2-(2-萘氧基)丙酸乙酯 | 57416-30-5

• 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: 2-(2-萘氧基)丙酸乙酯
• 英文名称: 2-(naphthalene-2-yloxy)propionic acid ethyl ester
• 英文别名: ethyl 2-(2-naphthoxy)propanoate；(+/-)-2-[2]naphthyloxy-propionic acid ethyl ester；2-[2]naphthyloxy-propionic acid ethyl ester；(+/-)-2-[2]Naphthyloxy-propionsaeure-aethylester；α-(β-Naphthoxy)-propionsaeure-aethylester；2-[2]Naphthyloxy-propionsaeure-aethylester；Ethyl 2-(2-naphthyloxy)propanoate；ethyl 2-naphthalen-2-yloxypropanoate
• CAS: 57416-30-5
• 化学式: C₁₅H₁₆O₃
• mdl: MFCD03074370
• 分子量: 244.29
• InChiKey: VSAWAOOUWFMADO-UHFFFAOYSA-N

物化性质

• 熔点：
  52-53 °C
• 沸点：
  360.9±15.0 °C(Predicted)
• 密度：
  1.123±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  18
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.266
• 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：

  2-(2-萘氧基)丙酸乙酯 在 盐酸 、 一水合肼 、 三乙胺 、 potassium hydroxide 作用下， 以 乙醇 、 溶剂黄146 为溶剂， 反应 6.0h， 生成
  参考文献：
  名称：

  Goveas, Janet; Khader; Kalluraya, Indian Journal of Heterocyclic Chemistry, 2015, vol. 24, # 3, p. 299 - 304

  摘要：

  DOI：
• 作为产物：
  描述：

  2-(2-萘氧基)丙酸 在 吡啶 、 氯化亚砜 作用下， 以 二氯甲烷 、 苯 为溶剂， 生成 2-(2-萘氧基)丙酸乙酯
  参考文献：
  名称：

  Trichosporon beigelli esterase (TBE): a versatile esterase for the resolution of economically important racemates

  摘要：

  A hydrolase producing strain Trichosporon beigelli esterase (TBE) isolated from local cottage cheese in its native form has displayed versatility and high efficacy in the kinetic resolution of a wide range of economically important substrates, which include racemic secondary alcohols, such as 1-(6-methoxy-2-naphtliyl)ethanol (E similar to 316), 1-(3,4-methylenedioxyphenyl)ethanol and pentanol (E similar to 180 and 156 resp.), and alkyl esters of carboxylic acids such as ibuprofen (E similar to 340), 2-(benzylthio)propanoic acid (E similar to 1000). In other substrates such as in the primary alcohol 2-(6-methoxy-2-naphthyl)propan-1-ol and carboxylic acids such as 2-(5-bromo-6-methoxy-2-naphthyl)propanoic acid, 2-(2-naphthyloxy)propanoic acid, and substituted 2-thiopropanoic acids, it displayed moderate to low selectivity. Commercial lipases such as CCL, PPL, and PSL were also used in the resolution of the substrates for comparative studies. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2005.07.009

文献信息

• Microbial Deracemization of α-Substituted Carboxylic Acids:  Substrate Specificity and Mechanistic Investigation
  作者：Dai-ichiro Kato、Satoshi Mitsuda、Hiromichi Ohta

  DOI：10.1021/jo034253x

  日期：2003.9.1

  A new enzymatic method for the preparation of optically active alpha-substituted carboxylic acids is reported. This technique is called deracemization reaction, which provides us with a route to obtain the enantiomerically pure compounds, theoretically in 100% yield starting from the racemic mixture. This means that the synthesis of a racemate is almost equal to the synthesis of the optically active

  报道了一种用于制备旋光的α-取代的羧酸的新的酶促方法。这项技术称为脱硝反应，它为我们提供了从外消旋混合物开始，理论上以100％的收率获得对映体纯化合物的途径。这意味着外消旋体的合成几乎与旋光化合物的合成相同，并且该概念与不对称合成中通常被接受的概念完全不同。使用不断增长的诺卡氏夜蛾诺卡氏菌JCM3208的细胞系统，可以使2-芳基-和2-芳基氧基丙酸的外消旋物顺利脱硫，并以高化学收率（> 50％）回收富含（R）-形式的产物。此外，使用旋光性起始化合物和氘代衍生物以及抑制剂，
• Reshaping the active pocket of esterase Est816 for resolution of economically important racemates
  作者：Xiaolong Liu、Meng Zhao、Xinjiong Fan、Yao Fu

  DOI：10.1039/d1cy01028j

  日期：——

  mutants, Est816-M3 and Est816-M4, successfully overcame and even reversed the low enantioselectivity, and several 2-arylpropionic acid derivatives with high E values were obtained. Our results offer potential industrial biocatalysts for the preparation of structurally diverse chiral carboxylic acids and further lay the foundation for improving the catalytic efficiency and enantioselectivity of esterases.

  细菌酯酶是生产光学纯化合物的潜在生物催化剂。然而，酯酶的底物混杂性和手性选择性通常呈负相关，限制了它们的商业价值。在此，一种高效且多功能的酯酶 (Est816) 被确定为一种有前途的催化剂，可用于水解各种具有低对映选择性的经济上重要的底物。我们合理地设计了几种变体，对 2-芳基丙酸乙酯的催化效率提高了 11 倍，主要保留了初始底物范围和对映选择性。这些变体显着提高了生物催化应用的效率。基于最佳变体 Est816-M1，通过对结构信息和分子对接的仔细分析，设计了几种具有更高或反向对映选择性的变体。两个立体选择性互补突变体 Est816-M3 和 Est816-M4 成功克服甚至逆转了低对映选择性，以及几种具有高对映选择性的 2-芳基丙酸衍生物获得了E值。我们的研究结果为制备结构多样的手性羧酸提供了潜在的工业生物催化剂，并进一步为提高酯酶的催化效率和对映选择性奠定了基础。
• 10.1039/d4ob00938j
  作者：Yashmin, Sabina、Karthik、Khan, Abu Taleb

  DOI：10.1039/d4ob00938j

  日期：——

  Herein, we disclose the synthesis of a variety of disubstituted fused quinoline, such as 4-methyl-2-arylbenzo[h]quinolines (3a–j), 1-methyl-3-arylbenzo[f]quinolines (3k–r), 1-methyl-3-arylnaphtho[2,3-f]quinolines (3s–x), and 2-aryl-5,7-dimethoxy-4-methylquinolines (4a–c), derivatives from the reaction of an aryl aldehyde with 1-naphthylamine (1a), 2-naphthylamine (1b), 2-aminoanthracene (1c) and 3

  在此，我们公开了多种二取代稠合喹啉的合成，例如4-甲基-2-芳基苯并[ h ]喹啉( 3a–j )、1-甲基-3-芳基苯并[ f ]喹啉( 3k–r )、 1-甲基-3-芳基萘并[2,3- f ]喹啉 ( 3s–x ) 和 2-芳基-5,7-二甲氧基-4-甲基喹啉 ( 4a–c )，是芳基醛与分别为 1-萘胺 ( 1a )、2-萘胺 ( 1b )、2-氨基蒽 ( 1c ) 和 3,5-二甲氧基苯胺 ( 1d )，在 80 °C 下，在 30 mol% (±)-10-樟脑磺酸存在下使用 DMSO 作为溶剂兼反应物生成酸 ((±)-CSA)。在这个独特的反应中，DMSO 分子区域选择性地将三个碳原子结合到目标分子中。本方案的其他优点是它可以在温和的反应条件下进行，并且不需要金属催化剂、额外的添加剂或氧化剂。
• Design, synthesis and hypolipidemic activity of novel 2-(naphthalen-2-yloxy)propionic acid derivatives as desmethyl fibrate analogs
  作者：Gamal A. Idrees、Omar M. Aly、Gamal El-Din A.A. Abuo-Rahma、M.F. Radwan

  DOI：10.1016/j.ejmech.2009.04.026

  日期：2009.10

  A series of 2-(naphthalen-2-yloxy)propionic acid derivatives were prepared. The hypolipidemic activity of the new compounds as well as the intermediate acid 2 was evaluated in the high cholesterol diet (HCD) fed hyperlipidemic rat model. Interestingly, the 5-alkylated mercaptotriazole 8b and the 1,3,4-oxadiazole 9 produced striking reduction of serum levels of total cholesterol (TC), triglycerides (TGs) and low-density lipoproteins (LDLs) and elevation of serum high-density lipoproteins (HDLs) being more active than the reference gemfibrozil. In addition, the 1,2,4-triazole 7a, the hydroxypyrazoline 10 and the pyrazolone derivative 11 exhibited good hypolipidemic activity on different lipid parameters. (C) 2009 Elsevier Masson SAS. All rights reserved.
• Bischoff, Chemische Berichte, 1900, vol. 33, p. 1395
  作者：Bischoff

  DOI：——

  日期：——