N-methyl-3,5-dimethylpyrrolidin-2-one | 1447173-72-9

• 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: N-methyl-3,5-dimethylpyrrolidin-2-one
• 英文别名: 1,3,5-trimethylpyrrolidin-2-one；(3R,5R)-1,3,5-Trimethylpyrrolidin-2-one
• CAS: 1447173-72-9
• 化学式: C₇H₁₃NO
• 分子量: 127.186
• InChiKey: ZBLCKMSVDNMPLC-PHDIDXHHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.8
• 重原子数：
  9
• 可旋转键数：
  0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.86
• 拓扑面积：
  20.3
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为产物：
  描述：

  L-焦谷氨酸乙酯 在 锂硼氢 、 三正丁基氢锡 、 sodium hydride 、 对甲苯磺酸 、 三乙胺 、 sodium iodide 、 lithium diisopropyl amide 作用下， 以 四氢呋喃 、 甲醇 、 乙二醇二甲醚 、 甲苯 为溶剂， 生成 N-methyl-3,5-dimethylpyrrolidin-2-one
  参考文献：
  名称：

  Anti-Beckwith stereoselectivity in amidyl radical cyclisations: Bu3SnH-mediated 5-exo-trig acyl mode cyclisation of 2-substituted pent-4-enamide radicals

  摘要：

  2-Substituted amidyl radicals derived from 8a-d and 9a-d undergo acyl mode 5-exo-trig cyclisation to give 3,5-trans pyrrolidinones 11a-d and 14a-d as the major products in low diastereoselectivity (de = 9-36%). The steric nature of the nitrogen substituent attached to the amidyl radical does not have a significant effect on selectivity. The stereochemical outcome is opposite to that expected based upon applying the Beckwith rule. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2013.05.109

文献信息

• Asymmetric Synthesis of <i>N</i> ‐Substituted γ‐Amino Esters and γ‐Lactams Containing α,γ‐Stereogenic Centers via a Stereoselective Enzymatic Cascade
  作者：Ming Li、Yunfeng Cui、Zefei Xu、Xi Chen、Jinhui Feng、Min Wang、Peiyuan Yao、Qiaqing Wu、Dunming Zhu

  DOI：10.1002/adsc.202100953

  日期：2022.1.18

  esters and γ-lactams containing α,γ-stereogenic centers are widely used as chiral intermediates in various bioactive compounds, while their efficient synthesis remains a challenge. Herein, an enzymatic cascade reaction involving an ene reductase (ERED) and an imine reductase (IRED) for accessing to α,γ-stereospecific γ-amino esters and γ-lactams from α,β-unsaturated γ-ketoesters has been developed

  含有α，γ-立体中心的γ-氨基酯和γ-内酰胺被广泛用作各种生物活性化合物的手性中间体，而它们的有效合成仍然是一个挑战。本文开发了一种涉及烯还原酶 (ERED) 和亚胺还原酶 (IRED) 的酶级联反应，用于从 α,β-不饱和 γ-酮酯中获得 α,γ-立体特异性 γ-氨基酯和 γ-内酰胺。已鉴定出 21 个 ERED 和 13 个 IRED，分别对各种 α,β-不饱和 γ-酮酯和相应的手性 γ-酮酯具有高活性和立体选择性。通过采用合适的 ERED 和 IRED，(1 S ,3 S )、(1 S ,3 R )、(1 R ,3 S ) 和 (1 R,3 R ) 3-(环丙基氨基) 环己烷-1-羧酸甲酯的立体异构体作为单一立体异构体以 63–72% 的收率获得, (3 R ,5 R )- 和 (3 R ,5 S )-1 -环丙基-3,5-二甲基吡咯烷-2-一和1-环丙基-3,5-二丙基吡咯烷-2-
• Anti-Beckwith stereoselectivity in amidyl radical cyclisations: Bu3SnH-mediated 5-exo-trig acyl mode cyclisation of 2-substituted pent-4-enamide radicals
  作者：Andrew J. Clark、Robert P. Filik、Gerard H. Thomas、John Sherringham

  DOI：10.1016/j.tetlet.2013.05.109

  日期：2013.7

  2-Substituted amidyl radicals derived from 8a-d and 9a-d undergo acyl mode 5-exo-trig cyclisation to give 3,5-trans pyrrolidinones 11a-d and 14a-d as the major products in low diastereoselectivity (de = 9-36%). The steric nature of the nitrogen substituent attached to the amidyl radical does not have a significant effect on selectivity. The stereochemical outcome is opposite to that expected based upon applying the Beckwith rule. (C) 2013 Elsevier Ltd. All rights reserved.