(S)-2-benzoylamino-γ-butyrolactone | 40856-55-1

• 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: (S)-2-benzoylamino-γ-butyrolactone
• 英文别名: N-benzoyl-L-homoserine-lactone；N-Benzoyl-L-homoserin-lacton；N-[(3S)-2-oxooxolan-3-yl]benzamide
• CAS: 40856-55-1
• 化学式: C₁₁H₁₁NO₃
• 分子量: 205.213
• InChiKey: HUNZJKFFMPFZTC-VIFPVBQESA-N

物化性质

• 沸点：
  504.0±43.0 °C(Predicted)
• 密度：
  1.26±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.3
• 重原子数：
  15
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  55.4
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (S)-2-benzoylamino-γ-butyrolactone 在 sodium tetrahydroborate 作用下， 以 乙醇 为溶剂， 反应 6.0h， 以95%的产率得到(S)-N-(1,4-二羟基-2-丁基)苯甲酰胺
  参考文献：
  名称：

  Expeditious novel routes to enantiopure 3-amino tetrahydrofuran hydrochloride

  摘要：

  The synthesis of chemically and enantiomerically pure (S)-3-amino tetrahydrofuran hydrochloride starting from the natural amino acids, L-aspartic acid or L-methionine is described. The process involves no chromatography and can be easily carried out on a large scale. The enantiopurity of the final product was established by NMR and chiral HPLC methods. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2013.04.007
• 作为产物：
  描述：

  N-benzoyl-L-homoserine 在 盐酸 作用下， 生成 (S)-2-benzoylamino-γ-butyrolactone
  参考文献：
  名称：

  D-和L-高丝氨酸的制备。

  摘要：

  DOI：

  10.1021/ja01185a025

文献信息

• Studies toward the Synthesis of (+)-Palustrine:  The First Asymmetric Synthesis of (−)-Methyl Palustramate
  作者：Steven R. Angle、Robert M. Henry

  DOI：10.1021/jo980749g

  日期：1998.10.1

  (+)-palustrine, is described. The key step of the synthesis is a conformationally restricted Claisen rearrangement to afford the highly functionalized 1-benzylpipecolic ester 10. In addition, a new procedure for debenzylation of 1-benzylpiperidines (Li, (NH(2)CH(2))(2), Et(3)N, THF) was used to remove the benzyl protecting group where traditional methods failed.

  描述了（-）-甲基戊酸酯的立体选择性合成，这是合成（+）-芦丁碱的可能中间体。合成的关键步骤是构象受限的克莱森重排，以提供高度官能化的1-苄基哌酸酯10。此外，1-苄基哌啶（Li，（NH（2）CH（2））（2 ），Et（3）N，THF）用于除去传统方法失败的苄基保护基。
• n → π* Interactions in N-Acyl Homoserine Lactone Derivatives and Their Effects on Hydrolysis Rates
  作者：Daniel J. Schmucker、Sydney R. Dunbar、Tricia D. Shepherd、Michael A. Bertucci

  DOI：10.1021/acs.jpca.8b12266

  日期：2019.4.4

  The data obtained support that an increase in n → π* energy (En→π*) correlates to a decrease in the hydrolysis rate constant (kobs). Further, the observed variation in these rates demonstrates that AHL hydrolysis can be modified by manipulating steric and electronic effects that alter the electrophilicity of the lactone carbonyl. These results help to elucidate nature’s choice of AHLs as agents of density-dependent

  N-酰基高丝氨酸内酯（AHLs）通过群体感应（QS）介导革兰氏阴性细菌的整个人群行为变化，该过程显示出调节毒力，生物膜形成和其他影响人类健康的表型的过程。已提出AHL包含n→π*相互作用，该相互作用降低了分子通过内酯水解使信号失活的敏感性。在这项工作中，通过气相DFT计算，隐式溶剂DFT计算和MD模拟对7种AHL衍生物进行了建模。然后合成每种衍生物并进行水解，以探索轨道相互作用强度与水解速率之间的关系。获得的数据支持n→π*能量的增加（E n→π*）与水解速率常数（k的减小）相关obs）。此外，观察到的这些速率的变化表明，可以通过控制改变内酯羰基的亲电子性的空间和电子效应来修饰AHL水解。这些结果有助于阐明自然界对AHLs作为密度依赖性细菌传播媒介的选择，并可能为基于AHL的群体感应调节剂的设计提供参考。
• Diastereoselective addition of α-hydroxyalkyl and α-alkoxyalkyl radicals to chiral 4-methyleneoxazolidin-5-ones
  作者：Stephen G. Pyne、Karl Schafer

  DOI：10.1016/s0040-4020(98)00259-2

  日期：1998.5

  A method for preparing optically active homoserine derivatives via the photoinduced radical additions of alcohols and ethers to the chiral 4-methyleneoxazolidin-5-ones 1 and 2 has been achieved. These photoadducts, however, are readily prone to epimerization under the conditions required for their deprotection. (C) 1998 Elsevier Science Ltd. All rights reserved.
• Kitagawa, Journal of Biochemistry, 1936, vol. 24, p. 107,109
  作者：Kitagawa

  DOI：——

  日期：——
• MODULATION OF BACTERIAL QUORUM SENSING WITH SYNTHETIC LIGANDS
  申请人：WISCONSIN ALUMNI RESEARCH FOUNDATION

  公开号：US20150080349A1

  公开（公告）日：2015-03-19

  The present invention provides compounds and methods for modulation of the quorum sensing of bacteria. In an embodiment, the compounds of the present invention are able to act as replacements for naturally occurring bacterial quorum sensing ligands in a ligand-protein binding system; that is, they imitate the effect of natural ligands and produce an agonistic effect. In another embodiment, the compounds of the present invention are able to act in a manner which disturbs or inhibits the naturally occurring ligand-protein binding system in quorum sensing bacteria; that is, they produce an antagonistic effect. The compounds of the present invention comprise N-acylated-homoserine lactones (AHLs) comprised of a wide range of acyl groups.