1-benzyl-4-methoxy-1H-pyrrol-2(5H)-one | 90968-37-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 1-benzyl-4-methoxy-1H-pyrrol-2(5H)-one
• 英文别名: 1-Benzyl-4-methoxy-Δ³-pyrrolin-2-one；N-benzyl-4-O-methyl tetramate；1-benzyl-4-methoxy-3-pyrrolin-2-one；1-benzyl-4-hydroxy-1,5-dihydro-pyrrol-2-one；1-benzyl-4-methoxy-1,5-dihydro-2H-pyrrol-2-one；1-benzyl-3-methoxy-2H-pyrrol-5-one
• CAS: 90968-37-9
• 化学式: C₁₂H₁₃NO₂
• 分子量: 203.241
• InChiKey: KGTDFIJEFHIKSO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1
• 重原子数：
  15
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  29.5
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  1-benzyl-4-methoxy-1H-pyrrol-2(5H)-one 在 硫酸 作用下， 以 水 为溶剂， 反应 3.0h， 以62%的产率得到1-苄基吡咯烷-2,4-二酮
  参考文献：
  名称：

  钯催化的吡啶基化乙烯基酰胺和尿素的环羰基化反应生成环融合的嘧啶并嘧啶酮

  摘要：

  作为旨在产生用于药物化学探索的新杂环框架的计划的一部分，采取了一种有效的方法来组装新型环稠合的嘧啶并嘧啶酮。具体而言，收集了11 H-吡啶并[ 2,1 - b ]喹唑啉-1,11 （2 H）-二酮和2,3-二氢吡啶并[ 1,2- a ]吡咯并[3,4- d ]嘧啶-通过钯催化的2-吡啶基连接的乙烯基酰胺和脲的钯催化，吡啶定向的环羰基化反应生成1,10-二酮，收率高达90％。

  DOI：

  10.1021/acs.orglett.8b01275
• 作为产物：
  描述：

  4-溴-3-甲氧基-2-丁烯酸甲酯 在 氢氧化钾 、 ammonium hydroxide 、 四丁基硫酸氢铵 作用下， 以 四氢呋喃 为溶剂， 反应 12.0h， 生成 1-benzyl-4-methoxy-1H-pyrrol-2(5H)-one
  参考文献：
  名称：

  Synthesis of 5-substituted 4--methyl tetramates

  摘要：

  DOI：

  10.1016/s0040-4039(00)85192-8

文献信息

• Preparation and Intramolecular [2+2]-Photocycloaddition of 1,5-Dihydropyrrol-2-ones and 5,6-Dihydro-1<i>H</i>-pyridin-2-ones with C-, N-, and O-linked Alkenyl Side Chains at the 4-Position
  作者：Dominik Albrecht、Birte Basler、Thorsten Bach

  DOI：10.1021/jo7027129

  日期：2008.3.1

  ion include the use of dichloromethane as the solvent and an irradiation with a mercury low-pressure lamp (λ = 254 nm). Upon applying these conditions at ambient temperature, the corresponding intramolecular photocycloaddition products 28−37 were obtained in good yields (52−79%) and with perfect diastereoselectivity. The constitution and configuration of the products was elucidated by NMR-spectroscopy

  1,5-二氢吡咯-2-酮2，6，9，和11（从甲基tetramates制备1A - Ç），Ñ -Boc保护的特特拉姆酸（3），或ñ -Boc保护的特特拉姆酸溴化物（7）以短的反应顺序和非常好的总产率。同源5,6-二氢-1- ħ -吡啶-2-酮16，18，20，21，23，和27分别沿着从哌啶-2,4-二酮起始类似途径制备（19），或者从它的ñ -叔丁基衍生物15。[2 + 2]-光环加成反应的最佳条件包括使用二氯甲烷作为溶剂和用汞低压灯（λ= 254 nm）照射。当在环境温度下施加这些条件下，相应的分子内光环产品28 - 37以良好的收率（52-79％）中，用非对映选择性完美得到。通过NMR光谱阐明了产物的组成和构型。对于O系衬底2a和20，观察到光环加成率随温度强烈降低。的效果不太明显了N-和C-拴基板6，9，23，和27。使用手性络合剂实现对映选择性反应似乎是可行的。然而，络合剂（-）-
• Regioselective Reduction of 3-Methoxymaleimides:  An Efficient Method for the Synthesis of Methyl 5-Hydroxytetramates
  作者：Fatiah Issa、Joshua Fischer、Peter Turner、Mark J. Coster

  DOI：10.1021/jo0605750

  日期：2006.6.1

  various N-alkyl-3-methoxymaleimides, synthesized by base-promoted N-alkylation of 3-methoxymaleimide, were reduced using sodium borohydride with complete regioselectivity. The resultant methyl 5-hydroxytetramates are useful intermediates in the synthesis of a variety of tetramate derivatives.

  使用硼氢化钠以完全的区域选择性还原由3-甲氧基马来酰亚胺的碱促进的N-烷基化反应而合成的3-甲氧基马来酰亚胺和各种N-烷基-3-甲氧基马来酰亚胺。所得的5-羟基四氢甲酸甲酯是合成各种四氢呋喃衍生物的有用中间体。
• Synthesis and Protein Kinase C Inhibitory Activities of Acyclic Balanol Analogs That Are Highly Selective for Protein Kinase C over Protein Kinase A
  作者：Jean M. Defauw、Marcia M. Murphy、G. Erik Jagdmann、Hong Hu、John W. Lampe、Sean P. Hollinshead、Thomas J. Mitchell、Heidi M. Crane、Julia M. Heerding、José S. Mendoza、Jefferson E. Davis、James W. Darges、Frederick R. Hubbard、Steven E. Hall

  DOI：10.1021/jm960581w

  日期：1996.1.1

  A series of balanol analogs in which the perhydroazepine ring and the p-hydroxybenzamide moiety were combined into an acyclic linked unit have been prepared and evaluated for their inhibitory properties against the serine/threonine kinase PKC. Several low-micromolar to low-nanomolar inhibitors of the alpha, beta(I), beta(II), gamma, delta, epsilon, and eta PKC: isozymes were prepared. In general, these acyclic balanol analogs were found to be highly selective for PKC over the serine/threonine kinase PKA. The type and number of atoms linking the benzophenone ester to the p-hydroxyphenyl group necessary for optimal PKC inhibition were investigated. The most potent compounds contained a three-carbon linker in which the carboxamide moiety of balanol had been replaced by a methylene group. The effect of placing substituents on the three-carbon chain was also investigated. The preferred compounds contained either a 2-benzenesulfonamido (6b) or a 1-methyl (21b) substituent. The preferred compounds 6b and 21b were tested against a panel of serine/threonine kinases and found to be highly selective for PKC. The more active enantiomer of 6b, (S)-12b, was 3-10-fold more active than the R-enantiomer against the PKC isozymes. The effect of making the analogs more rigid by making the three-carbon chain part of a five-membered ring, but with retention of the methylene replacement for the carboxamide moiety, led to potent PKC inhibitors including anti-substituted pyrrolidine analog 35b and the most potent PKC inhibitor in the series, anti-substituted cyclopentane analog 29b. The anti cyclopentane analog 29b was a low-micromolar inhibitor of the PMA-induced superoxide burst in neutrophils, and its carboxylic ester was a high-nanomolar inhibitor of neutrophils. Finally esterification of 21b, (S)-12b, and 35b turned these potent PKC inhibitors into low-micromolar inhibitors of neutrophils.
• Jones, Raymond C. F.; Patience, Jacqueline M., Journal of the Chemical Society. Perkin transactions I, 1990, # 8, p. 2350 - 2351
  作者：Jones, Raymond C. F.、Patience, Jacqueline M.

  DOI：——

  日期：——
• Synthesis of 4-alkoxy-Δ3-pyrrolin-2-ones and tetramic acids
  作者：Kanwarpal S Kochhar、Holly J Carson、Kimberly A Clouser、John W Elling、Lauren A Gramens、Judith L Parry、Helayne L Sherman、Kevin Braat、Harold W Pinnick

  DOI：10.1016/s0040-4039(01)90063-2

  日期：1984.1