ethyl (E)-2-acetyl-3-oxo-5-phenylpent-4-enoate | 76352-65-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: ethyl (E)-2-acetyl-3-oxo-5-phenylpent-4-enoate
• 英文别名: (E)-2-cinnamoylacetoacetic ethyl ester；2-trans-cinnamoyl-acetoacetic acid ethyl ester；2-trans-Cinnamoyl-acetessigsaeure-aethylester；(+/-)-2-trans-Cinnamoyl-acetessigsaeure-ethylester
• CAS: 76352-65-3
• 化学式: C₁₅H₁₆O₄
• 分子量: 260.29
• InChiKey: OABDLSWGEMVREJ-MDZDMXLPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  19
• 可旋转键数：
  7
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  60.4
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  ethyl (E)-2-acetyl-3-oxo-5-phenylpent-4-enoate 在 乙醇 、 钯 作用下， 生成 2-acetyl-3-oxo-5-phenyl-valeric acid ethyl ester
  参考文献：
  名称：

  Borsche; Lewinsohn, Chemische Berichte, 1933, vol. 66, p. 1792,1796

  摘要：

  DOI：
• 作为产物：
  描述：

  3-oxo-2-trans-cinnamoyl-glutaric acid-1-ethyl ester 生成 ethyl (E)-2-acetyl-3-oxo-5-phenylpent-4-enoate
  参考文献：
  名称：

  Le bloc du nerf sciatique réalisé avec de la bupivacaïne encapsulée dans des microsphères prévient l’hyperalgésie dans un modèle inflammatoire animal

  摘要：

  Purpose: The aim of this study was to evaluate the effect of different durations of local anesthetic neural blockade on hyperalgesia after carrageenan infiltration in a rat model,Methods: Inflammation was obtained by injection of carrageenan in the righ hind paw. Hyperalgesia was determined by measuring the threshold of response to increasing mechanical stimuli on the contralateral and on the ipsilateral paw. The development of edema was measured. After identification of the sciatic nerve by nerve stimulation, blockade was performed either one hour before or after carrageenan infiltration. Animals were randomly assigned into three groups: without sciatic nerve block (control group; n = 20), block with bupivacaine (B) and block with bupivacaine-loaded microspheres (B-Ms) injection before or after carrageenan infiltration (n = 10 for each group).Results: Carrageenan infiltration in the control group induced a severe ipsilateral and contralateral hyperalgesia. After blockade with B (duration = 2 +/- 0.5 hr) hyperalgesia was present and delayed only by the duration of the local anesthetic effect. A longer duration of block achieved with B-Ms (duration greater than five hours), was associated with the absence of development of both ipsilateral and contralateral hyperalgesia. No preemptive effect was recorded.Conclusion: B-Ms as a drug delivery system prolongs the duration of neural blockade and avoids hyperalgesia phenomena in this rat model of inflammation.

  DOI：

  10.1007/bf03017447

文献信息

• 5-Cinnamoyl- and 5-(Ethoxycarbonyl)-6-styryl Derivatives of 4-Aryl-3,4-dihydropyrimidin-2(1H)-ones
  作者：Maksim A. Kolosov、Valeriy D. Orlov、Valeriy V. Vashchenko、Svetlana V. Shishkina、Oleg V. Shishkin

  DOI：10.1135/cccc20071219

  日期：——

  Several 5-cinnamoyl- and 5-(ethoxycarbonyl)-6-styryl derivatives of 4-aryl-3,4-dihydropyrimidin-2(1H)-ones were obtained and their physicochemical properties were investigated. The introduction of alkyl substituent in position 1 of dihydropyrimidine ring was shown to promote the Claisen-Schmidt reaction on acetyl group only; without the alkyl both acetyl and 6-methyl groups participate in the reaction.

  得到了几种4-芳基-3,4-二氢嘧啶-2(1H)-酮的5-肉桂酰基和5-(乙氧羰基)-6-苯乙烯基衍生物，并研究了它们的物理化学性质。在二氢嘧啶环的1位引入烷基取代基表明仅促进了乙酰基上的克莱森-施密特反应；没有烷基时，乙酰基和6-甲基基团都参与反应。
• Borsche; Lewinsohn, Chemische Berichte, 1933, vol. 66, p. 1792,1796
  作者：Borsche、Lewinsohn

  DOI：——

  日期：——
• Gandini, Gazzetta Chimica Italiana, 1943, vol. 73, p. 263,269
  作者：Gandini

  DOI：——

  日期：——
• Gandini, Gazzetta Chimica Italiana, 1948, vol. 78, p. 135,140
  作者：Gandini

  DOI：——

  日期：——
• β-Substituted Acryloylacetic Esters
  作者：James English、Leon J. Lapides

  DOI：10.1021/ja01252a503

  日期：1943.12