到2'-acetoxy-4-methoxychalcone dibromide
  参考文献：
  名称：

  An environmentally benign synthesis of aurones and flavones from 2′-acetoxychalcones using n -tetrabutylammonium tribromide

  摘要：

  A wide variety of aurones (3a-f) can be prepared exclusively from 2'-acetoxychalcones (1a-f) in high yields in two steps, by bromination using n-tetrabutylammonium tribromide (TBATB) in the presence of CaCO3 in CH2Cl2-MeOH (5:2) at 0-5 degreesC followed by cyclization of the brominated. products 2a-f on treating with 0.2 M ethanolic KOH solution at 0-5 degreesC, respectively. In contrast various flavone derivatives 6a-f can be obtained exclusively from compounds 1a-f in fairly good yields, by brominating with the same reagent in CH2Cl2, followed by dehydrobromination and finally cyclization on treating with 0.1 M NaOMe solution. (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(01)01938-4

文献信息

• Amine-effected cyclization of chalcone dihalides to aurones
  作者：John A. Donnelly、Geraldine M. Emerson

  DOI：10.1016/s0040-4020(01)87903-5

  日期：1990.1

  aurones was studied using cyclohexylamine and the most representative member of each class of these αβ-disubstituted ketones and α-halogeno chalcones. Overall yields of heterocyclic products were generally poor except from 4'6'-dimethoxy- and 3-nitro- substituted chalcone systems; aurones were obtained in fair yield from the former and in excellent yield from the latter. 22'-Diacetoxychalcone dibromide and

  研究了使用环己胺以及这些αβ-二取代酮和α-卤代查耳酮中每类中最具代表性的成员，将胺催化的αβ-二溴二氢查耳酮和α-溴查耳酮作为金刚烷的一般合成方法的可能性。除了4'6'-二甲氧基和3-硝基取代的查尔酮体系外，杂环产物的总收率通常很差。从前者中以合理的产率获得金黄色，从后者中以优异的产率获得。22'-二乙酰氧基查尔酮二溴化物和22'-二乙酰氧基-α-溴查尔酮环化成2-苯甲酰基苯并呋喃，排除了相应的金酮和黄酮。
• Bhide et al., Rasayanam, 1956, vol. 2, p. 135,139
  作者：Bhide et al.

  DOI：——

  日期：——
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  作者：Marathey

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• Herstein; v. Kostanecki, Chemische Berichte, 1899, vol. 32, p. 319
  作者：Herstein、v. Kostanecki

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• Limaye, Rasayanam, 1950, vol. 2, p. 1,5
  作者：Limaye

  DOI：——

  日期：——