(S)-2-苯氧基丙酸甲酯 | 115880-48-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 中文名称: (S)-2-苯氧基丙酸甲酯
• 英文名称: S-2-phenoxypropionic acidmethyl ester
• 英文别名: (S)-methyl 2-phenoxypropanoate；(S)-methyl 2-phenoxypropionate；(s)-2-Phenoxypropionic acid methyl ester；methyl (2S)-2-phenoxypropanoate
• CAS: 115880-48-3
• 化学式: C₁₀H₁₂O₃
• 分子量: 180.203
• InChiKey: KIBRBMKSBVQDMK-QMMMGPOBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  13
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  35.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (S)-2-苯氧基丙酸甲酯 、 溴乙酰溴 在 三氯化铝 作用下， 以 二氯甲烷 为溶剂， 反应 6.0h， 以84%的产率得到(S)-methyl 2-[4-(2-bromoacetyl)phenoxy]-propanoate
  参考文献：
  名称：

  立体特异合成和新型β（3）-肾上腺素受体激动剂和反向激动剂的生物活性。

  摘要：

  由于β（3）-肾上腺素能受体广泛分布于体内，因此正成为治疗多种疾病的诱人靶标，例如肥胖，2型糖尿病，代谢综合征，恶病质，膀胱过度活动症，肠道溃疡性炎症，早产，焦虑和抑郁症以及心力衰竭。以高收率制备属于具有一个或两个立体生成中心的芳基乙醇胺类的新化合物，为外消旋体和旋光形式。然后，评估他们对β（3）-肾上腺素受体的内在活性以及对β（1）-和β（2）-肾上腺素受体的亲和力。发现立体化学特征在确定此类化合物的行为中起关键作用。特别是，α-外消旋，（alphaR）-和（alphaS）-2- {4- [2-（2-（2-羟基-2-苯基乙基氨基）乙基]苯氧基} -2-甲基丙酸，（alpha-rac，beta-rac）-，（alphaR，发现βS）-和（αR，βR）-2- {4- [2-（2-（2-羟基-2-苯基乙基氨基）乙基]苯氧基}丙酸具有β（3）-肾上腺素受体激动活性。而（alphaS，betaS）-和（alphaS，betaR）-2-

  DOI：

  10.1016/j.bmc.2007.11.060
• 作为产物：
  描述：

  2-苯氧基丙酸 在 对甲苯磺酸 、 2,2-二甲氧基丙烷 作用下， 反应 4.0h， 生成 (S)-2-苯氧基丙酸甲酯
  参考文献：
  名称：

  Chenevert, Robert; D'Astous, Linda, Canadian Journal of Chemistry, 1988, vol. 66, p. 1219 - 1222

  摘要：

  DOI：

文献信息

• Enantioselective hydrolysis of 2-(chlorophenoxy)propionic esters by esterases.
  作者：Roxane Dernoncour、Robert Azerad

  DOI：10.1016/s0040-4039(00)96590-0

  日期：1987.1

  Enzymatic hydrolysis of racemic 2-(mono-,di- and trichlorophenoxy)-propionic acids methyl esters by α-chymotrypsin, pig liver esterase and porcine pancreatic or lipases was found to be poorly to moderately enantioselective; in most cases, the R-ester was preferentially hydrolyzed.

  发现α-胰凝乳蛋白酶，猪肝酯酶和猪胰或脂肪酶对外消旋2-（单，二和三氯苯氧基）-丙酸甲酯的酶促水解作用差到中等对映选择性。在大多数情况下，R酯优先水解。
• Chemoenzymatic Synthesis of Enantioenriched ( <i>R</i> )‐ and ( <i>S</i> )‐Aryloxyalkanoic Herbicides
  作者：Danilo Colombo、Alessia Albergati、Erica E. Ferrandi、Davide Tessaro、Francesco G. Gatti、Elisabetta Brenna、Daniela Monti、Fabio Parmeggiani

  DOI：10.1002/ejoc.202200609

  日期：2022.7.7

  A versatile and sustainable approach to one of the most commonly employed families of herbicides has been developed, which is based on a biocatalytic reductive dehalogenation followed by simple chemical manipulations. A range of commercially relevant target molecules have been obtained in good yield and moderate to excellent enantioselectivity (to either enantiomer), without chromatographic purifications

  对于最常用的除草剂家族之一，已经开发出一种通用且可持续的方法，该方法基于生物催化还原脱卤，然后进行简单的化学操作。一系列商业相关的目标分子已经以良好的收率和中等至极好的对映选择性（对任一对映异构体）获得，无需色谱纯化和使用粗酶制剂。
• Improvement of catalytic activity of Candida rugosa lipase in the presence of calix[4]arene bearing iminodicarboxylic/phosphonic acid complexes modified iron oxide nanoparticles
  作者：Elif Ozyilmaz、Mevlut Bayrakci、Mustafa Yilmaz

  DOI：10.1016/j.bioorg.2015.12.001

  日期：2016.4

  In the present study, iron oxide magnetite nanoparticles, prepared through a co-precipitation method, were coated with phosphonic acid or iminodicarboxylic acid derivatives of calix[4]arene to modulate their surfaces with different acidic groups. Candida rugosa lipase was then directly immobilized onto the modified nanoparticles through sol-gel encapsulation. The catalytic activities and enantioselectivities of the two encapsulated lipases in the hydrolysis reaction of (R/S)-naproxen methyl ester and (R/S)-2-phenoxypropionic acid methyl ester were assessed. The results showed that the activity and enantioselectivity of the lipase were improved when the lipase was encapsulated in the presence of calixarene-based additives; the encapsulated lipase with the phosphonic acid derivative of calix[4]arene had an excellent rate of enantioselectivity against the (R/S)-naproxen methyl and (R/S)-2-phenoxypropionic acid methyl esters, with E = 350 and 246, respectively, compared to the free enzyme. The encapsulated lipases (Fe-Calix-N(COOH)) and (Fe-Calix-P) showed good loading ability and little loss of enzyme activity, and the stability of the catalyst was very good; they only lost 6-11% of the enzyme's activity after five batches. (C) 2015 Elsevier Inc. All rights reserved.
• Stereospecific synthesis and bio-activity of novel β3-adrenoceptor agonists and inverse agonists
  作者：Maria Grazia Perrone、Ernesto Santandrea、Laura Bleve、Paola Vitale、Nicola Antonio Colabufo、Ralf Jockers、Ferdinando Maria Milazzo、Anna Floriana Sciarroni、Antonio Scilimati

  DOI：10.1016/j.bmc.2007.11.060

  日期：2008.3

  towards beta(3)-adrenoceptor and their affinity for beta(1)- and beta(2)-adrenergic receptors. Stereochemical features were found to play a crucial role in determining the behaviour of such compounds. In particular, alpha-racemic, (alphaR)- and (alphaS)-2-4-[2-(2-hydroxy-2-phenylethylamino)ethyl]phenoxy}-2- methylpropanoic acid, (alpha-rac, beta-rac)-, (alphaR, betaS)- and (alphaR, betaR)- 2-4-[2-(2-

  由于β（3）-肾上腺素能受体广泛分布于体内，因此正成为治疗多种疾病的诱人靶标，例如肥胖，2型糖尿病，代谢综合征，恶病质，膀胱过度活动症，肠道溃疡性炎症，早产，焦虑和抑郁症以及心力衰竭。以高收率制备属于具有一个或两个立体生成中心的芳基乙醇胺类的新化合物，为外消旋体和旋光形式。然后，评估他们对β（3）-肾上腺素受体的内在活性以及对β（1）-和β（2）-肾上腺素受体的亲和力。发现立体化学特征在确定此类化合物的行为中起关键作用。特别是，α-外消旋，（alphaR）-和（alphaS）-2- 4- [2-（2-（2-羟基-2-苯基乙基氨基）乙基]苯氧基} -2-甲基丙酸，（alpha-rac，beta-rac）-，（alphaR，发现βS）-和（αR，βR）-2- 4- [2-（2-（2-羟基-2-苯基乙基氨基）乙基]苯氧基}丙酸具有β（3）-肾上腺素受体激动活性。而（alphaS，betaS）-和（alphaS，betaR）-2-
• Chenevert, Robert; D'Astous, Linda, Canadian Journal of Chemistry, 1988, vol. 66, p. 1219 - 1222
  作者：Chenevert, Robert、D'Astous, Linda

  DOI：——

  日期：——