tert-butyl (S)-2,5-dihydro-2-isobutyl-5-oxo-1H-pyrrole-1-carboxylate | 1188511-20-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯啉
• 英文名称: tert-butyl (S)-2,5-dihydro-2-isobutyl-5-oxo-1H-pyrrole-1-carboxylate
• 英文别名: tert-butyl (2S)-2-(2-methylpropyl)-5-oxo-2H-pyrrole-1-carboxylate
• CAS: 1188511-20-7
• 化学式: C₁₃H₂₁NO₃
• 分子量: 239.315
• InChiKey: HXCRRVHLZSQTHG-SNVBAGLBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  17
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.69
• 拓扑面积：
  46.6
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  tert-butyl (S)-2,5-dihydro-2-isobutyl-5-oxo-1H-pyrrole-1-carboxylate 在 四氧化锇 、 水 、 N-甲基吗啉氧化物 作用下， 以 丙酮 、 乙腈 为溶剂， 反应 32.0h， 以58%的产率得到tert-butyl (2S,3S,4S)-3,4-dihydroxy-2-isobutyl-5-oxo-1-pyrrolidinecarboxylate
  参考文献：
  名称：

  Concise Synthesis of PM-94128 and Y-05460M-A

  摘要：

  The enantioselective total synthesis of PM-94128, a potent cytotoxin of microbial origin, was accomplished by a concise nine-step sequence of reactions in 14% overall yield from N-Boc-L-leucine. The synthesis of Y-05460M-A, a one-carbon lower homologue of PM-94128, was also achieved from N-BOC-L-valine by the same approach, which enabled its stereochemical determination.

  DOI：

  10.1021/jo9014968
• 作为产物：
  描述：

  在 1,8-二氮杂双环[5.4.0]十一碳-7-烯 作用下， 以 二氯甲烷 为溶剂， 反应 0.67h， 以129 mg的产率得到tert-butyl (S)-2,5-dihydro-2-isobutyl-5-oxo-1H-pyrrole-1-carboxylate
  参考文献：
  名称：

  Concise Synthesis of PM-94128 and Y-05460M-A

  摘要：

  The enantioselective total synthesis of PM-94128, a potent cytotoxin of microbial origin, was accomplished by a concise nine-step sequence of reactions in 14% overall yield from N-Boc-L-leucine. The synthesis of Y-05460M-A, a one-carbon lower homologue of PM-94128, was also achieved from N-BOC-L-valine by the same approach, which enabled its stereochemical determination.

  DOI：

  10.1021/jo9014968

文献信息

• Cu‐Catalyzed Asymmetric Kinetic Boron Conjugate Addition of γ‐Substituted α,β‐Unsaturated γ‐Lactams
  作者：Liang Tang、Yicong Luo、Cheng Sheng、Fang Xie、Wanbin Zhang

  DOI：10.1002/anie.202304640

  日期：2023.6.19

  A Cu-catalyzed asymmetric kinetic boron conjugate addition of γ-substituted α,β-unsaturated γ-lactams followed by oxidation is reported with good results. This strategy provides an efficient access to valuable enantioenriched α,β-unsaturated γ-lactams bearing simple γ-alkyl or aryl substituents, which showed inhibitory activities against cisplatin-sensitive ovarian cancer cells A2780. A new Lewis acid

  据报道，Cu 催化的 γ-取代的 α,β-不饱和 γ-内酰胺的不对称动态硼共轭加成反应随后进行氧化，取得了良好的结果。该策略提供了一种有效获得有价值的对映体富集的α,β-不饱和γ-内酰胺的途径，该内酰胺带有简单的γ-烷基或芳基取代基，其对顺铂敏感的卵巢癌细胞A2780表现出抑制活性。提出了一种新的路易斯酸铜催化机理。
• HBTU Mediated Synthesis of α,β‐Unsaturated γ‐Lactams from <i>E</i>‐α,β‐Unsaturated γ‐Amino Acids
  作者：Manjeet Singh、Sachin A. Nalawade、DRGKoppalu. R. Puneeth Kumar、Kuruva Veeresh、Saikat Pahan、Sanjit Dey、Hosahudya N. Gopi

  DOI：10.1002/ejoc.202300682

  日期：2023.10.2

  The direct transformation of N-protected α,β-unsaturated γ-amino acids into corresponding α,β-unsaturated γ-lactams through in situ activation of carboxylic acid using the peptide coupling agent HBTU in the presence of base DIPEA is reported. The transformation involves the trans to cis isomerization of carbon-carbon double bonds.

  据报道，在碱 DIPEA 存在下，使用肽偶联剂 HBTU 通过原位活化羧酸，将 N-保护的 α,β-不饱和 γ-氨基酸直接转化为相应的 α,β-不饱和 γ-内酰胺。该转化涉及碳-碳双键的反式异构化为顺式异构化。
• Concise Synthesis of PM-94128 and Y-05460M-A
  作者：Masaru Enomoto、Shigefumi Kuwahara

  DOI：10.1021/jo9014968

  日期：2009.10.2

  The enantioselective total synthesis of PM-94128, a potent cytotoxin of microbial origin, was accomplished by a concise nine-step sequence of reactions in 14% overall yield from N-Boc-L-leucine. The synthesis of Y-05460M-A, a one-carbon lower homologue of PM-94128, was also achieved from N-BOC-L-valine by the same approach, which enabled its stereochemical determination.