(S)-4-acetoxy-1-benzyl-2,5-pyrrolidinedione | 129823-21-8

• 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)-4-acetoxy-1-benzyl-2,5-pyrrolidinedione
• 英文别名: (3S)-1-benzyl-3-acetatoxypyrrolidine-2,5-dione；(3S)-3-acetyloxy-1-benzyl-2,5-pyrrolidinedione；S-(-)-3-(Acetyloxy)-1-(phenylmethyl)-2,5-pyrrolidinedione；[(3S)-1-benzyl-2,5-dioxopyrrolidin-3-yl] acetate
• CAS: 129823-21-8
• 化学式: C₁₃H₁₃NO₄
• 分子量: 247.251
• InChiKey: BMIVTLPISDRDHK-NSHDSACASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.7
• 重原子数：
  18
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  63.7
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (S)-4-acetoxy-1-benzyl-2,5-pyrrolidinedione 在 lithium diisopropyl amide 作用下， 反应 42.5h， 生成 1-benzyl-5-ethoxy-4-hydroxy-3-(prop-2-ynyl)-2-pyrrolidinone
  参考文献：
  名称：

  Studies toward the Total Synthesis of the Oxindole Alkaloid Gelsedine:  An Efficient Allene-Terminated N-Acyliminium Ion Cyclization

  摘要：

  DOI：

  10.1021/jo971510n
• 作为产物：
  描述：

  3-acetoxy-1-benzyl-2,5-pyrrolidinedione 生成 (S)-4-acetoxy-1-benzyl-2,5-pyrrolidinedione
  参考文献：
  名称：

  (R)-1-苄基-3-羟基-2,5-吡咯烷二酮及其相关化合物的脂肪酶催化实际合成

  摘要：

  通过使用其乙酸酯 (2a) 的酶促水解，研究了制备 (R)-1-苄基-3-羟基-2,5-吡咯烷二酮 (1) 的实用方法。在这里检测的几种水解酶中，洋葱假单胞菌的脂肪酶 PS 的结果最好：在二恶烷和磷酸盐缓冲液 (pH 7) 的混合溶剂 (1:1 v/v) 中，水解以高对映选择性 (E > 3000）。1 的几种 3-烷酰基衍生物经过脂肪酶 PS 催化水解。烷酰基的链长不会显着影响反应速率或对映选择性。相比之下，1-苯甲酰基衍生物的水解缓慢进行，对映选择性低（E = 19）。

  DOI：

  10.1246/bcsj.69.207

文献信息

• [EN] COMPOUNDS INHIBITING LEUCINE-RICH REPEAT KINASE ENZYME ACTIVITY<br/>[FR] COMPOSÉS INHIBANT L'ACTIVITÉ ENZYMATIQUE DE LA KINASE À MOTIFS RÉPÉTÉS RICHES EN LEUCINE
  申请人：MERCK SHARP & DOHME

  公开号：WO2014137723A1

  公开（公告）日：2014-09-12

  The present invention is directed to indazole compounds which are potent inhibitors of LRRK2 kinase and useful in the treatment or prevention of diseases in which the LRRK2 kinase is involved, such as Parkinson's Disease. The invention is also directed to pharmaceutical compositions comprising these compounds and the use of these compounds and compositions in the prevention or treatment of such diseases in which LRRK-2 kinase is involved.

  本发明涉及吲唑类化合物，这些化合物是LRRK2激酶的有效抑制剂，并且在治疗或预防LRRK2激酶参与的疾病，如帕金森病中有用。该发明还涉及包含这些化合物的药物组合物，以及在预防或治疗LRRK-2激酶参与的这类疾病中使用这些化合物和组合物。
• [EN] COMPOUNDS INHIBITING LEUCINE-RICH REPEAT KINASE ENZYME ACTIVITY<br/>[FR] COMPOSÉS INHIBANT L'ACTIVITÉ ENZYMATIQUE DE LA KINASE À SÉQUENCE RÉPÉTÉE RICHE EN LEUCINE
  申请人：MERCK SHARP & DOHME

  公开号：WO2014134774A1

  公开（公告）日：2014-09-12

  Disclosed are indazole compounds which are potent inhibitors of LRRK2 kinase and useful in the treatment or prevention of diseases in which LRRK2 kinase is involved. Also disclosed are pharmaceutical compositions in the prevention or treatment of such diseases in which LRRK2 kinase is involved.

  揭示了一种indazole化合物，它们是LRRK2激酶的有效抑制剂，并且在涉及LRRK2激酶的疾病的治疗或预防中有用。还揭示了在涉及LRRK2激酶的这类疾病的预防或治疗中使用的药物组合物。
• Pharmaceutically useful furo[3,2-c]pyridines
  申请人：Glaxo Group Limited

  公开号：US05109008A1

  公开（公告）日：1992-04-28

  Compounds are disclosed of formula (I) ##STR1## wherein R.sub.1 represents hydrogen, unsubstituted or substituted C.sub.1-6 alkyl, halogen, --COR.sub.4 or --CO.sub.2 R.sub.4 (where R.sub.4 represents hydrogen or unsubstituted or substituted C.sub.1-6 alkyl); R.sub.2 and R.sub.3 are the same or different and are C.sub.1-6 alkyl or C.sub.3-6 alkenyl; or --NR.sub.2 R.sub.3 forms a 5-membered (optionally containing an oxygen atom adjacent to the nitrogen) or a 6-membered ring, which ring optionally contains one unit of unsaturation and which is unsubstituted or substituted by hydroxy, C.sub.1-6 acyloxy, oxo, optionally substituted methylidene, --COR.sub.5 (where R.sub.5 represents C.sub.1-6 alkyl, OR.sub.6 or --NHR.sub.6, and R.sub.6 represents hydrogen, C.sub.1-6 alkyl, aryl or ar(C.sub.1-6)alkyl) or said ring is substituted by .dbd.NOR.sub.7 (where R.sub.7 represents C.sub.1-6 alkyl); Z represents --O-- or --S--; X represents a direct bond, --CH.sub.2 -- or --CH.sub.2 O--; Ar represents a substituted phenyl moiety; and pharmaceutically acceptable salts thereof. The compounds are indicated as useful in the treatment of pain and cerebral ischaemia. Processes and intermediates for their preparation and pharmaceutical compositions containing them are also disclosed.

  披露了公式(I)的化合物##STR1##，其中R1代表氢，未取代或取代的C1-6烷基，卤素，--COR4或--CO2R4（其中R4代表氢或未取代或取代的C1-6烷基）；R2和R3相同或不同，为C1-6烷基或C3-6烯基；或--NR2R3形成一个5元环（可选地含有与氮原子相邻的一个氧原子）或一个6元环，该环可选地含有一个不饱和单元，并且该环未取代或取代有羟基，C1-6酰氧基，氧亚基，可选地取代的亚甲基，--COR5（其中R5代表C1-6烷基，OR6或--NHR6，R6代表氢，C1-6烷基，芳基或芳(C1-6)烷基）或该环被.dbd.NOR7取代（其中R7代表C1-6烷基）；Z代表--O--或--S--；X代表直接键，--CH2--或--CH2O--;Ar代表取代的苯基部分；以及它们的药物可接受的盐。这些化合物被指示用于治疗疼痛和脑缺血。还披露了它们的制备过程和中间体以及含有它们的药物组合物。
• Studies towards the synthesis of (+)-ptilomycalin A; Stereoselective N-acyliminium ion coupling reactions to enantiopure C-2 substituted lactams
  作者：Saskia Louwrier、Martin Ostendorf、Arnoud Boom、Henk Hiemstra、W. Nico Speckamp

  DOI：10.1016/0040-4020(95)01085-8

  日期：1996.2

  Highly stereoselective N-acyliminium ion coupling reactions of β-ketoester derived silyl enol ethers with enantiopure lactams derived from (S)-malic acid are reported. This reaction type is applied in the synthesis of the enantiopure C-2 substituted lactam 27, a plausible intermediate in a projected synthesis of ptilomycalin A.

  报道了β-酮酸酯衍生的甲硅烷基烯醇醚与衍生自（S）-苹果酸的对映体纯内酰胺的高度立体选择性的N-酰亚胺离子偶联反应。这种反应类型适用于对映体C-2取代的内酰胺27的合成，内酰胺27是拟定的Ptilomycalin A合成中可能的中间体。
• Lewis-acid catalyzed N-acyliminium ion cyclodimerization: synthesis of symmetrical 1,4-dioxanes
  作者：Bakhat Ali、Julio Zukerman-Schpector、Fernando P. Ferreira、Anwar Shamim、Daniel C. Pimenta、Hélio A. Stefani

  DOI：10.1016/j.tetlet.2015.01.059

  日期：2015.2

  The cyclodimerization reaction of N-substituted-5-hydroxy-pyrrolydinones promoted by BF3·Et2O and HCl to obtain symmetrical 1,4-dioxane derivatives was achieved in moderate to good yields, mild conditions, and short reaction times. These transformations render a promising alternative route that provides access to diverse 1,4-dioxane derivatives with a wide structural diversity.

  以中等至良好的收率，温和的条件和较短的反应时间，实现了由BF 3 ·Et 2 O和HCl促进的N-取代的5-羟基-吡咯烷酮类的环二聚反应，以得到对称的1,4-二恶烷衍生物。这些转变提供了一种有前途的替代途径，该途径提供了获得具有广泛结构多样性的多种1,4-二恶烷衍生物的途径。