3-phenyl-2-hexenoic acid | 4362-01-0

• 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-hexenoic acid
• 英文别名: 3-Propyl-3-phenyl-acrylsaeure；3-phenyl-hex-2-enoic acid；3-Phenyl-hex-2-ensaeure；β-propyl-cinnamic acid；3-Phenylhex-2-enoic acid
• CAS: 4362-01-0
• 化学式: C₁₂H₁₄O₂
• 分子量: 190.242
• InChiKey: JUYSLKGFKJWMCH-UHFFFAOYSA-N

物化性质

• 熔点：
  94°C
• 沸点：
  265.75°C (rough estimate)
• 密度：
  1.0527 (rough estimate)

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  14
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  37.3
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  3-phenyl-2-hexenoic acid 在 硫酸 作用下， 生成 5-ethyl-4-phenyl-dihydro-furan-2-one
  参考文献：
  名称：

  Johnson; Kon, Journal of the Chemical Society, 1926, p. 2755

  摘要：

  DOI：
• 作为产物：
  描述：

  alkaline earth salt of/the/ methylsulfuric acid 在 苯 作用下， 生成 3-phenyl-2-hexenoic acid
  参考文献：
  名称：

  Stoermer; Grimm; Laage, Chemische Berichte, 1917, vol. 50, p. 973

  摘要：

  DOI：

文献信息

• Direct Enantioselective and Regioselective Alkylation of β,γ-Unsaturated Carboxylic Acids with Chiral Lithium Amides as Traceless Auxiliaries
  作者：Kai Yu、Bukeyan Miao、Wenqi Wang、Armen Zakarian

  DOI：10.1021/acs.orglett.9b00587

  日期：2019.3.15

  Efficient asymmetric alkylation of β,γ-unsaturated carboxylic acids without prior functionalization is enabled by chiral lithium amides. Enantioselectivity is imparted by a putative mixed lithium amide–enediolate aggregate that acts a traceless auxiliary formed in situ, allowing for a direct asymmetric alkylation and a simple recovery of the chiral reagent.

  β，γ-不饱和羧酸的有效不对称烷基化无需事先官能化就可以通过手性锂酰胺实现。对映选择性是由假定的酰胺基-烯二醇锂混合聚集体赋予的，该聚集体发挥就地形成的无痕助剂的作用，允许直接不对称烷基化和简单回收手性试剂。
• Direct Competitive Enzyme-Linked Immunosorbent Assay for the Determination of the Highly Polar Short-Chain Sulfophenyl Carboxylates
  作者：M.-Carmen Estévez、Roger Galve、Francisco Sánchez-Baeza、M.-Pilar Marco

  DOI：10.1021/ac0502910

  日期：2005.8.1

  A direct enzyme-linked immunosorbent assay for the detection of the short-chain sulfophenylcarboxylic acids (SPCs), the main metabolites of the linear alkylbenzenesulfonates, is reported. Six SPCs (2C3, 2C4, 3C4, 2C5, 3C5, 3C6), differing in the length of the alkyl chain (between C3 and C6) and in the position of the phenylsulfonic group versus the carboxylic group, have been synthesized. Antibodies have been raised against a mixture of the corresponding horseshoe crab hemocyanin conjugates prepared by coupling the carboxylic acid to the lysine amino acid residues. The immunoassay As115/3C4−HRP achieves an IC50 value of 23 nM (6.67 μg L-1) and a detection limit of 0.85 nM (0.24 μg L-1), using as standard analyte an equimolar mixture of the six SPCs. The immunoassay has found to work better in media with low or moderate ionic strength (4−30 mS cm-1). The decrease in the detectability produced by the potential formation of SPC salts with divalent cations such as Ca2+ can be prevented by lowering the pH of the assay medium below the pKa value of the SPC carboxylic group and using a buffer chelating with properties such as citrate buffer. The assay can be considered specific for short-chain SPCs since congeners with longer alkyl chains and other pollutants containing sulfonic groups in their structure do not interfere significantly in the assay. Preliminary experiments addressed to evaluate the potential application of this assay to environmental water samples demonstrate the usefulness of the assay.

  报道了一种直接酶联免疫吸附测定法，用于检测短链硫磺苯羧酸（SPCs），即线性烷基苯磺酸的主要代谢产物。合成了六种SPCs（2C3、2C4、3C4、2C5、3C5、3C6），它们在烷基链的长度（在C3到C6之间）和苯磺酸根与羧酸根的相对位置上有所不同。针对将羧酸与赖氨酸氨基酸残基偶联所制备的相应马蹄蟹血蓝蛋白结合物的混合物，产生了抗体。免疫测定法As115/3C4−HRP的IC50值为23 nM（6.67 μg L-1），检测限为0.85 nM（0.24 μg L-1），标准分析物为六种SPCs的等摩尔混合物。研究发现，该免疫测定法在低或中等离子强度（4−30 mS cm-1）的介质中效果更佳。通过将测定介质的pH调至低于SPC羧酸根的pKa值，并使用具有螯合特性的缓冲液（如柠檬酸盐缓冲液），可以防止与二价阳离子（如Ca2+）形成SPC盐所导致的可检测性下降。该测定法可以认为是特异性针对短链SPCs，因为烷基链较长的同类物质及其结构中含有磺酸根的其他污染物在检测中不会显著干扰。初步实验评估了该测定法在环境水样中潜在应用的有效性，展示了该测定法的实用性。
• [EN] 1,3,4-ALKENYL OXADIAZOLE AMINO ACID DERIVATIVES AS SPHINGOSINE-1-PHOSPHATE RECEPTORS' MODULATORS<br/>[FR] DÉRIVÉS D'AMINOACIDE DE 1,3,4-ALCÉNYLE OXADIAZOLE EN TANT QUE MODULATEURS DES RÉCEPTEURS DE LA SPHINGOSINE-1-PHOSPHATE
  申请人：ALLERGAN INC

  公开号：WO2015073140A1

  公开（公告）日：2015-05-21

  The present invention relates to 1,3,4-alkenyl oxadiazole amino acid derivatives of formulae I and II, processes for preparing them, pharmaceutical compositions containing them and their use as pharmaceuticals as modulators of sphingosine-1-phosphate receptors.

  本发明涉及式I和式II的1,3,4-烯基氧代二唑氨基酸衍生物，其制备过程，含有它们的制药组合物以及它们作为调节鞘氨醇-1-磷酸受体的药物使用。
• BICYCLIC 1,3,4-OXADIAZOLE DERIVATIVES AS SPHINGOSINE-1-PHOSPHATE RECEPTORS' MODULATORS
  申请人：Allergan, Inc.

  公开号：US20160137616A1

  公开（公告）日：2016-05-19

  The present invention relates to bicyclic 1,3,4-oxadiazole derivatives, processes for preparing them, pharmaceutical compositions containing them and their use as pharmaceuticals as modulators of sphingosine-1-phosphate receptors.

  本发明涉及双环1,3,4-噁二唑衍生物，其制备过程，含有它们的制药组合物以及它们作为调节鞘氨醇-1-磷酸受体的药物的用途。
• Schroeter, Chemische Berichte, 1908, vol. 41, p. 11
  作者：Schroeter

  DOI：——

  日期：——