3-phenyl-2-(2-thienyl)acrylic acid | 38313-33-6

• 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
• 英文名称: 3-phenyl-2-(2-thienyl)acrylic acid
• 英文别名: 3-phenyl-2-thien-2-ylpropenoic acid；(2E)-3-phenyl-2-thien-2-ylacrylic acid；(E)-3-phenyl-2-thiophen-2-ylprop-2-enoic acid
• CAS: 38313-33-6
• 化学式: C₁₃H₁₀O₂S
• 分子量: 230.287
• InChiKey: PRFYTLRQUHFIRX-LUAWRHEFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  16
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  65.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (+)-6-aminopenicilanic acid 、 草酰氯 、 3-phenyl-2-(2-thienyl)acrylic acid 在 sodium methylate 、 sodium carbonate 作用下， 以 N-甲基乙酰胺 、 甲醇 、 水 、 丙酮 、 苯 为溶剂， 生成 (2S-顺式)-3,3-二甲基-7-氧代-4-硫杂-1-氮杂双环[3.2.0]庚烷-2-羧酸
  参考文献：
  名称：

  Cephalosporin derivatives

  摘要：

  这是一种新型抗生素化合物，为7-β-丙烯酰胺基头孢-3-烯-4-羧酸和6-β-丙烯酰胺基青霉烷-3-羧酸及其非毒性衍生物。其中丙烯酰胺基具有结构式##STR1##其中A为芳基，B为取代或未取代的低烷基、低烯基或低炔基；或为芳基、环烷基或环烯基。这些化合物具有对革兰氏阳性和革兰氏阴性细菌的抗菌活性，并具有对β-内酰胺酶的稳定性。本发明还涉及该化合物的给药方法。

  公开号：

  US04014869A1
• 作为产物：
  描述：

  2-噻吩乙酸 、 苯甲醛 在 乙酸酐 、 三乙胺 作用下， 反应 1.0h， 生成 3-phenyl-2-(2-thienyl)acrylic acid 、 3-phenyl-2-(2-thienyl)acrylic acid
  参考文献：
  名称：

  CH⋯S hydrogen bonds as the organising force in 2,3-thienyl- and phenyl- or 2,3-dithienyl-substituted propenoic acid aggregates studied by the combination of FT-IR spectroscopy and computations

  摘要：

  Various propenoic acid stereoisomers 2,3-disubstituted with thienyl and/or phenyl groups were synthesised and their aggregation behaviour was studied both in solution and in the solid state by experimental (mid-range FT-IR spectroscopy) and computational (semiempirical and ab initio) methods. Experimental approach embraced the identification of potential hydrogen bonding sites through finding the relevant IR bands and monitoring their displacement upon increasing the acid concentration in solution and on going from solution to the solid state. In solution O-H center dot center dot center dot O hydrogen bonds were only found providing short-range ordering, while in the solid state C-H center dot center dot center dot S hydrogen bonds were identified. Hydrogen bonding sites could be assigned and relevant aggregate models could be built. Molecular modelling allowed obtaining good estimates for hydrogen bond lengths and angles and visualisation of the geometric arrangements. (C) 2010 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.molstruc.2010.09.033

文献信息

• Karminski-Zamola, G.; Bajic, M., Synthetic Communications, 1989, vol. 19, # 7,8, p. 1325 - 1334
  作者：Karminski-Zamola, G.、Bajic, M.

  DOI：——

  日期：——
• LCOVA, M.;HRNCIAR, P., CHEM. ZVESTI, 1985, 39, N 1, 135-142
  作者：LCOVA, M.、HRNCIAR, P.

  DOI：——

  日期：——
• CH⋯S hydrogen bonds as the organising force in 2,3-thienyl- and phenyl- or 2,3-dithienyl-substituted propenoic acid aggregates studied by the combination of FT-IR spectroscopy and computations
  作者：K. Csankó、L. Illés、K. Felföldi、J.T. Kiss、P. Sipos、I. Pálinkó

  DOI：10.1016/j.molstruc.2010.09.033

  日期：2011.5

  Various propenoic acid stereoisomers 2,3-disubstituted with thienyl and/or phenyl groups were synthesised and their aggregation behaviour was studied both in solution and in the solid state by experimental (mid-range FT-IR spectroscopy) and computational (semiempirical and ab initio) methods. Experimental approach embraced the identification of potential hydrogen bonding sites through finding the relevant IR bands and monitoring their displacement upon increasing the acid concentration in solution and on going from solution to the solid state. In solution O-H center dot center dot center dot O hydrogen bonds were only found providing short-range ordering, while in the solid state C-H center dot center dot center dot S hydrogen bonds were identified. Hydrogen bonding sites could be assigned and relevant aggregate models could be built. Molecular modelling allowed obtaining good estimates for hydrogen bond lengths and angles and visualisation of the geometric arrangements. (C) 2010 Elsevier B.V. All rights reserved.
• Cephalosporin derivatives
  申请人：Glaxo Laboratories Limited

  公开号：US04014869A1

  公开（公告）日：1977-03-29

  Novel antibiotic compounds which are 7.beta.-acrylamidoceph-3-em-4-carboxylic acids, and 6.beta.-acrylamidopenam-3-carboxylic acids and non-toxic derivatives thereof wherein the acrylamido group has the structure ##STR1## wherein A is aryl group and B is a substituted or unsubstituted lower alkyl, lower alkenyl or lower alkynyl group; or an aryl, cycloalkyl or cycloalkenyl group. These compounds possess antibacterial activity against gram-positive and gram-negative organisms coupled with stability to .beta.-lactamases. The invention further relates to the administration of the compounds.

  这是一种新型抗生素化合物，为7-β-丙烯酰胺基头孢-3-烯-4-羧酸和6-β-丙烯酰胺基青霉烷-3-羧酸及其非毒性衍生物。其中丙烯酰胺基具有结构式##STR1##其中A为芳基，B为取代或未取代的低烷基、低烯基或低炔基；或为芳基、环烷基或环烯基。这些化合物具有对革兰氏阳性和革兰氏阴性细菌的抗菌活性，并具有对β-内酰胺酶的稳定性。本发明还涉及该化合物的给药方法。