1-(6-甲氧基萘-2-基)乙酸乙酯 | 108781-66-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 中文名称: 1-(6-甲氧基萘-2-基)乙酸乙酯
• 英文名称: (R)-1-(6-methoxynaphthalen-2-yl)ethyl acetate
• 英文别名: [(1R)-1-(6-methoxynaphthalen-2-yl)ethyl] acetate
• CAS: 108781-66-4
• 化学式: C₁₅H₁₆O₃
• 分子量: 244.29
• InChiKey: MUCZWEHZCLXTEW-SNVBAGLBSA-N

物化性质

• 沸点：
  356.0±17.0 °C(Predicted)
• 密度：
  1.122±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  18
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.27
• 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：

  1-(6-甲氧基萘-2-基)乙酸乙酯 在 氢氧化钾 作用下， 以 甲醇 为溶剂， 生成 R-1-[6-甲氧基-2-萘基]羟基乙烷
  参考文献：
  名称：

  兔胃脂肪酶介导仲醇的动力学拆分

  摘要：

  通过兔子胃脂肪酶介导的乙酸异丙烯酯基的酰化反应动力学拆分仲苄醇。在所有测试的底物中，仅对1- [2-（6-甲氧基）萘基]乙醇3a（E > 500）观察到高对映选择性。烯丙醇14a和15a也得到了有效拆分（分别为E = 26和51）。

  DOI：

  10.1016/s0040-4039(97)00242-6
• 作为产物：
  描述：

  1-(6-甲氧基-2-萘甲基)乙醇 在 4-二甲氨基吡啶 、 Trichosporon beigelli esterase 作用下， 以 phosphate buffer 为溶剂， 反应 16.08h， 生成 1-(6-甲氧基萘-2-基)乙酸乙酯
  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

• Ruthenium-catalyzed stereospecific benzylic alkylation of optically active benzyl esters with malonate nucleophiles
  作者：Hiroaki Tsuji、Koki Suzuki、Motoi Kawatsura

  DOI：10.1016/j.tetlet.2021.152947

  日期：2021.4

  The transition metal-catalyzed stereospecific benzylic alkylation of optically active benzyl esters with active methylene compounds remains extremely rare. Herein, we describe the study for the ruthenium-catalyzed benzylic alkylation of chiral benzyl esters with malonates as a carbon nucleophile. A combination of [Cp*RuCl2]2 and picolinic acid found to be effective for the title reaction, providing

  旋光性苄基酯与活性亚甲基化合物的过渡金属催化的立体有择性苄基烷基化仍然极为罕见。在这里，我们描述了手性苄酯与丙二酸酯作为碳亲核试剂的钌催化苄烷基化的研究。发现[Cp * RuCl 2 ] 2和吡啶甲酸的组合对于标题反应是有效的，提供手性苄基烷基化产物，并且保留了起始原料的立体化学。我们提出钌催化将通过双重转化机制进行。
• CAL-B-Catalyzed Enantioselective Deacetylation of Some Benzylic Acetate Derivatives Via Alcoholysis in Non-aqueous Media
  作者：Amna Zaïdi、Mounia Merabet-Khelassi、Louisa Aribi-Zouioueche

  DOI：10.1007/s10562-014-1470-7

  日期：2015.4

  Abstract Enantioselective deacetylation of a set of benzylic acetates via alcoholysis catalyzed by Lipase B from Candida antarctica (CAL-B), under mild conditions is described. A systematic study allows to determine the appropriate combination nucleophile/organic solvent and also to explain the influence of these parameters on the enzymatic catalytic reaction. In all cases, (R)-alcohols are obtained

  摘要 描述了在温和条件下通过来自南极念珠菌 (CAL-B) 的脂肪酶 B 催化的醇解对一组苄基乙酸酯进行对映选择性脱乙酰化。系统研究可以确定合适的亲核试剂/有机溶剂组合，并解释这些参数对酶催化反应的影响。在所有情况下，在转化率 36 % < C < 48 %、选择性达到 E > 500 时，获得的 (R)-醇具有高 ee（高达 >99%）。酶促反应性受溶剂疏水性和亲核试剂的结构/性质。此外，CAL-B 允许在非水介质中的酯交换之间进行对映互补：醇解和乙酰化。图形摘要
• On the use of succinic anhydride as acylating agent for practical resolution of aryl–alkyl alcohols through lipase-catalyzed acylation
  作者：Nassima Bouzemi、Hanane Debbeche、Louisa Aribi-Zouioueche、Jean-Claude Fiaud

  DOI：10.1016/j.tetlet.2003.10.208

  日期：2004.1

  recorded in the lipase-catalyzed resolution of a series of secondary aryl–alkyl alcohols with enol esters versus succinic anhydride. Whereas all the substrates could be resolved by a proper choice of the lipase/enol ester couple with moderate (E=50) to good (E>100) enantioselectivities, only some of them showed satisfactory enantioselectivity (E>50) with the use of succinic acid as acylating agent. Notably

  对脂肪酶催化的一系列仲芳基烷基醇与烯醇酯和琥珀酸酐的脂肪酶催化拆分所记录的E值进行了比较。而所有基板可以由脂肪酶/烯醇酯几个适当选择中等（解决Ë = 50），以良好的（È > 100）的对映选择性，仅它们中的一些显示出令人满意的对映选择性（Ë > 50）配合使用的琥珀酸作为酰化剂。值得注意的是，吲哚醇和1-喹啉-3-基-乙醇以实用的方式拆分，分别为E > 100和E > 80。
• Lipase-catalyzed irreversible transesterification using enol esters: XAD-8 immobilized lipoprotein lipase-catalyzed resolution of secondary alcohols
  作者：Shu-Hui Hsu、Shihn-Sheng Wu、Yi-Fong Wang、Chi-Huey Wong

  DOI：10.1016/s0040-4039(00)97076-x

  日期：1990.1

  Procedures for the preparation of XAD-8 immobilized lipoprotein lipase and the resolution of secondary alcohols of synthetic value in organic solvents using this immobilized enzyme have been developed.

  已经开发了制备XAD-8固定化脂蛋白脂肪酶的程序，以及使用该固定化酶在有机溶剂中拆分具有合成价值的仲醇的方法。
• Fluorogenic kinetic assay for high-throughput discovery of stereoselective ketoreductases relevant to pharmaceutical synthesis
  作者：Yen-Chi Thai、Anna Szekrenyi、Yuyin Qi、Gary W. Black、Simon J. Charnock、Wolf-Dieter Fessner

  DOI：10.1016/j.bmc.2017.05.024

  日期：2018.4

  aldo/keto reductase (KRED) enzymes, which allow the highly sensitive and reliable determination of activity and kinetic constants of known and unknown enzymes, as well as an immediate enantioselectivity typing. Because of its simplicity in microtiter plate format, the assay qualifies for the discovery of novel KREDs of yet unknown specificity among this vast enzyme superfamily. The suitability of this approach

  对映体纯的1-（6-甲氧基萘-2-基）和1-（6-（二甲氨基）萘-2-基）甲醇是醛基/酮还原酶（KRED）酶的荧光底物，可以高度灵敏和可靠地进行测定已知和未知酶的活性和动力学常数，以及立即的对映选择性分型。由于其微量滴定板形式的简单性，该测定符合在这个庞大的酶超家族中发现特异性未知的新型KRED的资格。通过从宏基因组学方法排列的大量短链脱氢酶/还原酶（SDR）酶的示例性筛选，说明了该方法对酶分型的适用性。