phenyl-2 butyrate de p-nitrophenyle | 72289-61-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚酯
• 英文名称: phenyl-2 butyrate de p-nitrophenyle
• 英文别名: 4-nitrophenyl 2-phenylbutanoate；α-Phenylbuttersaeure-p-nitrophenylester；Butyric acid, 2-phenyl-, 4-nitrophenyl ester；(4-nitrophenyl) 2-phenylbutanoate
• CAS: 72289-61-3
• 化学式: C₁₆H₁₅NO₄
• 分子量: 285.299
• InChiKey: COAYZKDYHOUBLT-UHFFFAOYSA-N

物化性质

• 沸点：
  436.0±38.0 °C(Predicted)
• 密度：
  1.222±0.06 g/cm3(Predicted)
• 保留指数：
  2315

计算性质

• 辛醇/水分配系数(LogP)：
  4
• 重原子数：
  21
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.19
• 拓扑面积：
  72.1
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  phenyl-2 butyrate de p-nitrophenyle 在 4-二甲氨基吡啶 、 Bacillus subtilis 168 SrfAD esterase 、 N,N'-二环己基碳二亚胺 作用下， 以 二甲基亚砜 为溶剂， 反应 8.05h， 生成 4-硝基苯基乙酸酯
  参考文献：
  名称：

  Fingerprint lipolytic enzymes with chromogenic p-nitrophenyl esters of structurally diverse carboxylic acids

  摘要：

  A series of structurally diverse chromogenic esters, including a new compound (4-nitrophenyl 2-methylpentanoate), has been synthesized, constituting an array of 17 substrates which could be applied to rapidly fingerprint the activity of lipases or esterases to reveal their substrates specificity and functional characteristics. Combined with genetic technology such as "data mining" and directed evolution, such fingerprints might be a promising platform for discovery of potentially useful enzymes in industrial application. The fingerprint of commercially available Lipase-B from Candida antarctica as a model enzyme was first measured to confirm the reliability of this method. Then three new enzymes mined from genomic libraries were successfully fingerprinted, revealing the functional characteristics of those enzymes. Among them, the enzyme SrfAD was founded with specific substrate preference towards cycloalkyl carboxylic esters and aromatic esters, making it more promising in synthetic utilities than other tested enzymes. (C) 2011 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.molcatb.2011.07.010
• 作为产物：
  描述：

  4-硝基苯基硬脂酸酯 在 4-二甲氨基吡啶 、 Candida antarctica lipase B 、 Bacillus subtilis 168 SrfAD esterase 、 N,N'-二环己基碳二亚胺 作用下， 以 二甲基亚砜 为溶剂， 反应 80.5h， 生成 phenyl-2 butyrate de p-nitrophenyle
  参考文献：
  名称：

  Fingerprint lipolytic enzymes with chromogenic p-nitrophenyl esters of structurally diverse carboxylic acids

  摘要：

  A series of structurally diverse chromogenic esters, including a new compound (4-nitrophenyl 2-methylpentanoate), has been synthesized, constituting an array of 17 substrates which could be applied to rapidly fingerprint the activity of lipases or esterases to reveal their substrates specificity and functional characteristics. Combined with genetic technology such as "data mining" and directed evolution, such fingerprints might be a promising platform for discovery of potentially useful enzymes in industrial application. The fingerprint of commercially available Lipase-B from Candida antarctica as a model enzyme was first measured to confirm the reliability of this method. Then three new enzymes mined from genomic libraries were successfully fingerprinted, revealing the functional characteristics of those enzymes. Among them, the enzyme SrfAD was founded with specific substrate preference towards cycloalkyl carboxylic esters and aromatic esters, making it more promising in synthetic utilities than other tested enzymes. (C) 2011 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.molcatb.2011.07.010

文献信息

• CATALYTIC ESTER DECARBONYLATION
  申请人：Tolman William Baker

  公开号：US20160194276A1

  公开（公告）日：2016-07-07

  A process of preparing olefins of the formula (I) is described herein: with R 1 being a substituted or unsubstituted (C 1 -C 30 )hydrocarbyl, and R 2 being a substituted or unsubstituted (C 1 -C 20 )hydrocarbyl. The process includes reacting a compound of formula (II) wherein Ar is chosen from in the presence of a palladium-based catalyst and an organic solvent. A process of preparing olefins of the formula (III) is also described: with R 3 being a substituted or unsubstituted (C 1 -C 30 )hydrocarbyl, R 4 being a substituted or unsubstituted (C 1 -C 20 )hydrocarbyl, and R 5 being a substituted or unsubstituted (C 1 -C 30 ) hydrocarbyl. The process includes reacting a compound of formula (IV) wherein Ar is chosen from with a compound of formula (V) wherein Ar is chosen from in the presence of a palladium-based catalyst and an organic solvent.

  本文描述了一种制备具有化学式（I）的烯烃的过程： 其中R1是取代或未取代的（C1-C30）烃基，R2是取代或未取代的（C1-C20）烃基。该过程包括在钯基催化剂和有机溶剂的存在下，反应具有化学式（II）的化合物 其中Ar选择自 。还描述了一种制备具有化学式（III）的烯烃的过程： 其中R3是取代或未取代的（C1-C30）烃基，R4是取代或未取代的（C1-C20）烃基，R5是取代或未取代的（C1-C30）烃基。该过程包括在钯基催化剂和有机溶剂的存在下，反应具有化学式（IV）的化合物 其中Ar选择自 与具有化学式（V）的化合物 其中Ar选择自 。
• Stereodivergent Protein Engineering of a Lipase To Access All Possible Stereoisomers of Chiral Esters with Two Stereocenters
  作者：Jian Xu、Yixin Cen、Warispreet Singh、Jiajie Fan、Lian Wu、Xianfu Lin、Jiahai Zhou、Meilan Huang、Manfred T. Reetz、Qi Wu

  DOI：10.1021/jacs.9b02709

  日期：2019.5.15

  Enzymatic stereodivergent synthesis to access all possible product stereoisomers bearing multiple stereocenters is relatively undeveloped, although enzymes are being increasingly used in both academic and industrial areas. When two stereocenters and thus four stereoisomeric products are involved, obtaining stereodivergent enzyme mutants for individually accessing all four stereoisomers would be ideal

  尽管酶越来越多地用于学术和工业领域，但酶促立体发散合成以获取所有可能的具有多个立体中心的产品立体异构体相对不发达。当涉及两个立体中心和四个立体异构产物时，获得立体发散酶突变体以单独访问所有四种立体异构体将是理想的。尽管在一般酶的定向进化方面取得了重大成功，但将一种酶立体发散工程化为四种高度立体互补的变体以获得带有多个立体中心的立体异构体的完整补充仍然是一个挑战。使用南极念珠菌脂肪酶 B (CALB) 作为模型，我们将这种酶的蛋白质工程报告为四种高度立体互补的变体，这些变体是在有机溶剂中外消旋酸和外消旋醇之间的酯交换反应中获得所有四种立体异构体所需的。通过生成和筛选每种异构体的少于 25 个变体，我们对模型反应中所有四种可能的立体异构体实现了 >90% 的选择性。这一困难的壮举是通过在酶结合口袋内衬的位点开发一种称为“集中合理迭代位点特异性诱变”（FRISM）的策略来完成的。使用一组有限的合
• Olefins from biomass feedstocks: catalytic ester decarbonylation and tandem Heck-type coupling
  作者：Alex John、Levi T. Hogan、Marc A. Hillmyer、William B. Tolman

  DOI：10.1039/c4cc09003a

  日期：——

  anhydride additives, the catalytic decarbonylation of p-nitrophenylesters of aliphatic carboxylic acids to their corresponding olefins, including commodity monomers like styrene and acrylates, has been developed. The reaction is catalyzed by palladium complexes in the absence of added ligands and is promoted by alkali/alkaline-earth metal halides. Combination of catalytic decarbonylation and Heck-type coupling

  为了避免需要酸酐添加剂，已经开发了将脂肪族羧酸的对硝基苯基酯催化脱羰成它们相应的烯烃，包括商品单体如苯乙烯和丙烯酸酯的方法。在不存在添加的配体的情况下，该反应由钯配合物催化，并且由碱/碱土金属卤化物促进。在单锅法中催化脱羰基和Heck型偶联与芳基酯的结合证明了在合成方法中使用羧酸作为“掩蔽烯烃”的可行性。
• Laboratory Evolution of Enantiocomplementary Candida antarctica Lipase B Mutants with Broad Substrate Scope
  作者：Qi Wu、Pankaj Soni、Manfred T. Reetz

  DOI：10.1021/ja310455t

  日期：2013.2.6

  saturation mutagenesis was applied to solve the latter problem. Mutants with highly improved activity and enantioselectivity relative to wild-type CALB were evolved for the hydrolytic kinetic resolution of p-nitrophenyl 2-phenylpropanoate, with the selectivity factor increasing from E = 1.2 (S) to E = 72 (S) or reverting to E = 42 (R) on an optional basis. Surprisingly, point mutations both in the acyl and alcohol

  南极念珠菌脂肪酶 B (CALB) 是一种强大且易于表达的酶，广泛用于学术和工业实验室，具有多种不同类型的应用。在精细化学品生产中，实例包括外消旋仲醇和胺的酰化动力学拆分以及前手性二醇的去对称化（或反向水解反应）。然而，在酯的水解动力学拆分或酸的酯化动力学拆分（其中手性存在于底物的羧酸部分）的情况下，速率和立体选择性通常较差。在本研究中，基于迭代饱和诱变的定向进化被应用于解决后一个问题。相对于野生型 CALB，具有高度改进的活性和对映选择性的突变体被进化用于对硝基苯基 2-苯基丙酸酯的水解动力学拆分，选择性因子从 E = 1.2 (S) 增加到 E = 72 (S) 或恢复到E = 42 (R) 可选。令人惊讶的是，CALB 的酰基和醇袋中的点突变被证明是必要的。一些进化的 CALB 突变体在其他手性酯的动力学解析中也是有效的生物催化剂，而无需进行新的诱变实验。另一个值得注意的结果涉及发现α-取代羧酸酯的对映互补
• Directed Evolution of an Enantioselective Lipase with Broad Substrate Scope for Hydrolysis of α-Substituted Esters
  作者：Karin Engström、Jonas Nyhlén、Anders G. Sandström、Jan-E. Bäckvall

  DOI：10.1021/ja100593j

  日期：2010.5.26

  Candida antarctica lipase A (CalA) was developed for the hydrolysis of alpha-substituted p-nitrophenyl esters by directed evolution. The E values of this variant for 7 different esters was 45-276, which is a large improvement compared to 2-20 for the wild type. The broad substrate scope of this enzyme variant is of synthetic use, and hydrolysis of the tested substrates proceeded with an enantiomeric

  南极假丝酵母脂肪酶 A (CalA) 的一种变体被开发用于通过定向进化水解 α 取代的对硝基苯酯。该变体对 7 种不同酯的 E 值为 45-276，与野生型的 2-20 相比，这是一个很大的改进。这种酶变体的广泛底物范围具有合成用途，测试底物的水解以 95-99% 的对映体过量进行。大多数底物的活性也增加了 30 倍。开发的酶变体显示 (R) 选择性，与对大多数底物具有 (S) 选择性的野生型相比，这是相反的。