1-(4-methoxyphenyl)-4-phenylpyrrolidin-2-one | 174618-43-0

• 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: 1-(4-methoxyphenyl)-4-phenylpyrrolidin-2-one
• 英文别名: (S)-1-(4-methoxyphenyl)-4-phenylpyrrolidin-2-one；(4S)-1-(4-methoxyphenyl)-4-phenylpyrrolidin-2-one
• CAS: 174618-43-0
• 化学式: C₁₇H₁₇NO₂
• 分子量: 267.327
• InChiKey: HDKMEHXJRVFDMK-CQSZACIVSA-N

物化性质

• 熔点：
  92.5-95 °C(Solv: ethyl acetate (141-78-6); ligroine (8032-32-4))
• 沸点：
  504.6±50.0 °C(Predicted)
• 密度：
  1.169±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.22
• 重原子数：
  20.0
• 可旋转键数：
  3.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.24
• 拓扑面积：
  29.54
• 氢给体数：
  0.0
• 氢受体数：
  2.0

反应信息

• 作为反应物：
  描述：

  1-(4-methoxyphenyl)-4-phenylpyrrolidin-2-one 在 ammonium cerium(IV) nitrate 作用下， 以 水 、 乙腈 为溶剂， 生成 (S)-4-phenylpyrrolidin-2-one
  参考文献：
  名称：

  Rh 2（OAc）4催化CH在手性酯重氮苯胺中的插入

  摘要：

  研究了Rh 2（OAc）4催化的手性酯重氮苯胺化物中的CH插入反应，发现该化合物在脱碳烷氧基化后可产生具有中等至较高ee（37-98％）的4-取代的2-吡咯烷酮。发现在影响N-芳基乙基重氮苯胺中反应的对映选择性方面，电子效应与空间效应相反。

  DOI：

  10.1016/0040-4039(95)02115-9
• 作为产物：
  描述：

  2-Diazo-N-(4-methoxy-phenyl)-N-phenethyl-malonamic acid (1R,2S,3S,4R)-4,7,7-trimethyl-3-naphthalen-1-yl-bicyclo[2.2.1]hept-2-yl ester 在 dirhodium tetraacetate 、 sodium chloride 作用下， 以 二氯甲烷 、 水 、 二甲基亚砜 为溶剂， 生成 1-(4-methoxyphenyl)-4-phenylpyrrolidin-2-one
  参考文献：
  名称：

  Rh 2（OAc）4催化CH在手性酯重氮苯胺中的插入

  摘要：

  研究了Rh 2（OAc）4催化的手性酯重氮苯胺化物中的CH插入反应，发现该化合物在脱碳烷氧基化后可产生具有中等至较高ee（37-98％）的4-取代的2-吡咯烷酮。发现在影响N-芳基乙基重氮苯胺中反应的对映选择性方面，电子效应与空间效应相反。

  DOI：

  10.1016/0040-4039(95)02115-9

文献信息

• 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。
• Lewis Base‐Catalysed Enantioselective Radical Conjugate Addition for the Synthesis of Enantioenriched Pyrrolidinones
  作者：Will C. Hartley、Florian Schiel、Elena Ermini、Paolo Melchiorre

  DOI：10.1002/anie.202204735

  日期：2022.6.27

  to realise the first example of asymmetric radical conjugate addition to α,β-unsaturated anhydrides and esters. The chemistry, mastered by a chiral isothiourea organocatalyst, enables the synthesis of enantioenriched pyrrolidinones, with application to the synthesis of biologically-active γ-amino butyric acids.

  已经开发了光氧化还原催化和路易斯碱催化的组合，以实现不对称自由基共轭加成到 α,β-不饱和酸酐和酯的第一个例子。该化学由手性异硫脲有机催化剂掌握，能够合成富含对映体的吡咯烷酮，并应用于合成具有生物活性的 γ-氨基丁酸。
• Asymmetric Synthesis of β-Substituted γ-Lactams via Rhodium/Diene-Catalyzed 1,4-Additions: Application to the Synthesis of (<i>R</i>)-Baclofen and (<i>R</i>)-Rolipram
  作者：Cheng Shao、Hong-Jie Yu、Nuo-Yi Wu、Ping Tian、Rui Wang、Chen-Guo Feng、Guo-Qiang Lin

  DOI：10.1021/ol103054a

  日期：2011.2.18

  An efficient rhodium/diene-catalyzed asymmetric addition of arylboronic acids to alpha,beta-unsaturated gamma-lactams has been developed. The power of this methodology is further demonstrated by the concise synthesis of (R)-baclofen and (R)-rolipram.
• Steric and Electronic Influences on the Diastereoselectivity of the Rh₂(OAc)₄-Catalyzed C−H Insertion in Chiral Ester Diazoanilides:  Synthesis of Chiral, Nonracemic 4-Substituted 2-Pyrrolidinones
  作者：Andrew G. H. Wee、Baosheng Liu、Douglas D. McLeod

  DOI：10.1021/jo971540q

  日期：1998.6.1

  A series of N-substituted N-(4-methoxyphenyl)-alpha-(alkoxycarbonyl)-alpha-diazoacetanilides, 10 and ent-10, wherein the alkoxy unit is a chiral auxiliary group [(-)-7 or (+)-8)], was prepared. The Rh-2(OAc)(4)-catalyzed intramolecular C-H insertion reaction of 10 and ent-10, under optimized reaction conditions, was investigated as a route for the preparation of chiral, nonracemic 4-substituted 2-pyrrolidinones. The cyclization reaction led only to 2-pyrrolidinone and 2-azetidinone products; the former products were obtained as major and, in a few cases, as exclusive products. The type and nature of the N-substituent in 10 or ent-10 was found to govern the diastereoselectivity of the reaction. With N-alkyl groups, steric effects play an important role in determining the diastereoselectivity of the reaction. However, with N-arylethyl substituents, electronic effects transmitted by the aryl substituents influenced the diastereoselectivity of the C-H insertion reaction. Specifically, electron-donating substituents were found to markedly attenuate the diastereoselectivity of the reaction. The diastereoselectivity of the reaction ranged from moderate to high (37-98%). A transition-state model to explain the observed diastereoselectivity is provided. The synthetic utility of the method is demonstrated by the stereoselective synthesis of the medicinally important, unnatural amino acid trans-4-cyclohexyl-L-proline 23.