(S)-(-)-3-methyl-2-pyrrolidinone | 55709-17-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯烷类
• 英文名称: (S)-(-)-3-methyl-2-pyrrolidinone
• 英文别名: (S)-3-methylpyrrolidin-2-one；(3S)-3-methylpyrrolidin-2-one
• CAS: 55709-17-6
• 化学式: C₅H₉NO
• 分子量: 99.1326
• InChiKey: AOCWQPKHSMJWPL-BYPYZUCNSA-N

物化性质

• 沸点：
  70 °C(Press: 0.3 Torr)
• 密度：
  0.979±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.2
• 重原子数：
  7
• 可旋转键数：
  0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.8
• 拓扑面积：
  29.1
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  (S)-(-)-3-methyl-2-pyrrolidinone 在 4-二甲氨基吡啶 、 lithium hydroxide 作用下， 以 四氢呋喃 为溶剂， 反应 5.0h， 生成 (S)-4-((tert-butoxycarbonyl)amino)-2-methylbutanoic acid
  参考文献：
  名称：

  Asymmetric synthesis of 3-substituted pyrrolidones via α-alkylation of a chiral non-racemic γ-lactam

  摘要：

  3-Alkyl pyrrolidones 9 were synthesized in good yield and high diastereoselectivity by oc-alkylation of the new chiral non-racemic lactam 8 derived from (R)-(-)-phenylglycinol. After debenzylation and introduction of an electron-withdrawing group, 3-methylpyrrolidone 10 is easily hydrolyzed in a basic medium to produce gamma-aminobutyric acid (GABA) analogue 13. (C) 1998 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(98)00024-x
• 作为产物：
  描述：

  (S)-2-methyl-4-phthalimido-butyric acid 以69%的产率得到
  参考文献：
  名称：

  RINGDAHL B.; DAHLBOM R., ACTA PHARM. SUEC., 1978, 15, NO 4, 255-263

  摘要：

  DOI：

文献信息

• Enantioselective Synthesis of 2-Substituted 5-, 6- and 7-Membered Lactams via α-Alkylation of Their Chiral N-Dialkylamino Derivatives
  作者：Dieter Enders、Robert Gröbner、Gerhard Raabe、Jan Runsink

  DOI：10.1055/s-1996-4443

  日期：1996.8

  2-Alkyl-substituted lactams 4 were synthesized in good overall yields and high enantiomeric purities (ee =71-99%) by α-alkylation of chiral N-(dialkylamino)lactams 2 and subsequent reductive N-N bond cleavage of the resulting lactams 3 with lithium in liquid ammonia. The lactams 2, in turn, were prepared in good yields by cyclization of ω-chloroalkanohydrazides 1 with sodium hydride. Acidic hydrolysis of lactams 4 leads to γ-aminobutanoic acid (GABA) derivatives 5 (ee ≥ 99%). The absolute configuration was determined by polarimetry and an X-ray structure analysis of (S,S)-3e’.

  通过手性N-（二烷基氨基）内酰胺2的α-烷基化反应，随后在液氨中使用锂进行所得内酰胺3的还原性N-N键断裂，合成了具有良好总收率和高对映体纯度（ee = 71-99%）的2-烷基取代内酰胺4。这些内酰胺2是通过将β-氯代烷基酰肼1与氢化钠环合反应制备的，收率良好。内酰胺4的酸性水解得到γ-氨基丁酸（GABA）衍生物5（ee ≥ 99%）。绝对构型通过旋光仪测定和（S，S）-3e’的X射线结构分析确定。
• Optical Resolution of Cyclic Amides by Inclusion in Dehydrocholic Acid
  作者：Olga Bortolini、Marco Fogagnolo、Giancarlo Fantin、Alessandro Medici

  DOI：10.1246/cl.2003.206

  日期：2003.3

  Dehydrocholic acid serves as an effective chiral host for the resolution of several five-, six-, and seven-membered cyclic amides by inclusion.

  脱氢胆酸可作为有效的手性主体，通过包合拆分几种五元、六元和七元环酰胺。
• Separation of (S)-(−)-3-Methyl-2-pyrrolidinone as an Inclusion Complex with (R)-(+)-4,4′,6,6′-Tetrachloro-2,2′-bis(hydroxydiphenylmethyl)-1,1′-biphenyl Host and its X-ray Structural Study
  作者：Tanya le Roex、Luigi R. Nassimbeni、Fumio Toda

  DOI：10.1007/s10870-007-9312-8

  日期：2008.1

  By inclusion complexation with the chiral host compound (R)-(+)-4,4′,6,6′-tetrachloro-2,2′-bis(hydroxydiphenylmethyl)-1,1′-biphenyl, racemic 3-methyl-2-pyrrolidinone was resolved and its (S)-(−)-enantiomer was isolated as a 1:1 inclusion complex, which crystallises in the orthorhombic crystal system in the space group P212121 (a = 14.1163(2) Å, b = 14.7140(3) Å, c = 17.2025(3) Å). By the inclusion complexation, the keto–enol equilibrium of the guest was frozen and the keto-form was isolated in a pure form. By X-ray structural study of the complex, the guest molecule included was elucidated to be the keto-form and its absolute configuration was determined to be (S). By inclusion complexation with (R)-(+)-4,4′,6,6′-tetrachloro-2,2′-bis (hydroxydiphenylmethyl)-biphenyl, racemic 3-methyl-2-pyrrolidinone was resolved and its (S)-(−)-enantiomer isolated and in addition the keto–enol equilibrium of the guest was frozen and the keto-form isolated.

  通过与手性主体化合物(R)-(+)-4,4',6,6'-四氯-2,2'-双(羟基二苯基甲基)-1,1'-联苯的包合络合，得到外消旋3-甲基- 2-吡咯烷酮被解析，其 (S)-(−)-对映体被分离为 1:1 包合物，在空间群 P212121 的斜方晶系中结晶 (a = 14.1163(2) Å，b = 14.7140 (3) Å, c = 17.2025(3) Å)。通过包合络合，客体的酮-烯醇平衡被冻结，并且酮形式以纯形式分离。通过对该配合物的X射线结构研究，确定所包含的客体分子为酮型，其绝对构型确定为(S)。通过与(R)-(+)-4,4',6,6'-四氯-2,2'-双(羟基二苯基甲基)-联苯的包合络合，拆分出外消旋3-甲基-2-吡咯烷酮，并得到其(S )-(−)-对映异构体被分离，此外客体的酮-烯醇平衡被冻结并分离出酮形式。
• Asymmetric synthesis of 3-substituted pyrrolidones via α-alkylation of a chiral non-racemic γ-lactam
  作者：Isabelle Baussanne、Catherine Travers、Jacques Royer

  DOI：10.1016/s0957-4166(98)00024-x

  日期：1998.3

  3-Alkyl pyrrolidones 9 were synthesized in good yield and high diastereoselectivity by oc-alkylation of the new chiral non-racemic lactam 8 derived from (R)-(-)-phenylglycinol. After debenzylation and introduction of an electron-withdrawing group, 3-methylpyrrolidone 10 is easily hydrolyzed in a basic medium to produce gamma-aminobutyric acid (GABA) analogue 13. (C) 1998 Elsevier Science Ltd. All rights reserved.
• RINGDAHL B.; DAHLBOM R., ACTA PHARM. SUEC., 1978, 15, NO 4, 255-263
  作者：RINGDAHL B.、 DAHLBOM R.

  DOI：——

  日期：——