1-acetoxy-1-(6-methoxy-2-naphthyl)ethane | 261954-27-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 1-acetoxy-1-(6-methoxy-2-naphthyl)ethane
• 英文别名: (S)-(-)-1-(6-methoxynaphthalen-2-yl)ethyl acetate；[(1S)-1-(6-methoxynaphthalen-2-yl)ethyl] acetate
• CAS: 261954-27-2
• 化学式: C₁₅H₁₆O₃
• 分子量: 244.29
• InChiKey: MUCZWEHZCLXTEW-JTQLQIEISA-N

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-acetoxy-1-(6-methoxy-2-naphthyl)ethane
  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

• 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
• Green methodology for enzymatic hydrolysis of acetates in non-aqueous media via carbonate salts
  作者：Mounia Merabet-Khelassi、Zahia Houiene、Louisa Aribi-Zouioueche、Olivier Riant

  DOI：10.1016/j.tetasy.2012.06.001

  日期：2012.6

  Herein we report a new approach to enantiomerically enriched acetates using a lipase-catalyzed hydrolysis in non-aqueous media by alkaline carbonate salts. The use of sodium carbonate in the enzymatic hydrolysis with Candida antarctica lipase B (CAL-B) of racemic acetates shows a large enhancement of the reactivity and selectivity of this lipase. The role of the carbonate salts, the amount and the

  本文中，我们报告了一种新方法，可利用脂肪酶催化的非水介质中碱性碳酸盐在对映体上富集乙酸盐。在外消旋乙酸的南极假丝酵母脂肪酶B（CAL-B）的酶促水解中使用碳酸钠显示出该脂肪酶的反应性和选择性大大提高。研究了碳酸盐的作用，碱土金属的数量和性质对这种新途径的效率的影响。描述了在温和条件下通过酶促碳酸酯水解产生的乙酸酯1a – 9a的酶促动力学拆分。在所有情况下，所得到的醇和残留的乙酸盐都具有较高的ee值（高达> 99％），而选择性达到E。 > 500。
• 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。
• Trichosporon beigelli esterase (TBE): a versatile esterase for the resolution of economically important racemates
  作者：Surrinder Koul、Jawahir Lal Koul、Budh Singh、Munish Kapoor、Rajinder Parshad、Kuldeep S. Manhas、Subhash C. Taneja、Ghulam N. Qazi

  DOI：10.1016/j.tetasy.2005.07.009

  日期：2005.8

  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.
• Sampath Kumar; Joyasawal, Sipak; Reddy, Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 2005, vol. 44, # 8, p. 1686 - 1692
  作者：Sampath Kumar、Joyasawal, Sipak、Reddy、Pawan Chakravarthy、Krishna、Yadav

  DOI：——

  日期：——