ethyl α-(hydroxymethyl)benzenepropanoate | 107749-65-5

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羟基酸及其衍生物
• 英文名称: ethyl α-(hydroxymethyl)benzenepropanoate
• 英文别名: ethyl 2-(hydroxymethyl)-3-phenylpropionate；Ethyl 2-benzyl-3-hydroxypropanoate
• CAS: 107749-65-5
• 化学式: C₁₂H₁₆O₃
• 分子量: 208.257
• InChiKey: OBMFDJXMVDATQK-UHFFFAOYSA-N

物化性质

• 沸点：
  335.8±22.0 °C(Predicted)
• 密度：
  1.098±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  15
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  46.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  ethyl α-(hydroxymethyl)benzenepropanoate 在 盐酸 、 酒石酸 、 氯化铵 作用下， 以 二氯甲烷 、 水 、 甲苯 为溶剂， 反应 1.5h， 生成 ethyl 2-formyl-3-phenylpropionate
  参考文献：
  名称：

  [1,2,4]THIADIAZINE 1,1-DIOXIDE COMPOUNDS

  摘要：

  这项发明涉及[1,2,4]噻二嗪1,1-二氧化物化合物和含有这种化合物的药物组合物，可用于治疗丙型肝炎病毒感染。

  公开号：

  US20090306057A1
• 作为产物：
  描述：

  3-苯丙酸乙酯 在 palladium on activated charcoal 氢气 、 lithium diisopropyl amide 作用下， 以 乙醇 为溶剂， -78.0 ℃ 、34.48 kPa 条件下， 反应 1.25h， 生成 ethyl α-(hydroxymethyl)benzenepropanoate
  参考文献：
  名称：

  Analogs of the .delta. opioid receptor selective cyclic peptide [cyclic][2-D-penicillamine,5-D-penicillamine]-enkephalin: 2',6'-dimethyltyrosine and Gly3-Phe4 amide bond isostere substitutions

  摘要：

  In order to develop systemically-active opioid peptides, the delta-selective, opioid pentapeptide [D-Pen2,D-Pen5]-enkephalin (DPDPE) was modified by esterification and by substitution of 2,6-dimethyltyrosine for tyrosine to yield 4. Compound 4 was on the order of 8- and 800-fold more active than DPDPE in both delta and mu-opioid radioligand binding assays, respectively, in rat neural membrane suspensions. Compound 4 was considerably more potent than DPDPE at inhibiting contractions of electrically-stimulated mouse vas deferens in vitro, and this effect was very sensitive to naltrindole, a delta-selective opioid antagonist. These observations can be taken as indication that 4 exerts its effects through delta-opioid receptors. This interpretation is supported by the finding that the EC50 value of 4 derived in the smooth muscle assay is very similar to that derived in NG108-15 neuroblastoma cells, a preparation devoid of mu-receptors. Unlike DPDPE, 4 exhibited significant, naloxone-sensitive, antinociceptive activity when administered systemically, as measured by inhibition of phenylbenzquinone-induced stretching in mice (ED50 = 2.1 mg/kg). Compound 4 also displayed significant antinociceptive activity following systemic administration as measured by its action in mice to increase latencies for tail withdrawal from radiant heat (ED50 = 50 mg/kg). Compound 4 did not produce morphine-like discriminative stimulus effects in rats trained to discriminate 3.0 mg/kg morphine from vehicle at doses ranging from 30 to 120 mg/kg. This observation can be interpreted as indication that within this dosage range there is an absence of morphine-like subjective effects. Physical dependence, however, could be induced in mice at higher doses of 4 under a progressively-graded, 4-day dose regimen. Congeners of 4 with amide bond surrogates for the Gly-Phe amide bond (oxymethylene, trans-double bond, and bismethylene isosteres) in the cyclic core of DPDPE were prepared in an attempt to increase the antinociceptive activity of 4. While some of the were active in the in vitro assays, they did not display significant antinociceptive activity following systemic administration. The preparation of all the compounds was accomplished by solution-phase methods. The which might underlie the biological and systemic activity of 4 are discussed.

  DOI：

  10.1021/jm00094a002

文献信息

• Process for producing optically active 3-hydroxypropionic ester derivative
  申请人：Taoka Naoaki

  公开号：US20060166342A1

  公开（公告）日：2006-07-27

  The present invention is to provide a process for simply producing an optically active 3-hydroxypropionic ester derivative useful as a medicament intermediate from an inexpensive material. More specifically, the present invention is directed to a process for producing an optically active 3-hydroxypropionic ester derivative comprising reacting an acetic ester derivative available at low cost with abase and a formic ester, thereby converting the acetic ester derivative into a 2-formylacetic ester derivative, and thereafter, stereospecifically reducing the formyl group of the derivative by use of an enzymatic source capable of stereoselectively reducing the formyl group of the derivative.

  本发明提供了一种简单制备光学活性的3-羟基丙酸酯衍生物，该衍生物可用作药物中间体，从廉价原料中制备。更具体地，本发明涉及一种制备光学活性的3-羟基丙酸酯衍生物的方法，包括将一种低成本的乙酸酯衍生物与碱和甲酸酯反应，从而将乙酸酯衍生物转化为2-甲酰乙酸酯衍生物，然后使用能够立体选择性还原该衍生物的酶源，立体特异性地还原衍生物的甲酰基。
• PROCESS FOR PRODUCING OPTICALLY ACTIVE 3-HYDROXYPROPIONIC ESTER DERIVATIVE
  申请人：TAOKA Naoaki

  公开号：US20100016627A1

  公开（公告）日：2010-01-21

  A 2-formylacetic ester derivative represented by the general formula (5) is provided: where R 4 represents an alkyl group having 2 to 6 carbon atoms; R 5 represents an alkyl group having 1 to 10 carbon atoms; and X represents H, Li, Na or K.

  提供一种由一般式(5)表示的2-甲酰基乙酸酯衍生物：其中R4代表具有2至6个碳原子的烷基；R5代表具有1至10个碳原子的烷基；X代表H、Li、Na或K。
• Process for producing propionic acid derivatives
  申请人：Ajinomoto Co., Inc.

  公开号：EP0906901A2

  公开（公告）日：1999-04-07

  A process for producing a 2-aralkyl-3-hydroxypropionic acid (or its ester) comprises the steps of: reacting a 3-hydroxy-2-methylene-3-arylpropionic acid ester (which may be easily obtained by the reaction of an arylaldehyde with an acrylic acid ester), with an acid anhydride to form a 2-aralkylidene-3-acyloxypropionic acid ester; subjecting the same to hydrolysis or alcoholysis; and reducing the resulting 2-aralkylidene-3-hydroxypropionic acid or its ester. Especially, the presence of a base in the reduction step greatly improves the yield thereof. By the use of this process, 2-aralkyl-3-hydroxypropionic acid (or its ester), which are important as intermediates in various industrial syntheses, may be produced safely and easily on an industrial scale.

  生产 2-烷基-3-羟基丙酸（或其酯）的工艺包括以下步骤 将 3-羟基-2-亚甲基-3-芳基丙酸酯（可通过芳基醛与丙烯酸酯的反应轻松获得）与酸酐反应，形成 2-芳基亚甲基-3-乙酰氧基丙酸酯； 将其水解或醇解；以及 还原生成的 2-亚烷基-3-羟基丙酸或其酯。特别是在还原步骤中加入碱，可大大提高产率。 通过使用这种工艺，可以安全、简便地在工业规模上生产作为各种工业合成中重要中间体的 2-亚烷基-3-羟基丙酸（或其酯）。
• Esters α-méthyléniques et α-hydroxyméthylés par addition d'organolithiens ou magnésiens sur l' α-(hydroxymethyl) acrylate d'éthyle et ses dérivés en présence de cuivre(I)
  作者：Hassen Amri、Monique Rambaud、Jean Villieras

  DOI：10.1016/s0022-328x(00)99740-7

  日期：1986.7
• EP1568679
  申请人：——

  公开号：——

  公开（公告）日：——