α-Phenylacetamido-γ-Butyrolactone | 500720-04-7

• 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: α-Phenylacetamido-γ-Butyrolactone
• 英文别名: N-(2-oxo-tetrahydrofuran-3-yl)-2-phenylacetamide；alpha-Phenylacetamido-gamma-butyrolactone；N-(2-oxooxolan-3-yl)-2-phenylacetamide
• CAS: 500720-04-7
• 化学式: C₁₂H₁₃NO₃
• mdl: MFCD24388166
• 分子量: 219.24
• InChiKey: YJTHUPUWKQRCLF-UHFFFAOYSA-N

物化性质

• 熔点：
  124-126 °C
• 沸点：
  518.8±49.0 °C(Predicted)
• 密度：
  1.22±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.2
• 重原子数：
  16
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.333
• 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：

  α-Phenylacetamido-γ-Butyrolactone 在 palladium on activated charcoal 2,6-二甲基吡啶 、 氢氧化钾 、 氢气 、 trifluoromethanesulfonic acid anhydride 、 三乙胺 、 N,N'-二环己基碳二亚胺 、 甲基肼 作用下， 以 甲醇 、 二氯甲烷 、 乙酸乙酯 、 N,N-二甲基甲酰胺 、 乙腈 为溶剂， 反应 150.0h， 生成 rac-homolactivicin
  参考文献：
  名称：

  Cyclic hydroxamates, especially multiply substituted [1,2]oxazinan-3-ones

  摘要：

  报道了将假定的N-酰-D-阿拉-D-阿拉替代物的合成途径，从将4、5和6元环内酯转化为5、6和7元环氢氧化物开始。合成的关键步骤是ω-氨氧酯的三甲基铝促进的环化反应。7元环氢氧化物以椅式构象结晶。将反应序列扩展到同型丝氨酸或同型丝氨酸内酯会导致环康纳林和N-酰化环康纳林的形成。环康纳林的4-苯乙酰氨基衍生物以船式构象结晶。在环康纳林的4-酰氨基环康纳林的环氮上附加2-羧基丙基取代基，可以通过将无环氨氧酯前体与苄乳酸三甲酯的三氟甲磺酸酯偶联，或在环化之后，通过与三氟甲基丙酸叔丁酯在氟化钾-氧化铝存在下偶联，然后在每种情况下去除保护基来实现。通过4-苯乙酰氨基环康纳林与苄基2-氧戊二酸酯在异亚胺存在下反应，然后进行氢解，合成了抗生素拉维西汀的六元同系物。从甲基2,4-二溴-2,4-二去氧-L-赤葡萄糖酸甲酯开始，该物质可以从抗坏血酸中经过两步合成，这些反应序列已被应用于立体特异性合成一种D-丙氨酸衍生物，其氮原子被包含在一个3,4-二取代[1,2]噁唑烷-3-酮内。关键词：D-ala-D-ala替代物，环康纳林，同型拉维西汀，肽聚糖，三甲基铝。

  DOI：

  10.1139/v03-122
• 作为产物：
  描述：

  α-氨基-γ-丁内酯氢溴酸盐 、 苯乙酰氯 在 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 3.0h， 以95%的产率得到α-Phenylacetamido-γ-Butyrolactone
  参考文献：
  名称：

  Cyclic hydroxamates, especially multiply substituted [1,2]oxazinan-3-ones

  摘要：

  报道了将假定的N-酰-D-阿拉-D-阿拉替代物的合成途径，从将4、5和6元环内酯转化为5、6和7元环氢氧化物开始。合成的关键步骤是ω-氨氧酯的三甲基铝促进的环化反应。7元环氢氧化物以椅式构象结晶。将反应序列扩展到同型丝氨酸或同型丝氨酸内酯会导致环康纳林和N-酰化环康纳林的形成。环康纳林的4-苯乙酰氨基衍生物以船式构象结晶。在环康纳林的4-酰氨基环康纳林的环氮上附加2-羧基丙基取代基，可以通过将无环氨氧酯前体与苄乳酸三甲酯的三氟甲磺酸酯偶联，或在环化之后，通过与三氟甲基丙酸叔丁酯在氟化钾-氧化铝存在下偶联，然后在每种情况下去除保护基来实现。通过4-苯乙酰氨基环康纳林与苄基2-氧戊二酸酯在异亚胺存在下反应，然后进行氢解，合成了抗生素拉维西汀的六元同系物。从甲基2,4-二溴-2,4-二去氧-L-赤葡萄糖酸甲酯开始，该物质可以从抗坏血酸中经过两步合成，这些反应序列已被应用于立体特异性合成一种D-丙氨酸衍生物，其氮原子被包含在一个3,4-二取代[1,2]噁唑烷-3-酮内。关键词：D-ala-D-ala替代物，环康纳林，同型拉维西汀，肽聚糖，三甲基铝。

  DOI：

  10.1139/v03-122

文献信息

• Method for synthesizing oxazinones
  申请人：——

  公开号：US20030232820A1

  公开（公告）日：2003-12-18

  New methods and intermediates are discussed for the stereospecific synthesis of oxazinone compounds.

  讨论了用于氧杂环酮化合物立体特异合成的新方法和中间体。
• Compound Combinations for Attenuation of Bacterial Virulence
  申请人：WISCONSIN ALUMNI RESEARCH FOUNDATION

  公开号：US20170231962A1

  公开（公告）日：2017-08-17

  Methods for modulating quorum sensing in certain Gram-negative bacteria having multiple QS systems including Las, Rhl, and Pqs with associated receptors (LasR, RhlR and PqsR) which are modulated by small molecule modulators, particularly non-native modulators. Certain combinations of modulators of Las, Rhl and Pqs exhibit improved inhibition of virulence in comparison to the respective individual modulators. In particular, certain combinations of modulators exhibit improved inhibition in nutritionally depleted environments. More specifically, certain combinations of modulators exhibit improved inhibition in environments depleted in phosphate and/or environments depleted in iron. Nutrient depleted environments can mimic environments associated with bacterial infection in humans and non-human animals. The methods are useful in particular for modulating QS in Pseudomonas and Buckholderia.

  在某些具有多个QS系统的革兰氏阴性细菌中，包括具有相关受体（LasR、RhlR和PqsR）的Las、Rhl和Pqs的调控方法，这些受体受小分子调节剂（尤其是非天然调节剂）的调节。Las、Rhl和Pqs的某些调节剂组合相比于各自的单个调节剂表现出对毒力的改善抑制。特别是，某些调节剂组合在营养匮乏环境中表现出改善的抑制作用。更具体地说，某些调节剂组合在缺乏磷酸盐和/或缺乏铁的环境中表现出改善的抑制作用。营养匮乏环境可以模拟与人类和非人类动物细菌感染相关的环境。这些方法特别适用于调节假单胞菌和布氏杆菌中的QS。
• Chemo-enzymatic synthesis of the azasugars 1,4-dideoxyallonojirimycin and 1,4-dideoxymannojirimycin
  作者：Mallam Venkataiah、Gowrisankar Reddipalli、Lakshmi Swarnalatha Jasti、Nitin W. Fadnavis

  DOI：10.1016/j.tetasy.2011.10.015

  日期：2011.11

  The enzymatic resolution of the N-phenylacetyl derivative of racemic homoserine lactone with penicillin G acylase immobilized on Eupergit C gave (R)-(+)-alpha-amino-gamma-butyrolactone and (S)-(-)-alpha-N-phenylacetamido-gamma-butyrolactone in high enantiomeric purity (ee >99%) and 46-47% yields for each enantiomer. The enantiomers were converted into azasugars 1,4-dideoxyallonojirimycin and 1,4-dideoxymannojirimycin using Wittig olefination, catalytic ring-closing metathesis (RCM), and stereoselective dihydroxylation with OsO4 in 29% overall yield over 11 high yielding steps. Enzyme inhibition studies showed that 1,4-dideoxyallonojirimycin is a better beta-glucosidase inhibitor (IC50 32.4 mu M toward beta-glucosidase from almonds) and a better beta-galactosidase inhibitor (IC50 5.9 mM for beta-galactosidase from Aspergillus oryzae) than 1,4-dideoxymannojirimycin (IC50 2.86 mM and 12.5 mM for beta-glucosidase and beta-galactosidase, respectively). (C) 2011 Elsevier Ltd. All rights reserved.
• Modulation of Bacterial Quorum Sensing with Synthetic Ligands
  申请人：Blackwell Helen E.

  公开号：US20080312319A1

  公开（公告）日：2008-12-18

  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.
• Modulation of Bacterial Quorum Sensing With Synthetic Ligands
  申请人：Blackwell Helen E.

  公开号：US20110212860A1

  公开（公告）日：2011-09-01

  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.