tert-butyl 2,5-dihydro-2-oxo-4-(thiophen-2-yl)-1H-pyrrole-1-carboxylate | 928215-98-9

• 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 2,5-dihydro-2-oxo-4-(thiophen-2-yl)-1H-pyrrole-1-carboxylate
• 英文别名: tert-butyl 5-oxo-3-thiophen-2-yl-2H-pyrrole-1-carboxylate
• CAS: 928215-98-9
• 化学式: C₁₃H₁₅NO₃S
• 分子量: 265.333
• InChiKey: XZRGFWLWVXJNRR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  18
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  74.8
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  tert-butyl 2,5-dihydro-2-oxo-4-(thiophen-2-yl)-1H-pyrrole-1-carboxylate 在 三氟乙酸 作用下， 以 二氯甲烷 为溶剂， 以98%的产率得到4-(thiophen-2-yl)-1H-pyrrol-2(5H)-one
  参考文献：
  名称：

  Short synthesis of 4-aryl-3-pyrrolin-2-ones

  摘要：

  A three step, convergent synthesis of 4-aryl-3-pyrrolin-2-ones from a tetramic acid has been developed. The key transformation utilized a Suzuki-Miyaura cross-coupling reaction between a 4-tosyloxy-3-pyrrolin-2-one and an arylboronic acid. This work also provides access to 4-arylpyrrolidin-2-ones, cyclic analogs of gamma-aminobutyric acid (GABA). Hydrogenation of 4-(4'-chloro-phenyl)-3-pyrrolin-2-one proceeded smoothly to give baclofen lactam. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2006.11.156
• 作为产物：
  描述：

  2,5-二氢-4-羟基-2-氧代-1H-吡咯-1-甲酸叔丁酯 在 (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride caesium carbonate 、 N,N-二异丙基乙胺 作用下， 以 四氢呋喃 、 二氯甲烷 、 水 为溶剂， 生成 tert-butyl 2,5-dihydro-2-oxo-4-(thiophen-2-yl)-1H-pyrrole-1-carboxylate
  参考文献：
  名称：

  Short synthesis of 4-aryl-3-pyrrolin-2-ones

  摘要：

  A three step, convergent synthesis of 4-aryl-3-pyrrolin-2-ones from a tetramic acid has been developed. The key transformation utilized a Suzuki-Miyaura cross-coupling reaction between a 4-tosyloxy-3-pyrrolin-2-one and an arylboronic acid. This work also provides access to 4-arylpyrrolidin-2-ones, cyclic analogs of gamma-aminobutyric acid (GABA). Hydrogenation of 4-(4'-chloro-phenyl)-3-pyrrolin-2-one proceeded smoothly to give baclofen lactam. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2006.11.156

文献信息

• Short synthesis of 4-aryl-3-pyrrolin-2-ones
  作者：Sarah J.P. Yoon-Miller、Suzanne M. Opalka、Erin T. Pelkey

  DOI：10.1016/j.tetlet.2006.11.156

  日期：2007.1

  A three step, convergent synthesis of 4-aryl-3-pyrrolin-2-ones from a tetramic acid has been developed. The key transformation utilized a Suzuki-Miyaura cross-coupling reaction between a 4-tosyloxy-3-pyrrolin-2-one and an arylboronic acid. This work also provides access to 4-arylpyrrolidin-2-ones, cyclic analogs of gamma-aminobutyric acid (GABA). Hydrogenation of 4-(4'-chloro-phenyl)-3-pyrrolin-2-one proceeded smoothly to give baclofen lactam. (c) 2006 Elsevier Ltd. All rights reserved.