(3S)-1-benzyl-3-acetatoxypyrrolidine | 124445-27-8

• 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: (3S)-1-benzyl-3-acetatoxypyrrolidine
• 英文别名: (S)-N-benzyl-3-pyrrolidinyl acetate；(S)-3-acetoxy-1-benzylpyrrolidine；(3S)-1-benzyl-3-acetoxypyrrolidine；[(3S)-1-benzylpyrrolidin-3-yl] acetate
• CAS: 124445-27-8
• 化学式: C₁₃H₁₇NO₂
• 分子量: 219.283
• InChiKey: WAZGGSCOYCPXGS-ZDUSSCGKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  16
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.46
• 拓扑面积：
  29.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (3S)-1-benzyl-3-acetatoxypyrrolidine 在 palladium dihydroxide 、 氢气 作用下， 以 甲醇 为溶剂， 生成 (S)-(pyrrolidin-3-yl) acetate
  参考文献：
  名称：

  EP1741703

  摘要：

  公开号：
• 作为产物：
  描述：

  苄胺 在 吡啶 、 lithium aluminium tetrahydride 、 sodium hydroxide 作用下， 以 四氢呋喃 、 甲醇 、 水 为溶剂， 反应 23.0h， 生成 (3S)-1-benzyl-3-acetatoxypyrrolidine
  参考文献：
  名称：

  3-Hydroxypyrrolidine and (3,4)-dihydroxypyrrolidine derivatives: Inhibition of rat intestinal α-glucosidase

  摘要：

  Thirteen pyrrolidine-based iminosugar derivatives have been synthesized and evaluated for inhibition of a-glucosidase from rat intestine. The compounds studied were the non-hydroxy, mono-hydroxy and dihydroxypyrrolidines. All the compounds were N-benzylated apart from one. Four of the compounds had a carbonyl group in the 2,5-position of the pyrrolidine ring. The most promising iminosugar was the trans-3,4-dihydroxypyrrolidine 5 giving an IC50 of 2.97 +/- 0.046 and a K-I of 1.18 mM. Kinetic studies showed that the inhibition was of the mixed type, but predominantly competitive for all the compounds tested. Toxicological assay results showed that the compounds have low toxicity. Docking studies showed that all the compounds occupy the same region as the DNJ inhibitor on the enzyme binding site with the most active compounds establishing similar interactions with key residues. Our studies suggest that a rotation of similar to 90 degrees of some compounds inside the binding pocket is responsible for the complete loss of inhibitory activity.Despite the fact that activity was found only in the mM range, these compounds have served as simple molecular tools for probing the structural features of the enzyme, so that inhibition can be improved in further studies. (C) 2014 Elsevier Inc. All rights reserved.

  DOI：

  10.1016/j.bioorg.2014.04.007

文献信息

• Lipase-Catalyzed Practical Synthesis of (<i>R</i>)-1-Benzyl-3-hydroxy-2,5-pyrrolidinedione and Its Related Compounds
  作者：Hiroshi Tomori、Kuniko Shibutani、Katsuyuki Ogura

  DOI：10.1246/bcsj.69.207

  日期：1996.1

  investigated by the use of the enzymatic hydrolysis of its acetate (2a). Among several hydrolases examined here, lipase PS from Pseudomonas cepaciagave the best result: In a mixed solvent (1 : 1 v/v) of dioxane and a phosphate buffer (pH 7), the hydrolysis took place smoothly with a high enantioselectivity (E > 3000). Several 3-alkanoyl derivatives of 1 were subjected to the lipase PS-catalyzed hydrolysis

  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）。
• Substituted 3-Amino-4-hydroxy pyrrolidines compounds, their preparation and use as medicaments
  申请人：Laboratorios del Dr. Esteve S.A.

  公开号：EP1849781A1

  公开（公告）日：2007-10-31

  The present invention relates to substituted pyrrolidine compounds of general formula (I), methods for their preparation, medicaments comprising these compounds as well as their use for the preparation of a medicament for the treatment of humans and animal.

  本发明涉及通式（I）的取代吡咯烷化合物，其制备方法，包含这些化合物的药物以及它们在制备用于治疗人类和动物的药物中的应用。
• Enzymatic Optical Resolution of<i>N</i>-Benzyl-3-pyrrolidinol
  作者：Akira Horiguchi、Ken-ichi Mochida

  DOI：10.1271/bbb.59.1287

  日期：1995.1

  The enzymatic optical resolution of racemic N-benzyl-3-pyrrolidinol (2) was investigated. It was found that only (R)-2 was acetylated by the lipase Amano P in yields of 50% and 100%e.e. Remaining (S)-alcohol 2 could be chemically inverted to (R)-acetate 3. A continuous reaction in a column reactor could be also applied to this optical resolution. After concentrating the eluted solution, the residue was subjected to the inversion reaction to provide (R)-acetate 3 in an 83% yield and 91%e.e. from the racemate.

  研究了外消旋 N-苄基-3-吡咯烷醇（2）的酶光学分解。研究发现，只有(R)-2 能被脂肪酶 Amano P 乙酰化，乙酰化率分别为 50%和 100%，即剩余的(S)-醇 2 可以通过化学反应转化为(R)-乙酸酯 3。柱式反应器中的连续反应也可用于这种光学分解。浓缩洗脱溶液后，残留物进行反转反应，得到(R)-乙酸酯 3，收率为 83%，外消旋体的反应效率为 91%e.e.。
• Pyridone derivative
  申请人：Otake Norikazu

  公开号：US20070208046A1

  公开（公告）日：2007-09-06

  The invention provides pyridone derivatives represented by a general formula (I) [in the formula, R 1 and R 2 may be same or different and stands for H, etc., or R 1 and R 2 may form an aliphatic nitrogen-containing heterocyclic group together with the N to which they bind; X 1 -X 3 may be same or different and stand for methine or N, provided not all of them simultaneously stand for nitrogen; X 4 -X 7 may be same or different and stand for methine or N, provided that three or more of them do not simultaneously stand for N; Y 1 and Y 3 may be same or different and stand for single bond, —O—, —NR—, —S—, etc; Y 2 stands for lower alkylene, etc.; R stands for H, etc., L stands for methylene; Z 1 and Z 2 may be same or different and stand for single bond or lower alkylene; or R 1 , L and Z 2 may form an aliphatic nitrogen-containing heterocyclic group with the N to which R 1 binds; and Ar stands for aromatic carbocyclic group, etc.].

  该发明提供了由通式（I）表示的吡啶酮衍生物[在公式中，R1和R2可能相同或不同，代表H等，或者R1和R2可能与它们结合的N一起形成一个脂肪族含氮杂环基团；X1-X3可能相同或不同，代表亚甲或N，但不能同时都代表氮；X4-X7可能相同或不同，代表亚甲或N，但不能同时有三个或更多同时代表N；Y1和Y3可能相同或不同，代表单键，-O-，-NR-，-S-等；Y2代表较低的烷基等；R代表H等，L代表亚甲基；Z1和Z2可能相同或不同，代表单键或较低的烷基；或者R1、L和Z2可能与R1结合的N一起形成一个脂肪族含氮杂环基团；Ar代表芳香族碳环基团等]。
• PYRIDONE DERIVATIVE
  申请人：BANYU PHARMACEUTICAL CO., LTD.

  公开号：EP1741703A1

  公开（公告）日：2007-01-10

  The invention provides pyridone derivatives represented by a general formula (I) [in the formula, R1 and R2 may be same or different and stands for H, etc., or R1 and R2 may form an aliphatic nitrogen-containing heterocyclic group together with the N to which they bind; X1-X3 may be same or different and stand for methine or N, provided not all of them simultaneously stand for nitrogen; X4-X7 may be same or different and stand for methine or N, provided that three or more of them do not simultaneously stand for N; Y1 and Y3 may be same or different and stand for single bond, -0-, -NR-, -S-, etc ; Y2 stands for lower lkylene, etc.; R stands for H, etc., L stands for methylene; Z1 and Z2 may be same or different and stand for single bond or lower alkylene; or R1, L and Z2 may form an aliphatic nitrogen-containing heterocyclic group with the N to which R1 binds; and Ar stands for aromatic carbocyclic group, etc.].

  本发明提供了通式 (I) 所代表的吡啶酮衍生物 [式中，R1 和 R2 可以相同或不同，代表 H 等、或 R1 和 R2 可与它们结合的 N 一起形成一个脂族含氮杂环基团；X1-X3 可相同或不同，代表甲烷或 N，条件是它们中的三个或更多不同时代表氮；X4-X7 可相同或不同，代表甲烷或 N，条件是它们中的三个或更多不同时代表 N；Y1 和 Y3 可相同或不同，代表单键、-0-、-NR-、-S-等；Y2 代表低级亚烷基等。R 代表 H 等、L 代表亚甲基；Z1 和 Z2 可相同或不同，代表单键或低级亚烷基；或 R1、L 和 Z2 可与 R1 结合的 N 形成脂肪族含氮杂环基团；Ar 代表芳香族碳环基团等]。