3-甲氧基-4-羟基-5-溴肉桂酸甲酯 | 61222-88-6

• 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
• 中文名称: 3-甲氧基-4-羟基-5-溴肉桂酸甲酯
• 英文名称: methyl 3-methoxy-4-hydroxy-5-bromocinnamate
• 英文别名: 3-Methoxy-4-hydroxy-5-brom-zimtsaeuremethylester；Methyl 3-(3-bromo-4-hydroxy-5-methoxyphenyl)prop-2-enoate；methyl 3-(3-bromo-4-hydroxy-5-methoxyphenyl)prop-2-enoate
• CAS: 61222-88-6
• 化学式: C₁₁H₁₁BrO₄
• 分子量: 287.11
• InChiKey: AQFDNNSMSPVCLF-UHFFFAOYSA-N

物化性质

• 熔点：
  112-113 °C(Solv: methanol (67-56-1))
• 沸点：
  352.3±42.0 °C(Predicted)
• 密度：
  1.518±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  16
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  55.8
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  3-甲氧基-4-羟基-5-溴肉桂酸甲酯 在 palladium on activated charcoal 吡啶 、 盐酸 、 ammonium hydroxide 、 sodium hydroxide 、 lithium aluminium tetrahydride 、 potassium chloride 、 盐酸羟胺 、 氢气 、 copper(II) sulfate 作用下， 以 四氢呋喃 、 甲醇 、 水 、 丙酮 为溶剂， 反应 69.17h， 生成 5-(3-hydroxypropyl)-7-methoxy-3-methyl-2-(3'-methoxy-4'-hydroxyphenyl)benzofuran
  参考文献：
  名称：

  Compounds from Danshen. Part 7. Regioselective introduction of carbon-3 substituents to 5-alkyl-7-methoxy-2-phenylbenzo[b]furans: synthesis of a novel adenosine A1 receptor ligand and its derivatives

  摘要：

  By maintaining the balance between the electronic requirements, the stereochemical restrictions as well as the kinetic and thermodynamic factors, the unprecedented regioselective electrophilic aromatic substitution of formyl and nitro groups to carbon-3 of 5-alkyl-7-methoxy-2-phenylbenzo[b]furans have been achieved. Subsequent transformation of the resulting formyl group into methyl, hydroxymethyl, 1-hydroxyethyl, and cyano groups are also described.

  DOI：

  10.1021/jo00052a046
• 作为产物：
  描述：

  甲基丙二酸氢 、 5-溴香兰素 在 哌啶 、 吡啶 作用下， 生成 3-甲氧基-4-羟基-5-溴肉桂酸甲酯
  参考文献：
  名称：

  Hellmann,H.; Elser,W., Justus Liebigs Annalen der Chemie, 1961, vol. 639, p. 77 - 88

  摘要：

  DOI：

文献信息

• Composition Containing Styraxlignolide A or the Aglycone Thereof as an Active Ingredient for Preventing or Treating Asthma
  申请人：Ahn Kyung Seop

  公开号：US20130244959A1

  公开（公告）日：2013-09-19

  The present invention relates to a pharmaceutical composition for preventing or treating asthma, the composition containing styraxlignolide A or an aglycone thereof as an active ingredient. More particularly, styraxlignolide A compound is one separated from stems and barks of Styrax japonica , and styraxlignolide A or homoegonol, which is an aglycone of styraxlignolide A and which has improved safety, has the effect of attenuating weight loss and airway hyperresponsiveness, inhibiting the generation of reactive oxygen species in airway, inhibiting generation of IgE, TGF-β1, and IL-17 in the serum and bronchoalveolar lavage fluid, inhibiting endobronchial inflammatory cell infiltration, and inhibiting the formation of a mucous plug and subepithelial fibrosis in an asthma-induced mouse model. Therefore, styraxlignolide or homoegonol can be effectively used as the active ingredient of a pharmaceutical composition for preventing or treating bronchial asthma in which airway remodeling has progressed.

  本发明涉及一种用于预防或治疗哮喘的药物组合物，该组合物含有styraxlignolide A或其去糖苷作为活性成分。更具体地说，styraxlignolide A化合物是从日本安息香的茎和树皮中分离出来的，styraxlignolide A或homoegonol，后者是styraxlignolide A的一个去糖苷，具有改善安全性的效果，具有减轻体重减少和气道高反应性、抑制气道内活性氧种的生成、抑制血清和支气管肺泡灌洗液中IgE、TGF-β1和IL-17的生成、抑制支气管内炎症细胞浸润、抑制黏液栓和支气管黏膜下纤维化在哮喘诱导小鼠模型中的形成。因此，styraxlignolide或homoegonol可以有效地用作预防或治疗气道重塑已进展的支气管哮喘的药物组合物的活性成分。
• Hellmann,H.; Elser,W., Justus Liebigs Annalen der Chemie, 1961, vol. 639, p. 77 - 88
  作者：Hellmann,H.、Elser,W.

  DOI：——

  日期：——
• Compounds from Danshen. Part 7. Regioselective introduction of carbon-3 substituents to 5-alkyl-7-methoxy-2-phenylbenzo[b]furans: synthesis of a novel adenosine A1 receptor ligand and its derivatives
  作者：Zhen Yang、Han Biao Liu、Chi Ming Lee、Hson Mou Chang、Henry N. C. Wong

  DOI：10.1021/jo00052a046

  日期：1992.12

  By maintaining the balance between the electronic requirements, the stereochemical restrictions as well as the kinetic and thermodynamic factors, the unprecedented regioselective electrophilic aromatic substitution of formyl and nitro groups to carbon-3 of 5-alkyl-7-methoxy-2-phenylbenzo[b]furans have been achieved. Subsequent transformation of the resulting formyl group into methyl, hydroxymethyl, 1-hydroxyethyl, and cyano groups are also described.