(E)-3-(5-chloro-2-hydroxyphenyl)acrylic acid

• 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: (E)-3-(5-chloro-2-hydroxyphenyl)acrylic acid
• 英文别名: (E)-3-(5-chloro-2-hydroxyphenyl)prop-2-enoic acid
• 化学式: C₉H₇ClO₃
• 分子量: 198.606
• InChiKey: LRXNDAUSLCBSTK-DAFODLJHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  13
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  57.5
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (E)-3-(5-chloro-2-hydroxyphenyl)acrylic acid 、 sodium 4-fluorobenzenesulfinate 在 copper(II) choride dihydrate 、 silver trifluoroacetate 、 caesium carbonate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 24.0h， 以47%的产率得到5-chloro-2-[(4-fluorophenyl)sulfonyl]benzofuran
  参考文献：
  名称：

  Copper/Silver-Mediated Cascade Reactions for the Construction of 2-Sulfonylbenzo[b]furans from trans-2-Hydroxycinnamic Acids and Sodium Sulfinates

  摘要：

  Efficient construction of 2-sulfonylbenzo[b]furans is achieved from readily available trans-2-hydroxycinnamic acids and sodium sulfinates mediated by the CuCl2 center dot 2H(2)O/AgTFA system under mild conditions. This unprecedented synthetic protocol provides expedient access to a series of products in one step via a protodecarboxylation/C-S bond formation/C-O bond formation cascade.

  DOI：

  10.1021/jo4024478
• 作为产物：
  描述：

  4-chlorophenyl diethylcarbamate 在 silver hexafluoroantimonate 、 lithium hydroxide monohydrate 、 [RuCl2(p-cymene)]2 、 copper(II) acetate monohydrate 作用下， 以 四氢呋喃 、 甲醇 、 乙二醇二甲醚 、 水 为溶剂， 反应 36.0h， 生成 (E)-3-(5-chloro-2-hydroxyphenyl)acrylic acid
  参考文献：
  名称：

  钌催化选择性好氧氧化邻链烯基化取代酚与烯烃通过 CH 键活化

  摘要：

  在催化量的 [RuCl2(p-cymene)]2、AgSbF6 和 Cu(OAc)2·H2O 存在下，苯基氨基甲酸酯和乙酸酯与烯烃的氧化偶联在空气中提供了高度区域和立体选择性方式。催化反应与各种烯烃相容，如丙烯酸酯、乙烯基砜、丙烯腈和取代苯乙烯。本催化反应还与芳香环上具有各种富电子、缺电子和卤素取代基的氨基甲酸苯酯和乙酸酯相容。用取代的乙酸苯酯进一步检查催化反应。以LiOH·H2O或K2CO3为碱，取代的烯烃衍生物转化为相应的苯酚衍生物。为了说明催化反应，

  DOI：

  10.1002/ejoc.201201463

文献信息

• Design, synthesis and biological evaluation of novel trimethylpyrazine-2-carbonyloxy-cinnamic acids as potent cardiovascular agents
  作者：Hongfei Chen、Guoning Li、Peng Zhan、Hong Li、Shouxun Wang、Xinyong Liu

  DOI：10.1039/c4md00022f

  日期：——

  A series of novel trimethylpyrazine-2-carbonyloxy-cinnamic acids and esters were designed, synthesized and evaluated for their inhibitory effect on adenosine diphosphate (ADP)-induced platelet aggregation in vitro and also assayed for their protective effect against hydrogen peroxide (H2O2)-induced oxidative damage on Ea.hy926 cells. The results showed that many compounds exhibited high activity in one or both of the assays, of which, compound F′10 displayed the highest protective effect on the proliferation of the damaged Ea.hy926 cells (EC50 = 1.7 μM), presenting almost 40 times higher potency than that of lipoic acid, and compound F3 was the most active anti-platelet aggregation agent with IC50 = 9.6 μM, comparable to that of clopidogrel. The structure–activity relationships of these compounds were also discussed.

  研究人员设计、合成了一系列新型三甲基吡嗪-2-甲酰氧基肉桂酸及其酯类化合物，并评估了它们对体外二磷酸腺苷（ADP）诱导的血小板聚集的抑制作用，同时还检测了它们对过氧化氢（H2O2）诱导的 Ea.hy926 细胞氧化损伤的保护作用。结果表明，许多化合物在一种或两种试验中都表现出较高的活性，其中化合物 F′10 对受损 Ea.hy926 细胞的增殖具有最高的保护作用（EC50 = 1.7 μM），其效力比硫辛酸高近 40 倍；化合物 F3 是最活跃的抗血小板聚集剂，其 IC50 = 9.6 μM，与氯吡格雷相当。此外，还讨论了这些化合物的结构-活性关系。
• Dey; Row, Journal of the Chemical Society, 1924, vol. 125, p. 561
  作者：Dey、Row

  DOI：——

  日期：——
• Herniation through both Winslow’s foramen and a lesser omental defect: Report of a case
  作者：Yoshihisa Saida、Jiro Nagao、Makoto Takase、Yasumitsu Noto、Shinya Kusachi、Yoshihiro Kajiwara、Yoshinobu Sumiyama

  DOI：10.1007/s005950070125

  日期：2000.6

  The herniation of small bowel through Winslow's foramen is a rare type of internal hernia which ran cause ileus; however, a hernia traversing the lesser sac is even more unusual. To the best of our knowledge, only 25 cases of herniation through Winslow's foramen and 10 cases of lesser sac hernia have been reported in the Japanese literature. We describe herein the case of a 33-year-old man who presented to our hospital complaining of abdominal pain in whom a plain abdominal radiograph revealed small bowel gas with air-fluid levels, suggesting ileus. Following admission, an ileus tube was inserted, but the intestinal shadow did not improve and surgery was performed based on suspicion of an internal hernia. Approximately 100 cm of ileum was found to have herniated through a defect in the lesser omentum after passing through Winslow's foramen, Since the herniated bowel was viable, manual reduction without resection was performed. The patient had a satisfactory postoperative course, and was discharged on postoperative day 11, There are many unknown aspects surrounding the etiology of Winslow's foramen hernia and lesser sac hernia, and although internal hernia is a rare cause of ileus, its possibility should be kept in mind.
• Baesecke, Justus Liebigs Annalen der Chemie, 1870, vol. 154, p. 85
  作者：Baesecke

  DOI：——

  日期：——
• Copper/Silver-Mediated Cascade Reactions for the Construction of 2-Sulfonylbenzo[<i>b</i>]furans from <i>trans</i>-2-Hydroxycinnamic Acids and Sodium Sulfinates
  作者：Hong-Shuang Li、Gang Liu

  DOI：10.1021/jo4024478

  日期：2014.1.17

  Efficient construction of 2-sulfonylbenzo[b]furans is achieved from readily available trans-2-hydroxycinnamic acids and sodium sulfinates mediated by the CuCl2 center dot 2H(2)O/AgTFA system under mild conditions. This unprecedented synthetic protocol provides expedient access to a series of products in one step via a protodecarboxylation/C-S bond formation/C-O bond formation cascade.