(S)-4,4,4-trifluoro-3-phenylbutyn-3-yl acetate | 165657-98-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: (S)-4,4,4-trifluoro-3-phenylbutyn-3-yl acetate
• 英文别名: (-)-1,1,1-trifluoro-2-phenylbut-3-yn-2-yl acetate；1,1,1-trifluoro-2-phenylbut-3-yn-1-yl acetate；[(2R)-1,1,1-trifluoro-2-phenylbut-3-yn-2-yl] acetate
• CAS: 165657-98-7
• 化学式: C₁₂H₉F₃O₂
• 分子量: 242.197
• InChiKey: FCXGEAKJCYLMID-LLVKDONJSA-N

物化性质

• 沸点：
  240.4±40.0 °C(Predicted)
• 密度：
  1.256±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  17
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (S)-4,4,4-trifluoro-3-phenylbutyn-3-yl acetate 在 Bacillus sp. esterase EstBP₇-AGA mutant 作用下， 以 二甲基亚砜 为溶剂， 反应 2.0h， 生成 (R)-4,4,4-trifluoro-3-phenyl-3-hydroxybutyne 、 (S)-4,4,4-trifluoro-3-phenyl-3-hydroxybutyne
  参考文献：
  名称：

  通过改进的芽孢杆菌属（Bacillus sp。）的酯酶变体从仲和叔苄基炔丙醇中酯的动力学拆分。BP-7

  摘要：

  我们在最近的工作中描述了芽孢杆菌属的酯酶的合理改进。BP7旨在研究几种酯酶变体对叔醇乙酸酯的对映异构体拆分的效率。变异的EstBP7-AGA在氧阴离子孔中带有两个氨基酸变化，显示出优异的E 在低反应温度（4°C）下对复杂的乙酸叔醇乙酸酯（2-（4-吡啶基）-3-丁炔-2-基乙酸酯）的对映选择性> 100。我们通过分析苄基炔丙基酯的动力学拆分来进一步研究此类酯酶变体，以证明该酶是获得对映体纯的叔醇和仲醇的强大工具，前提是母体苄基炔丙基酯的结构完整性维持酯。了解这种酯酶变体与被测底物的作用方式和相互作用，将使人们产生有趣的药物基础。

  DOI：

  10.1016/j.cattod.2014.12.041
• 作为产物：
  描述：

  1,1,1-trifluoro-2-phenylbut-3-yn-2-yl acetate 生成 (S)-4,4,4-trifluoro-3-phenylbutyn-3-yl acetate
  参考文献：
  名称：

  Cross-Linked Crystals of Candida rugosa Lipase: Highly Efficient Catalysts for the Resolution of Chiral Esters

  摘要：

  To date, most enzyme-based organic syntheses have employed enzymes in the form. of a crude protein extract. The instability and expense of highly purified proteins has all but obviated their use as catalysts for enantioselective hydrolyses. Herein, we describe the use of the major hydrolase from commercial Candida rugosa lipase (CRL) in the form of a cross-linked enzyme crystal (CLEC) for the enantioselective hydrolysis of chiral racemic esters. The enantioselectivity of CRL-CLECs in the hydrolysis of many important chiral esters is vastly superior to that of the crude CRL extract. Since the CRL-CLEC is insoluble, recoverable, and 2-3 orders of magnitude more stable than the soluble protein, the CRL-CLEC is an attractive replacement for the crude enzyme preparation. The use of this catalyst in the resolution of chiral esters 1-11 and in the preparative scale (la):and multicycle resolution (2a) of important anti-inflammatory drugs is described.

  DOI：

  10.1021/ja00131a006

文献信息

• Highly Enantioselective Synthesis of Arylaliphatic Tertiary Alcohols using Mutants of an Esterase fromBacillus subtilis
  作者：Robert Kourist、Sebastian Bartsch、Uwe T. Bornscheuer

  DOI：10.1002/adsc.200600641

  日期：2007.6.4

  kinetic resolution of a series of acetates of arylaliphatic tertiary alcohols was studied using recombinant esterase variants from Bacillus subtilis (BS2) expressed in E. coli. Highest enantioselectivities (E>100) were achieved in the synthesis of 1,1,1-trifluoro-2-phenylbut-3-yn-2-ol and three para-substituted analogues using BS2 mutant G105A. With mutant E188D only two compounds were converted with

  使用在大肠杆菌中表达的枯草芽孢杆菌（BS2）的重组酯酶变体研究了芳基脂族叔醇一系列乙酸盐的动力学拆分。使用BS2突变体G105A合成1,1,1-三氟-2-苯基丁-3-yn-2-ol和三个对位取代的类似物可实现最高对映选择性（E> 100）。对于突变体E188D，只有两种化合物的E> 100转化了。对于噻吩类似物或在脂肪族链中具有小的变化的化合物，观察到明显较低的转化率和/或对映选择性，这也随所使用的BS2变体而变化。因此，底物结构的微小变化和酯酶中的点突变对活性和对映选择性均具有显着影响。
• O'Hagan, David; Zaidi, Naveed A., Journal of the Chemical Society. Perkin transactions I, 1992, # 8, p. 947 - 949
  作者：O'Hagan, David、Zaidi, Naveed A.

  DOI：——

  日期：——
• Characterization of a novel esterase isolated from intertidal flat metagenome and its tertiary alcohols synthesis
  作者：Ki-Hoon Oh、Giang-Son Nguyen、Eun-Young Kim、Robert Kourist、Uwe Bornscheuer、Tae-Kwang Oh、Jung-Hoon Yoon

  DOI：10.1016/j.molcatb.2012.04.015

  日期：2012.8

  A gene coding for an esterase (EstEH112) was isolated from metagenome originated from Korean intertidal flat sediment. The putative esterase gene encoded a 340 amino acids protein with characteristic residues of lipolytic enzymes such as a conserved pentapeptide (GXSXG), the typical catalytic S-D-H triad, and a GGG(A)X-motif in the oxyanion hole near the active site similar to the hormone sensitive lipase (HSL) family. p-Nitrophenyl butyrate was the best substrate for the enzyme among the other p-nitrophenyl esters investigated. The apparent optimal temperature and pH for EstEH112 was 35 C and at pH 8.0, respectively. EstEH112 efficiently catalyzed the hydrolysis of various large tertiary alcohol esters. These characteristics of EstEH112 make it a potential candidate for application in biocatalysis. (C) 2012 Elsevier B.V. All rights reserved.
• Hydrolase-catalyzed stereoselective preparation of protected α,α-dialkyl-α-hydroxycarboxylic acids
  作者：Robert Kourist、Giang-Son Nguyen、Dirk Strübing、Dominique Böttcher、Klaus Liebeton、Christian Naumer、Jürgen Eck、Uwe T. Bornscheuer

  DOI：10.1016/j.tetasy.2008.07.005

  日期：2008.8

  The title compounds were prepared by a Passerini multi-component reaction and subjected to enzymatic kinetic resolution using 40 enzymes known to be active towards esters of tertiary alcohols. This identified a protease (P]), a thermophilic esterase (PestE) and an esterase of metagenome origin (esterase 8) as the most active and enantioselective biocatalysts. After further optimization of reaction conditions, two compounds were prepared in preparative scale using esterase 8 yielding (+)-1-(tert-butylamino)-2-methyl-l-oxobutyl-2-yl acetate with 93%ee and (-)-1-(tert-butylamino)-2-trifluofo-methyl-1-oxobutyl-2-yl acetate with 47%ee. (C) 2008 Elsevier Ltd. All rights reserved.
• Complete Inversion of Enantioselectivity towards Acetylated Tertiary Alcohols by a Double Mutant of aBacillus Subtilis Esterase
  作者：Sebastian Bartsch、Robert Kourist、Uwe T. Bornscheuer

  DOI：10.1002/anie.200704606

  日期：2008.2.8