2-苄基-3-羟基丙酸甲酯 | 85677-12-9

• 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
• 中文名称: 2-苄基-3-羟基丙酸甲酯
• 英文名称: 2-benzyl-3-hydroxypropionic acid methyl ester
• 英文别名: 2-(hydroxymethyl)-3-phenylpropanoic acid methyl ester；2-benzyl-3-hydroxypropanoic acid methyl ester；methyl 3-hydroxy-2-benzylpropionate；methyl 2-benzyl-3-hydroxypropionate；α-hydroxymethylbenzenepropanoic acid methyl ester；Methyl 2-benzyl-3-hydroxypropanoate
• CAS: 85677-12-9
• 化学式: C₁₁H₁₄O₃
• mdl: MFCD11857764
• 分子量: 194.23
• InChiKey: NOULZVWNYXNCDH-UHFFFAOYSA-N

物化性质

• 沸点：
  321.7±22.0 °C(Predicted)
• 密度：
  1.121±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  14
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.363
• 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：

  2-苄基-3-羟基丙酸甲酯 在 盐酸 作用下， 以 甲醇 为溶剂， 生成 2-benzyl-3-hydroxypropanoic acid
  参考文献：
  名称：

  Process for producing propionic acid derivatives

  摘要：

  生产2-芳基-3-羟基丙酸（或其酯）的方法，包括以下步骤：将通过芳基醛与丙烯酸酯反应获得的3-羟基-2-亚甲基-3-芳基丙酸酯与酸酐反应，形成2-芳基亚甲基-3-酰氧基丙酸酯；将其进行水解或醇解；并还原所得的2-芳基亚甲基-3-羟基丙酸或其酯。还原步骤可在碱的存在下进行。

  公开号：

  US06242635B1
• 作为产物：
  描述：

  2-(乙酰氧基甲基)-3-苯基-丙酸 在 甲醇 、 水 、 potassium carbonate 、 乙酰氯 作用下， 反应 26.0h， 生成 2-苄基-3-羟基丙酸甲酯
  参考文献：
  名称：

  Cleavage of β-lactone ring by serine protease. Mechanistic implications

  摘要：

  Both enantiomers of 3-benzyl-2-oxctanone (1) were found to be slowly hydrolyzed substrates of a-chymotrypsin having k(cat) values of 0.134 +/- 0.008 and 0.105 +/- 0.004min(-1) for (R)-1 and (S)-1, respectively, revealing that alpha-CT is virtually unable to differentiate the enantiomers in the hydrolysis of 1. The initial step to form the acyl-enzyme intermediate by the attack of Ser-195 hydroxyl on the beta-lactone ring at the 2-position in the hydrolysis reaction may not be enzymatically driven, but the relief of high ring strain energy of beta-lactone may constitute a major driving force. The deacylation step is also attenuated, which is possibly due to the hydrogen bond that would be formed between the imidazole nitrogen of His-57 and the hydroxyl group generated during the acylation in the case of (R)-1, but in the alpha-CT catalyzed hydrolysis of (S)-1 the imidazole nitrogen may form a hydrogen bond with the ester carbonyl oxygen. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0968-0896(02)00108-6

文献信息

• Hydroformylation of olefins with paraformaldehyde catalyzed by rhodium complexes
  作者：Tamon Okano、Teruyuki Kobayashi、Hisatoshi Konishi、Jitsuo Kiji

  DOI：10.1016/s0040-4039(00)85762-7

  日期：1982.1

  The addition of formaldehyde to olefins is efficiently catalyzed by RhH2(O2COH)[P(i-Pr)3]2 and gives the corresponding aldehydes in neutral solution.

  RhH 2（O 2 COH）[P（i-Pr）3 ] 2有效催化甲醛加到烯烃中，并在中性溶液中得到相应的醛。
• Xanthines with C8 chiral substituents as potent and selective adenosine A1 antagonists
  作者：Norton P. Peet、Nelsen L. Lentz、Mark W. Dudley、Ann Marie L. Ogden、Deborah R. McCarty、Margaret M. Racke

  DOI：10.1021/jm00077a004

  日期：1993.12

  Several 8-substituted 1,3-dipropylxanthines were synthesized, and their receptor binding affinities at adenosine A1 and A2 receptors were measured. When enantiomeric pairs of compounds were examined, the R enantiomers were significantly more potent than the corresponding S enantiomers. The most potent compound at the A1 receptor was (R)-3,7-dihydro-8-(1-methyl-2-phenylethyl)-1,3-dipropyl-1H-purine-2,6-di

  合成了几种8-取代的1,3-二丙基黄嘌呤，并测量了它们在腺苷A1和A2受体上的受体结合亲和力。当检查化合物的对映异构体对时，R对映异构体比相应的S对映异构体显着更有效。在A1受体上最有效的化合物是（R）-3,7-二氢-8-（1-甲基-2-苯乙基）-1,3-二丙基-1H-嘌呤-2,6-di one（5a; MDL 102,503），其在A1受体处的Ki值为6.9 nM。但是，更具选择性的化合物是（R）-3,7-二氢-8-（1-苯丙基）-1,3-二丙基-1H-嘌呤-2,6-二酮（5d； MDL 102,234）， A1受体的Ki值为23.2 nM，A2 / A1的比率为153。
• Asymmetric Synthesis of the Roche Ester and its Derivatives by Rhodium‐INDOLPHOS‐Catalyzed Hydrogenation
  作者：Jeroen Wassenaar、Mark Kuil、Joost N. H. Reek

  DOI：10.1002/adsc.200800209

  日期：2008.7.7

  lpropionate, known as the Roche ester, and several of its derivatives were successfully synthesized through asymmetric rhodium-catalyzed hydrogenation, using INDOLPHOS (diisopropyl1-[(S)-3,5-dioxa-4-phosphacyclohepta[2,1-a;3,4-a′]dinaphthalen-4-yl]-3-methyl-2-indolyl}phosphine) as the chiral ligand, in excellent yield and the highest ee reported up to now (TOF over 5500 h−1 at 25 °C; up to 98% ee

  （S）-3-羟基-2-甲基丙酸酯（称为Roche酯）及其一些衍生物是使用INDOLPHOS（二异丙基1-[（S）-3,5- dioxa）通过不对称铑催化的氢化反应成功合成的作为手性配体的-4-膦酰基环庚[[2,1- a ; 3,4- a' ]二萘基-4-基] -3-甲基-2-吲哚基}膦）具有优异的收率，据报道，最高ee现在（25°C下5500 h -1下的TOF ；-40°C下ee高达98％）。
• Highly regioselective intramolecular hydroxymethylation of α,β-unsaturated carboxylic acids
  作者：Torsten Linker、Michael Maurer、Frank Rebien

  DOI：10.1016/0040-4039(96)01931-4

  日期：1996.11

  A convenient synthesis of hydroxy esters 7 and lactones 8 by starting from easily available α,β-unsaturated carbocyclic acids 4 is described. The key step of this transformation is a hitherto unknown radical cyclization of silyl esters, which exhibits a high degree of regioselectivity through steric and orbital control.

  描述了通过从容易获得的α，β-不饱和碳环酸4开始方便地合成羟基酯7和内酯8的方法。该转变的关键步骤是迄今为止尚未发现的甲硅烷基酯的自由基环化反应，该反应通过空间和轨道控制显示出很高的区域选择性。
• Selective adenosine receptor agents
  申请人：Merrell Dow Pharmaceuticals Inc.

  公开号：US05047534A1

  公开（公告）日：1991-09-10

  Xanthine derivative which act selectively at adenosine receptors and which act in general as adenosine antagonists are disclosed. From in vitro studies it is known that specific physiological effects can be distinguished as a result of this selectively and that adenosine receptor activity in vitro correlates with adenosine receptor activity in vivo. Pharmaceutical preparations of the subject compounds can be prepared on the basis of the selective binding activity of the compounds disclosed herein which will enhance certain physiological effects while minimizing others, such as decreasing blood pressure without decreasing heart rate.

  本发明揭示了一种在腺苷受体上选择性作用以及通常作为腺苷拮抗剂的黄嘌呤衍生物。从体外研究中已知，由于这种选择性，可以区分出特定的生理效应，并且体外腺苷受体活性与体内腺苷受体活性相关。基于本文所述化合物的选择性结合活性，可以制备该主题化合物的制药制剂，从而增强某些生理效应，同时最小化其他效应，例如降低血压而不降低心率。