(S)-3-benzoyloxy-γ-butyrolactone | 207985-74-8

• 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)-3-benzoyloxy-γ-butyrolactone
• 英文别名: (S)-5-oxotetrahydrofuran-3-yl benzoate；(S)-β-benzoyloxy-γ-butyrolactone；(S)-beta-Benzoyloxy-gamma-butyrolactone；[(3S)-5-oxooxolan-3-yl] benzoate
• CAS: 207985-74-8
• 化学式: C₁₁H₁₀O₄
• 分子量: 206.198
• InChiKey: VLDYBOFCEJPWOJ-VIFPVBQESA-N

物化性质

• 熔点：
  73-74 °C
• 沸点：
  377.8±35.0 °C(Predicted)
• 密度：
  1.28±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  15
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  52.6
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (S)-3-benzoyloxy-γ-butyrolactone 在 4-二甲氨基吡啶 、 diisopropyl aluminum hydride 作用下， 以 四氢呋喃 、 三乙胺 、 甲苯 为溶剂， 反应 3.0h， 生成 (S)-α-O-acetyl-3-benzoyloxy-4-hydroxybutanal
  参考文献：
  名称：

  具有腺嘌呤碱基部分的3'- O-膦酰基甲基核苷的合成

  摘要：

  已经开发了用于从β-羟基-γ-丁内酯合成2'-脱氧苏糖膦酸酯核苷和从二羟基二氢呋喃-1-酮中合成2'-叠氮赤藓糖膦酸酯核苷的合成方案。另外，从受保护的α-d-半呋喃呋喃糖开始，合成了几种α-1-阿拉伯呋喃糖膦酸酯核苷。不幸的是，没有一种合成的化合物在HIV-1检测中显示出活性。使用HIV-1逆转录酶评估了其中一种化合物（锁定的膦酸酯核苷）（作为二磷酸酯）的潜力，将其掺入DNA中。

  DOI：

  10.1016/j.tet.2007.01.032
• 作为产物：
  描述：

  (S)-β-benzoyloxy-γ-succinic-anhydride 在 zinc(II) tetrahydroborate 、 盐酸 作用下， 以 四氢呋喃 为溶剂， 反应 4.5h， 以88%的产率得到(S)-3-benzoyloxy-γ-butyrolactone
  参考文献：
  名称：

  Beta-substituted-gamma-butyrolactones and a process for preparation thereof

  摘要：

  本发明涉及一种制备(S)-或(R)-β-取代-γ-丁内酯或其混合物的过程。将β-取代-γ-琥珀酸酐通过锌硼氢化物在四氢呋喃、二氯甲烷和乙酸乙酯中选择的相容溶剂中转化为相应的β-取代-γ-丁内酯。获得的β-取代-γ-丁内酯晶体形式有用于制药、农药、香料和香精的生产。还公开了新型β-取代-γ-丁内酯。

  公开号：

  EP1398312A1

文献信息

• Organocatalytic asymmetric oxy-Michael addition to a γ-hydroxy-α,β-unsaturated thioester via hemiacetal intermediates
  作者：Takaaki Okamura、Keisuke Asano、Seijiro Matsubara

  DOI：10.1039/c2cc31602a

  日期：——

  We report an asymmetric oxy-Michael addition to a γ-hydroxy-α,β-unsaturated thioester via hemiacetal intermediates in the presence of Cinchona-alkaloid-thiourea-based bifunctional organocatalysts. This method provides a novel enantioselective route to β-hydroxy carboxyl compounds, which in turn can be used to synthesize valuable chiral building blocks.

  我们报道了一种通过金鸡纳生物碱硫脲基双功能有机催化剂存在下的半缩醛中间体，对γ-羟基-α,β-不饱和硫酯进行不对称氧迈克尔加成的反应。该方法为合成β-羟基羧酸化合物提供了一条新颖的手性选择性途径，而这些化合物又可用于合成有价值的手性构建基块。
• Beta-substituted-gamma-butyrolactones and a process for preparation thereof
  申请人：Uh, Hong-Sun

  公开号：EP1398312A1

  公开（公告）日：2004-03-17

  The present invention is related to a process for the preparation of (S)- or (R)-β-substituted-γ-butyrolactones or a racemic mixture thereof. β-substituted-γ-succinic anhydrides are converted by zinc borohydride in a compatible solvent selected from tetrahydrofuran, methylene chloride, and ethyl acetate to the corresponding β-substituted-γ-butyrolactones. The β-substituted-γ-butyrolactones obtainable in chrystallin form are useful in the production of pharmaceuticals, agrochemicals, flavors and fragrances. Also disclosed are novel β-substituted-γ-butyrolactones.

  本发明涉及一种制备(S)-或(R)-β-取代-γ-丁内酯或其混合物的过程。将β-取代-γ-琥珀酸酐通过锌硼氢化物在四氢呋喃、二氯甲烷和乙酸乙酯中选择的相容溶剂中转化为相应的β-取代-γ-丁内酯。获得的β-取代-γ-丁内酯晶体形式有用于制药、农药、香料和香精的生产。还公开了新型β-取代-γ-丁内酯。
• Phosponate nucleosides useful as active ingredients in pharmaceutical compositions for the treatment of viral infections, and intermediates for their production
  申请人：Herdewijn Piet

  公开号：US20070185062A1

  公开（公告）日：2007-08-09

  The present invention relates to novel phosponate nucleosides, more specifically to novel phosponalkoxy substituted nucleosides. The invention further relates to compounds having HIV (Human Immunodeficiency Virus) replication inhibiting properties and to compounds having antiviral activities with respect to other viruses. The invention also relates to methods for preparation of all such compounds and pharmaceutical compositions comprising them. The invention further relates to the use of said compounds as a medicine and in the manufacture of a medicament useful for the treatment of subjects suffering from HIV infection, as well as for treatment of other viral, retroviral or lentiviral infections and to the treatment of animals suffering from FIV, viral, retroviral or lentiviral infections.

  本发明涉及新型磷酸酯核苷，更具体地涉及新型磷酸酯烷氧基取代核苷。本发明还涉及具有抑制HIV（人类免疫缺陷病毒）复制作用的化合物，以及具有抗其他病毒活性的化合物。本发明还涉及制备所有这些化合物的方法和包含它们的制药组合物。本发明还涉及将所述化合物用作药物以及制造有用于治疗HIV感染患者的药物，以及用于治疗其他病毒、逆转录病毒或慢病毒感染和治疗患有FIV、病毒、逆转录病毒或慢病毒感染的动物的药物的用途。
• Phosphonate nucleosides useful as active ingredients in pharmaceutical compositions for the treatment of viral infections, and intermediates for their production
  申请人：K.U.Leuven Research & Development

  公开号：US08076310B2

  公开（公告）日：2011-12-13

  Disclosed herein are novel phosphonate nucleosides and thiophosphonate nucleosides comprising a phosphonalkoxy-substituted or phosphonothioalkyl-substituted five-membered, saturated or unsaturated, oxygen-containing or sulfur-containing ring coupled to a heterocyclic nucleobase such as a pyrimidine or purine base. The invention further relates to compounds having HIV (Human Immunodeficiency Virus) replication inhibiting properties and to compounds having antiviral activities with respect to other viruses. The invention also relates to methods for preparation of all such compounds and pharmaceutical compositions comprising them. The invention further relates to the use of said compounds as a medicine and in the manufacture of a medicament useful for the treatment of subjects suffering from HIV infection, as well as for treatment of other viral, retroviral or lentiviral infections and to the treatment of animals suffering from FIV, viral, retroviral or lentiviral infections.

  本文公开了一种新型磷酸酯核苷和硫代磷酸酯核苷，其中包括一个磷酸烷氧基取代或磷酸硫烷基取代的五元饱和或不饱和含氧或含硫环与嘌呤或嘧啶碱基等杂环核苷碱基相结合。该发明还涉及具有HIV（人类免疫缺陷病毒）复制抑制性质的化合物，以及具有抗其他病毒活性的化合物。该发明还涉及制备所有这些化合物的方法和包含它们的制药组合物。该发明还涉及将所述化合物用作药物以及用于制造用于治疗HIV感染患者以及用于治疗其他病毒、逆转录病毒或慢病毒感染的药物，并用于治疗患有FIV、病毒、逆转录病毒或慢病毒感染的动物。
• PHOSPHONATE NUCLEOSIDES USEFUL AS ACTIVE INGREDIENTS IN PHARMACEUTICAL COMPOSITIONS FOR THE TREATMENT OF VIRAL INFECTIONS, AND INTERMEDIATES FOR THEIR PRODUCTION
  申请人：Herdewijn Piet

  公开号：US20120108531A1

  公开（公告）日：2012-05-03

  Disclosed herein are novel phosphonate nucleosides and thiophosphonate nucleosides comprising a phosphonalkoxy-substituted or phosphonothioalkyl-substituted five-membered, saturated or unsaturated, oxygen-containing or sulfur-containing ring coupled to a heterocyclic nucleobase such as a pyrimidine or purine base. The invention further relates to compounds having HIV (Human Immunodeficiency Virus) replication inhibiting properties and to compounds having antiviral activities with respect to other viruses. The invention also relates to methods for preparation of all such compounds and pharmaceutical compositions comprising them. The invention further relates to the use of said compounds as a medicine and in the manufacture of a medicament useful for the treatment of subjects suffering from HIV infection, as well as for treatment of other viral, retroviral or lentiviral infections and to the treatment of animals suffering from FIV, viral, retroviral or lentiviral infections.

  本文披露了一种新型磷酸酯核苷和硫代磷酸酯核苷，包括一个磷酸烷氧基取代或磷酸硫烷基取代的五元环，该环饱和或不饱和，含氧或含硫，与杂环核苷碱（如嘧啶或嘌呤碱基）结合。本发明还涉及具有HIV（人类免疫缺陷病毒）复制抑制性质的化合物，以及具有抗其他病毒活性的化合物。本发明还涉及制备所有这些化合物的方法和包含它们的药物组合物。本发明还涉及将所述化合物用作药物，并制造一种有用于治疗HIV感染患者以及治疗其他病毒、逆转录病毒或慢病毒感染和治疗患有FIV、病毒、逆转录病毒或慢病毒感染的动物的药物的药物。