2-phenylethyl hydrogen maleate | 79923-11-8

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: 2-phenylethyl hydrogen maleate
• 英文别名: (Z)-4-oxo-4-(phenethyloxy)-2-butenoic acid；(Z)-4-oxo-4-(2-phenylethoxy)but-2-enoic acid
• CAS: 79923-11-8
• 化学式: C₁₂H₁₂O₄
• 分子量: 220.225
• InChiKey: XTPLWVHXBVTIOB-SREVYHEPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  16
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  63.6
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2-phenylethyl hydrogen maleate 在 氯化亚砜 作用下， 以 甲苯 为溶剂， 反应 2.0h， 生成 Fumarsaeuremono(2-phenyl)ethylesterchlorid
  参考文献：
  名称：

  Irreversible blockage of opioid receptor types by ester homologs of .beta.-funaltrexamine

  摘要：

  A series of ester homologues 2-5 of the mu receptor nonequilibrium antagonist beta-funaltrexamine (1, beta-FNA) was synthesized. These ligands were of interest in our investigation of the relationship between the structure of the ester function and the ability to irreversibly block mu opioid receptors. While all of the ligands were potent reversible agonists in the guinea pig ileum (GPI) and mouse vas deferens (MVD) preparations, most appeared to behave as irreversible antagonists of morphine. The benzyl 5 and phenethyl 6 esters possessed irreversible mu antagonist potency that was of similar magnitude to that of beta-FNA in the GPI. In the MVD, all esters appeared to irreversibly block the agonist effect of morphine, but none of the compounds irreversibly antagonized [D-Ala2,D-Leu5]enkephalin to a significant degree. [3H]Dihydromorphine displacement studies revealed no relationship between the affinity of the esters 1-6 and the irreversible blockage of mu receptors in the GPI or MVD. Possible reasons for the observed structure-activity relationship are discussed.

  DOI：

  10.1021/jm00160a013
• 作为产物：
  描述：

  马来酸酐 、 苯乙醇 在 三乙胺 作用下， 反应 1.0h， 生成 2-phenylethyl hydrogen maleate
  参考文献：
  名称：

  Irreversible blockage of opioid receptor types by ester homologs of .beta.-funaltrexamine

  摘要：

  A series of ester homologues 2-5 of the mu receptor nonequilibrium antagonist beta-funaltrexamine (1, beta-FNA) was synthesized. These ligands were of interest in our investigation of the relationship between the structure of the ester function and the ability to irreversibly block mu opioid receptors. While all of the ligands were potent reversible agonists in the guinea pig ileum (GPI) and mouse vas deferens (MVD) preparations, most appeared to behave as irreversible antagonists of morphine. The benzyl 5 and phenethyl 6 esters possessed irreversible mu antagonist potency that was of similar magnitude to that of beta-FNA in the GPI. In the MVD, all esters appeared to irreversibly block the agonist effect of morphine, but none of the compounds irreversibly antagonized [D-Ala2,D-Leu5]enkephalin to a significant degree. [3H]Dihydromorphine displacement studies revealed no relationship between the affinity of the esters 1-6 and the irreversible blockage of mu receptors in the GPI or MVD. Possible reasons for the observed structure-activity relationship are discussed.

  DOI：

  10.1021/jm00160a013

文献信息

• Zn(ClO4)2·6H2O as a Powerful Catalyst for a Practical Acylation of Alcohols with Acid Anhydrides
  作者：Giuseppe Bartoli、Marcella Bosco、Renato Dalpozzo、Enrico Marcantoni、Massimo Massaccesi、Letizia Sambri

  DOI：10.1002/ejoc.200300458

  日期：2003.12

  new protocol for the acylation of alcohols with anhydrides in the presence of Zn(ClO4)2·6H2O as the catalyst is reported. The activity of Zn(ClO4)2·6H2O has been proven to be superior to that exerted by dry Mg(ClO4)2 and by metal triflates. Its efficiency allows reactions between poorly reactive substrates, such as sterically hindered tertiary alcohols and aromatic anhydrides. All of the reactions

  报道了一种在 Zn(ClO4)2·6H2O 作为催化剂的情况下用酸酐酰化醇的新方案。已证明 Zn(ClO4)2·6H2O 的活性优于干燥的 Mg(ClO4)2 和金属三氟甲磺酸盐。其效率允许反应性较差的底物（例如位阻叔醇和芳香酸酐）之间发生反应。所有反应均以1:1.05的醇/酸酐比进行。从实用和经济的角度来看，这些条件非常方便，因为它们避免了试剂的浪费并允许简单的后处理程序。Zn(ClO4)2·6H2O 的催化作用对酸酐的活化非常特殊，以至于在酯化过程中对酸敏感的官能团和起始材料的立体化学构型保持不变。在所有情况下，酰化产物都是以纯形式定量获得的。(© Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2003)
• Controlled Release of Perfumery Alcohols by Neighboring-Group Participation. Comparison of the Rate Constants for the Alkaline Hydrolysis of 2-Acyl-, 2-(Hydroxymethyl)-, and 2-Carbamoylbenzoates
  作者：Jean-Yves de Saint Laumer、Eric Frérot、Andreas Herrmann

  DOI：10.1002/hlca.200390236

  日期：2003.8

  2-[(ethylamino)carbonyl]benzoates were found to have the highest rate constants for the alkaline ester hydrolysis, followed by unsubstituted 2-(aminocarbonyl)benzoates, or the corresponding isopropyl derivatives. To rationalize the influence of the different structural changes on the hydrolysis kinetics, the experimental data obtained for the 2-[(alkylamino)carbonyl]benzoates were compared with the

  一系列的2- acylbenzoates 1和2，2-（羟甲基）苯甲酸酯3，2-carbamoylbenzoates 4 - 6，以及氨基甲酰酯7或8分别的马来酸盐或琥珀酸盐，（参见图2），在制备几个反应步骤，并研究了这些化合物作为伯，仲和叔香料醇的受控释放的化学传递系统的潜在用途。通过肛门确定邻基团辅助的碱性酯水解的速率常数。在不同pH的H 2 O / MeCN缓冲溶液中进行HPLC （表1）。发现水解速率取决于醇的结构，前体骨架以及攻击酯功能的相邻亲核试剂的结构。伯醇的释放速度比仲醇和叔醇要快，而烯丙基伯醇（例如香叶醇）的苯甲酸酯的水解速度比同源饱和醇（如香茅醇）快2-4倍。对于相同的离去醇，环2-[（（乙基氨基）羰基]苯甲酸酯的环化速度比相应的2-（羟甲基）苯甲酸酯快，并且环化的速度比其2-甲酰基和2-乙酰基类似物快（例如，参见图4。）。在氨基甲酸酯系列中，发现2-[（（乙基氨基）羰
• Hydroxyl group graft modified polyolefins
  申请人：GENERAL ELECTRIC COMPANY

  公开号：EP0186060A2

  公开（公告）日：1986-07-02

  57 Polyolefins are graft modified with functional hydroxyl groups through an imide linkage and chemically reacted with polymerized polycarbonates, polyesters, and/or poly(ester- carbonates) to produce a thermoplastic molding composition.

  57 聚烯烃通过酰亚胺连接与功能性羟基接枝改性，并与聚合的聚碳酸酯、聚酯和/或聚（酯-碳酸酯）发生化学反应，生成热塑性成型组合物。
• Structure–activity relationships of trans-substituted-propenoic acid derivatives on the nicotinic acid receptor HCA2 (GPR109A)
  作者：J.P.D. van Veldhoven、C.C. Blad、C.M. Artsen、C. Klopman、D.R. Wolfram、M.J. Abdelkadir、J.R. Lane、J. Brussee、A.P. IJzerman

  DOI：10.1016/j.bmcl.2010.11.091

  日期：2011.5

  Nicotinic acid (niacin) has been used for decades as an antidyslipidemic drug in man. Its main target is the hydroxy-carboxylic acid receptor HCA2 (GPR109A), a G protein-coupled receptor. Other acids and esters such as methyl fumarate also interact with the receptor, which constituted the basis for the current study. We synthesized a novel series of substituted propenoic acids, such as fumaric acid esters, fumaric acid amides and cinnamic acid derivatives, and determined their affinities for the HCA2 receptor. We observed a rather restricted binding pocket on the receptor with trans-cinnamic acid being the largest planar ligand in our series with appreciable affinity for the receptor. Molecular modeling and analysis of the structure-activity relationships in the series suggest a planar trans-propenoic acid pharmacophore with a maximum length of 8 angstrom and out-of-plane orientation of the larger substituents. (C) 2010 Elsevier Ltd. All rights reserved.
• GRAFT COPOLYMERS OF POLYFARNESENES WITH CONDENSATION POLYMERS
  申请人：Amyris, Inc.

  公开号：EP2601229A1

  公开（公告）日：2013-06-12