(S)-1,2,3,4-tetrahydronaphthalen-1-yl acetate

• 分子结构分类: 有机化合物 - 苯类化合物 - 四氢化萘
• 英文名称: (S)-1,2,3,4-tetrahydronaphthalen-1-yl acetate
• 英文别名: [(1S)-1,2,3,4-tetrahydronaphthalen-1-yl] acetate
• 化学式: C₁₂H₁₄O₂
• 分子量: 190.242
• InChiKey: XAEPSGWPSVIKND-LBPRGKRZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  14
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (S)-1,2,3,4-tetrahydronaphthalen-1-yl acetate 在 potassium carbonate 作用下， 以 甲醇 为溶剂， 生成 (S)-(+)-1,2,3,4-四氢-1-萘酚
  参考文献：
  名称：

  一种高选择性的酯水解酶从假单胞菌。用于酶法制备对映体纯的仲醇；有机合成中的手性助剂

  摘要：

  一系列有价值的手性助剂（R）-和（S）-（1）-（11），通过在假单胞菌属脂肪酶的脂肪酶存在下酶解其酯，以高化学和光学收率制备。

  DOI：

  10.1039/c39880000598
• 作为产物：
  描述：

  1,2,3,4-四氢-1-萘酚 在 4-二甲氨基吡啶 、 偶氮二甲酸二异丙酯 、 三乙胺 、 三苯基膦 作用下， 以 aq. phosphate buffer 、 乙醚 为溶剂， 反应 72.0h， 生成 (S)-1,2,3,4-tetrahydronaphthalen-1-yl acetate
  参考文献：
  名称：

  A green route to enantioenriched (S)-arylalkyl carbinols by deracemization via combined lipase alkaline-hydrolysis/Mitsunobu esterification

  摘要：

  Herein we report results of the chemoenzymatic deracemization of a range of secondary benzylic acetates 1a-9a via a sequence of hydrolysis with CAL-B lipase in non-conventional media, combined with esterification of the recovered alcohol according to the Mitsunobu protocol following an enzymatic kinetic resolution (KR). The KR of racemic acetates 1a-9a via an enzymatic hydrolysis, with CAL-B lipase and Na2CO3, in non-aqueous media was optimized and gave high selectivities (E >> 200) at good conversions (C >49%) for all of the substrates studied. This method competes well with the traditional one performed in a phosphate buffer solution. The deracemization using Mitsunobu inversion gave the (S)-acetates in moderate to excellent enantiomeric excess 75% < ee < 99%, in acceptable isolated yields 70% < yield < 89%, and with some variations according to the acetate structure. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2013.01.020

文献信息

• Dioxygenase-catalysed oxidation of dihydronaphthalenes to yield arene hydrate and cis-dihydro naphthalenediols
  作者：Derek R. Boyd、Narain D. Sharma、Nuala A. Kerley、R. Austin S. McMordie、Gary N. Sheldrake、Paul Williams、Howard Dalton

  DOI：10.1039/p19960000067

  日期：——

  trihydroxylation and dehydrogenation. The arene hydrates, (R)-1,2-dihydronaphthalen-l-ol 5 and (R)-1,4-dihydronaphthalen-l-ol 7, were isolated as enantiopure metabolites while 1,2-dihydronaphthalen-2-ol 8 was found in almost racemic form. The structure, enantiopurity and absolute stereochemistry of these arene hydrates of naphthalene were confirmed by chemical synthesis. Deuterium labelling studies,

  使用恶臭假单胞菌UV4的生长培养物对1,2-和1,4-二氢萘底物进行生物转化，导致双加氧酶催化的苄基单羟基化，顺式-四氢二醇和顺式-二氢二醇的形成，三羟基化和脱氢。芳烃水合物，（R）-1,2-二氢萘-1-醇5和（R）-1,4-二氢萘-1-醇7被分离为对映体纯代谢产物，而1,2-二氢萘-2-醇8几乎呈外消旋形式。这些萘芳烃水合物的结构，对映体纯度和绝对立体化学通过化学合成得到证实。氘标记研究，以及使用对映体纯的芳烃水合物5和7作为底物，用于建立形成（1 R，2 S）-1,2-二氢萘-1,2-二醇2的代谢途径。来自1,2-二氢萘3和1,4-二氢萘6的底物。
• Identification of an Esterase Isolated Using Metagenomic Technology which Displays an Unusual Substrate Scope and its Characterisation as an Enantioselective Biocatalyst
  作者：Declan P. Gavin、Edel J. Murphy、Aoife M. Foley、Ignacio Abreu Castilla、F. Jerry Reen、David F. Woods、Stuart G. Collins、Fergal O'Gara、Anita R. Maguire

  DOI：10.1002/adsc.201801691

  日期：2019.6.6

  Evaluation of an esterase annotated as 26D isolated from a marine metagenomic library is described. Esterase 26D was found to have a unique substrate scope, including synthetic transformations which could not be readily effected in a synthetically useful manner using commercially available enzymes. Esterase 26D was more selective towards substrates which had larger, more sterically demanding substituents

  描述了评估从海洋宏基因组库中分离为26D的酯酶的方法。发现酯酶26D具有独特的底物范围，包括使用市售酶不易以合成有用的方式实现的合成转化。酯酶26D是更具选择性的朝向具有较大的，更空间要求的取代基的底物（即，异-丙基或叔-丁基基团）上的β碳，这是相对于其中显示的偏好基板与空间位先前测试的市售的酶β-碳原子上的取代基（例如甲基）要求较低。
• Entrapment of Pseudomonas cepacia lipase with peracetylated β-cyclodextrin in sol–gel: application to the kinetic resolution of secondary alcohols
  作者：Ashraf Ghanem、Volker Schurig

  DOI：10.1016/s0957-4166(03)00550-0

  日期：2003.9

  cepacia lipase with peracetylated β-cyclodextrin was immobilized by the sol–gel process. The gel-entrapped lipase/cyclodextrin was prepared by the hydrolysis of methyltrimethoxysilane (MTMS) in the presence of the co-lyophilized lipase with peracetylated β-cyclodextrin prepared with different weight ratios (enzyme to CD). This type of enzyme preparation was subsequently used in the kinetic resolution

  共冻干洋葱假单胞菌过乙酰化β-环糊精的脂肪酶通过溶胶-凝胶法固定化。凝胶包裹的脂肪酶/环糊精是在共冻干脂肪酶与过乙酰化的β-环糊精共存的条件下，通过甲基三甲氧基硅烷（MTMS）的水解而制得的，所述过乙酰化的β-环糊精以不同的重量比（酶与CD）制备。这种类型的酶制剂随后用于动力学拆分一组仲醇，其中乙酸异丙烯酯作为甲苯中无害的酰基供体，作为有机介质。使用气相色谱法在新的手性固定相（CSP）Chirasil-β-Dex上含有十一碳亚甲基间隔基（C11-Chirasil-Dex）的情况下，在不进行衍生化的情况下，将分析中得到的手性醇（底物）和相应的乙酸盐（产物）进行基线分离。 。
• 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。