methyl 3-methoxy-4-hydroxy-5-bromo-cinnamate | 146072-13-1

• 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: methyl 3-methoxy-4-hydroxy-5-bromo-cinnamate
• 英文别名: methyl (E)-3-(3-bromo-4-hydroxy-5-methoxyphenyl)prop-2-enoate
• CAS: 146072-13-1
• 化学式: C₁₁H₁₁BrO₄
• mdl: MFCD23713212
• 分子量: 287.11
• InChiKey: AQFDNNSMSPVCLF-ONEGZZNKSA-N

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：
  0.181
• 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：

  methyl 3-methoxy-4-hydroxy-5-bromo-cinnamate 在 palladium on activated charcoal copper(I) chloride 、 ammonium hydroxide 、 lithium aluminium tetrahydride 、 盐酸羟胺 、 氢气 作用下， 以 四氢呋喃 为溶剂， 反应 43.0h， 生成 2-cyclopentyl-5-(3-hydroxypropyl)-7-methoxy-benzofuran
  参考文献：
  名称：

  Regiospecific introduction of carbon-3 formyl group to 2,5-dialkyl-7-methoxy-benzo[b] furans : Synthesis of potential ligands for adenosine A1 receptors

  摘要：

  Based on the structure of 1,3-dipropyl-8-cyclopentylxanthine (CPX), the most potent adenosine A1-selective antagonist known today, two derivatives of the novel adenosine A1 receptor ligand 5-(3-hydroxpropyl)-7-methoxy-2-3'-methoxy-4'-hydroxyphenyl)-benzo[b]furan-3-carbaldehyde have been synthesized by utilizing as key steps the regiospecific introduction of a formyl group to of 2-cyclopentyl-and 2-(cyclopent-1'-en-1'-yl)-5-(3-hydroxypropyl)-7-methoxy-benzo[b]furans.

  DOI：

  10.1016/s0040-4020(01)88338-1
• 作为产物：
  描述：

  甲醇 、 3-溴-4-羟基-5-甲氧基苯丙烯酸 在 硫酸 作用下， 生成 methyl 3-methoxy-4-hydroxy-5-bromo-cinnamate
  参考文献：
  名称：

  溴和碘-阿魏酸衍生物的氧化偶联：（±）-veraguensin的合成

  摘要：

  特别参照芳基四氢萘和四氢呋喃类的木脂素的合成，研究了含卤素的阿魏酸和甲酯衍生物的酚偶联。已经合成了（±）-异二十碳烯醇二甲醚（18）和（±）-veraguensin（27）。

  DOI：

  10.1016/0040-4020(76)85006-5

文献信息

• Naturally occurring benzofuran: isolation, structure elucidation and total synthesis of 5-(3-hydroxypropyl)-7-methoxy-2-(3′-methoxy-4′-hydroxyphenyl)-3-benzo[b]furancarbaldehyde, a novel adenosine A1 receptor ligand isolated from salvia miltiorrhiza bunge (danshen)
  作者：Zhen Yang、Po Ming Hon、Kuk Ying Chui、Zun Le Xu、Hson Mou Chang、Chi Ming Lee、Yu Xin Cui、Henry N.C. Wong、Chi Duen Poon、Bing M. Fung

  DOI：10.1016/s0040-4039(00)78908-8

  日期：1991.4

  A naturally occurring benzofuran, namely 5-(3-hydroxypropyl)-7-methoxy-2-(3′-methoxy-4′-hydroxyphenyl)-3-benzo[b]furancarbaldehyde was isolated from the roots of S. miltiorrhiza Bunge “Danshen”. Its structure was established by means of spectroscopic methods as well as by a total synthesis. Both the natural and the synthetic compounds showed a high potency (IC50 = 17 nM and 10 nM, respectively) in

  从S. miltiorrhiza Bunge的根中分离出天然存在的苯并呋喃，即5-（3-羟丙基）-7-甲氧基-2-（3'-甲氧基-4'-羟基苯基）-3-苯并[ b ]呋喃甲醛。丹参”。它的结构是通过光谱方法以及通过全合成来确定的。天然化合物和合成化合物在牛腺苷A 1放射性配体结合中均显示出高效价（分别为IC 50 = 17 nM和10 nM）。
• Schreiber,F.G.; Stevenson,R., Journal of the Chemical Society. Perkin transactions I, 1976, p. 1514 - 1518
  作者：Schreiber,F.G.、Stevenson,R.

  DOI：——

  日期：——
• Regiospecific introduction of carbon-3 formyl group to 2,5-dialkyl-7-methoxy-benzo[b] furans : Synthesis of potential ligands for adenosine A1 receptors
  作者：Henry N.C. Wong、Chang Rong Niu、Zhen Yang、Po Ming Hon、Hson Mou Chang、Chi Ming Lee

  DOI：10.1016/s0040-4020(01)88338-1

  日期：1992.11

  Based on the structure of 1,3-dipropyl-8-cyclopentylxanthine (CPX), the most potent adenosine A1-selective antagonist known today, two derivatives of the novel adenosine A1 receptor ligand 5-(3-hydroxpropyl)-7-methoxy-2-3'-methoxy-4'-hydroxyphenyl)-benzo[b]furan-3-carbaldehyde have been synthesized by utilizing as key steps the regiospecific introduction of a formyl group to of 2-cyclopentyl-and 2-(cyclopent-1'-en-1'-yl)-5-(3-hydroxypropyl)-7-methoxy-benzo[b]furans.
• Oxidative coupling of bromo- and iodo-ferulic acid derivatives: synthesis of (±)-veraguensin
  作者：Riaz Ahmed、Fred G. Schreiber、Robert Stevenson、John R. Williams、Hilary M. Yeo

  DOI：10.1016/0040-4020(76)85006-5

  日期：1976.1

  The phenolic coupling of halogen-containing ferulic acid and methyl ester derivatives was examined with particular reference to the synthesis of lignans of the aryltetralin and tetrahydrofuran classes. (±)-Isolariciresinol dimethyl ether (18) and (±)-veraguensin (27) have been synthesized.

  特别参照芳基四氢萘和四氢呋喃类的木脂素的合成，研究了含卤素的阿魏酸和甲酯衍生物的酚偶联。已经合成了（±）-异二十碳烯醇二甲醚（18）和（±）-veraguensin（27）。