(+/-)-1-methylpentyl propanoate | 149309-86-4

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: (+/-)-1-methylpentyl propanoate
• 英文别名: 1-methylpentyl propanoate；2-hexyl propionate；propionic acid-(1-methyl-pentyl ester)；Propionsaeure-(1-methyl-pentylester)；hexan-2-yl propanoate
• CAS: 149309-86-4
• 化学式: C₉H₁₈O₂
• 分子量: 158.241
• InChiKey: XOZXPRSBNBCWRN-UHFFFAOYSA-N

物化性质

• 沸点：
  176.5±8.0 °C(Predicted)
• 密度：
  0.874±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  11
• 可旋转键数：
  6
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.89
• 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：

  (+/-)-1-methylpentyl propanoate 、 2-戊醇 在 Novozym 435 作用下， 生成 2-丙酸戊醇酯
  参考文献：
  名称：

  Enhancing the enantioselectivity of CALB by substrate imprinting: A combined experimental and molecular dynamics simulation model study

  摘要：

  Kinetic resolution of pentan-2-ol by CALB catalyzed enantioselective transesterification, with various alkylpropanoate acyl donors, was studied in a solid-gas reactor. Results show that the leaving alkoxy group influences the enantiomeric ratio of the reaction. Resolution of pentan-2-ol with methyl propanoate gives an enantiomeric ratio of 62. Esters with longer linear alkyl chains, from ethyl to pentyl propanoate give higher enantiomeric ratios, comprised between 103 and 117. Enantiopure ester (R)-1-methylpentyl propanoate increases the enantiomeric ratio to 140 compared with E = 120 for the racemic mixture. In contrast, enantiopure (S)-1-methylpentyl propanoate decreases the enantiomeric ratio to 72. Our data support the notion of an imprinting effect or "ligand-induced enzyme memory" caused by the shape of the leaving alcohol. To simulate the imprinting effect caused by the alkoxy part of the acyl donor, molecular modeling studies were performed with both (R)- and (S)-enantiopure 1-methylpentyl propanoate.To investigate how the first step of the reaction, through the first tetrahedral intermediate, affects the enzyme conformation depending on the enantiopure ester substrate used, 20 ns molecular dynamics simulations were carried out. Clustering analysis was done to study relevant conformations of the systems. Differences in the global conformation of the enzyme between systems with R or S enantiomers were not observed. Interestingly however, orientation of the partially buried side chain for IIe285 was affected. This could explain the increased enantiomeric ratio observed with the substrate ester (R)-1-methylpentyl propanoate due to an improved (R)-pentan-2-ol/enzyme interaction. (C) 2012 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.molcatb.2012.04.017
• 作为产物：
  描述：

  2-己酮 在 4-二甲氨基吡啶 、 sodium tetrahydroborate 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 0.17h， 生成 (+/-)-1-methylpentyl propanoate
  参考文献：
  名称：

  Enzymatic kinetic resolution of aliphatic sec -alcohols by LipG9, a metagenomic lipase

  摘要：

  Bioprospection for new enantioselective enzymes for application in organic synthesis is a prominent area of investigation in biocatalysis. In this context, here we present the evaluation of an immobilized lipase isolated from a metagenomic library (LipG9) for the enzymatic kinetic resolution (EKR) of aliphatic sec -alcohols, which are still challenging substrates, since low enantioselectivity values are usually observed for these resolutions. LipG9 was successfully employed in EKR of aliphatic alcohols, which were resolved with satisfactory conversions (19-59%) and enantiomeric excesses for alcohols (26-88%) and esters (30-96%) by transesterification reactions, demonstrating that its performance is equal to or better than commercially available enzymes for the same reaction. (C) 2016 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.molcatb.2015.12.010

文献信息

• An extremely efficient and green method for the acylation of secondary alcohols, phenols and naphthols with a deep eutectic solvent as the catalyst
  作者：Hai Truong Nguyen、Phuong Hoang Tran

  DOI：10.1039/c6ra22757k

  日期：——

  The typical deep eutectic solvent [CholineCl][ZnCl2]3 easily prepared from choline chloride and zinc chloride is green and useful for the acylation of secondary alcohols, phenols, and naphthols with acid anhydrides....

  由氯化胆碱和氯化锌容易制备的典型深共熔溶剂[CholineCl] [ZnCl2] 3是绿色的，可用于用酸酐对仲醇，酚和萘进行酰化反应。
• Benzamidine derivatives
  申请人：SANKYO COMPANY, LIMITED

  公开号：US20040248981A1

  公开（公告）日：2004-12-09

  Benzamidine derivatives of formula (I) or pharmaceutically acceptable salts thereof exhibit excellent inhibitory activity against factor Xa and are useful for treating or preventing blood coagulation disorders: 1 wherein R 1 represents a hydrogen atom, a halogen atom, an alkyl group or a hydroxyl group; R 2 represents a hydrogen atom, a halogen atom or an alkyl group, R 3 represents a hydrogen atom, an optionally substituted alkyl group, an aralkyl group, an optionally substituted alkanoyl group or an optionally substituted alkylsulfonyl group, R 4 and R 5 are the same as or different from each other and each represent a hydrogen atom, a halogen atom, an optionally substituted alkyl group, an alkoxy group, a carboxyl-group, an alkoxycarbonyl group or an optionally substituted carbamoyl group, and R 6 represents a substituted pyrrolidine group or substituted piperidine group.

  公式（I）中的苯甲酰胺衍生物或其药学上可接受的盐表现出优异的抑制因子Xa的活性，可用于治疗或预防血液凝固障碍：其中R1代表氢原子，卤原子，烷基或羟基；R2代表氢原子，卤原子或烷基，R3代表氢原子，可选取代的烷基，芳基烷基，可选取代的烷酰基或可选取代的烷基磺酰基，R4和R5相同或不同，每个代表氢原子，卤原子，可选取代的烷基，烷氧基，羧基，烷氧羰基或可选取代的氨基甲酰基，而R6代表取代的吡咯烷基或取代的哌嗪烷基。
• BENZAMIDINE DERIVATIVES
  申请人：Sankyo Company, Limited

  公开号：EP1245564A1

  公开（公告）日：2002-10-02

  Benzamidine derivatives of formula (I) or pharmaceutically acceptable salts thereof exhibit excellent inhibitory activity against factor Xa and are useful for treating or preventing blood coagulation disorders: wherein R1 represents a hydrogen atom, a halogen atom, an alkyl group or a hydroxyl group; R2 represents a hydrogen atom, a halogen atom or an alkyl group, R3 represents a hydrogen atom, an optionally substituted alkyl group, an aralkyl group, an optionally substituted alkanoyl group or an optionally substituted alkylsulfonyl group, R4 and R5 are the same as or different from each other and each represent a hydrogen atom, a halogen atom, an optionally substituted alkyl group, an alkoxy group, a carboxyl group, an alkoxycarbonyl group or an optionally substituted carbamoyl group, and R6 represents a substituted pyrrolidine group or substituted piperidine group.

  式（I）的苯甲脒衍生物或其药学上可接受的盐类对 Xa 因子具有优异的抑制活性，可用于治疗或预防血液凝固紊乱： 其中 R1 代表氢原子、卤素原子、烷基或羟基；R2代表氢原子、卤素原子或烷基，R3代表氢原子、任选取代的烷基、芳烷基、任选取代的烷酰基或任选取代的烷磺酰基，R4和R5彼此相同或不同，各自代表氢原子、卤素原子、任选取代的烷基、烷氧基、羧基、烷氧羰基或任选取代的氨基甲酰基，R6代表取代的吡咯烷基或取代的哌啶基。
• Mutations in the stereospecificity pocket and at the entrance of the active site of Candida antarctica lipase B enhancing enzyme enantioselectivity
  作者：Z. Marton、V. Léonard-Nevers、P.-O. Syrén、C. Bauer、S. Lamare、K. Hult、V. Tranc、M. Graber

  DOI：10.1016/j.molcatb.2010.01.007

  日期：2010.8

  Two different parts of Candida antarctica lipase B (stereospecificity pocket at the bottom of the active site and hydrophobic tunnel leading to the active site) were redesigned by single- or double-point mutations, in order to better control and improve enzyme enantioselectivity toward secondary alcohols. Single-point isosteric mutations of Ser47 and Thr42 situated in the stereospecificity pocket gave rise to variants with doubled enantioselectivity toward pentan-2-ol, in solid/gas reactor. Besides, the width and shape of the hydrophobic tunnel leading to the active site was modified by producing the following single-point mutants: Ile189Ala, Leu278Val and Ala282Leu. For each of these variants a significant modification of enantioselectivity was observed compared to wild-type enzyme, indicating that discrimination of the enantiomers by the enzyme could also arise from their different accessibilities from the enzyme surface to the catalytic site. (C) 2010 Elsevier B.V. All rights reserved.
• PICOLINAMIDES WITH FUNGICIDAL ACTIVITY
  申请人：Dow Agrosciences LLC

  公开号：EP3240408B1

  公开（公告）日：2020-04-08