tert-butyl 2,5-dihydro-4-(4-methoxyphenyl)-2-oxo-1H-pyrrole-1-carboxylate | 928215-95-6

• 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-4-(4-methoxyphenyl)-2-oxo-1H-pyrrole-1-carboxylate
• 英文别名: 1-Boc-4-(4-methoxyphenyl)-1H-pyrrol-2(5H)-one；tert-butyl 3-(4-methoxyphenyl)-5-oxo-2H-pyrrole-1-carboxylate
• CAS: 928215-95-6
• 化学式: C₁₆H₁₉NO₄
• 分子量: 289.331
• InChiKey: BMFSUPDVIDGURD-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  21
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  55.8
• 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-4-(4-methoxyphenyl)-2-oxo-1H-pyrrole-1-carboxylate 在 bis(norbornadiene)rhodium(l)tetrafluoroborate 、 zhaophos 、 氢气 作用下， 以 二氯甲烷 为溶剂， 35.0 ℃ 、6.08 MPa 条件下， 反应 48.0h， 以85%的产率得到tert-butyl (R)-4-(4-methoxyphenyl)-2-oxopyrrolidine-1-carboxylate
  参考文献：
  名称：

  Rh催化不对称加氢高对映选择性合成手性γ-内酰胺

  摘要：

  Rh /双膦-硫脲（ZhaoPhos）催化体系已被确定用于手性γ-内酰胺的直接不对称合成。将各种带有β-芳基或β-烷基取代基的无NH的α，β-不饱和内酰胺平滑氢化，以提供所需的γ-内酰胺，产率高达99％，对映体过量（ee）高达99％。该方法提供了合成手性γ-内酰胺或γ-氨基酸的高度实用的途径。

  DOI：

  10.1021/acscatal.8b00827
• 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-4-(4-methoxyphenyl)-2-oxo-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

• Suzuki-Miyaura arylations of tetramic acid sulfonates: Evaluation of lactam protection, sulfonate esters, and sterics
  作者：Sarah J. P. Yoon-Miller、Kathryn M. Dorward、Kimberly P. White、Erin T. Pelkey

  DOI：10.1002/jhet.96

  日期：2009.5

  The synthesis of 3,4-diaryl-3-pyrrolin-2-ones and 4-aryl-3-pyrrolin-2-ones using Suzuki–Miyaura cross-coupling reactions of tetramic acid sulfonates with arylboronic acids has been studied. The effect that sulfonate ester, sterics, and lactam protection has on the cross-coupling reaction was evaluated. As expected, triflates were better cross-coupling partners than the corresponding tosylates. The

  研究了使用四磺酸磺酸盐与芳基硼酸的Suzuki-Miyaura交叉偶联反应合成3,4-二芳基-3-吡咯啉-2-酮和4-芳基-3-吡咯啉-2-酮。评估了磺酸酯，空间位和内酰胺保护对交叉偶联反应的影响。不出所料，三氟甲磺酸酯比相应的甲苯磺酸盐更好地交叉偶联。在3-位引入芳基仅部分影响产率。重要的是，缺乏内酰胺保护基的四甲酸三氟甲磺酸酯（和较小程度的甲苯磺酸酯）仍然是有效的底物。J.杂环化​​学。，46，447（2009）。
• Rh–IndOlefOx catalyzed conjugate addition/Heck-type coupling of organoboronics to a lactam or a lactone
  作者：Noora Kuuloja、Matti Vaismaa、Robert Franzén

  DOI：10.1016/j.tet.2012.01.040

  日期：2012.3

  Four indole-olefin-oxazoline (IndOlefOx) ligands were synthesized and evaluated in Rh-catalyzed reactions between organoboronics and a lactam or a lactone. In addition to the expected conjugate addition products, the formation of significant amounts of Heck-type products was observed. The scope and limitations of these reactions were investigated. (C) 2012 Elsevier Ltd. All rights reserved.
• Highly Enantioselective Synthesis of Chiral γ-Lactams by Rh-Catalyzed Asymmetric Hydrogenation
  作者：Qiwei Lang、Guoxian Gu、Yaoti Cheng、Qin Yin、Xumu Zhang

  DOI：10.1021/acscatal.8b00827

  日期：2018.6.1

  a (ZhaoPhos) catalytic system has been identified for the straightforward asymmetric synthesis of chiral γ-lactams. A variety of NH free α,β-unsaturated lactams bearing a β-aryl or β-alkyl substituent were smoothly hydrogenated to provide the desired γ-lactams in up to 99% yield and 99% enantiomeric excess (ee). This methodology provides a highly practical pathway to synthesize chiral γ-lactams or

  Rh /双膦-硫脲（ZhaoPhos）催化体系已被确定用于手性γ-内酰胺的直接不对称合成。将各种带有β-芳基或β-烷基取代基的无NH的α，β-不饱和内酰胺平滑氢化，以提供所需的γ-内酰胺，产率高达99％，对映体过量（ee）高达99％。该方法提供了合成手性γ-内酰胺或γ-氨基酸的高度实用的途径。
• 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.