2-((4-methylphenyl)sulfonyl)cyclopent-2-en-1-one | 100298-31-5

• 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: 2-((4-methylphenyl)sulfonyl)cyclopent-2-en-1-one
• 英文别名: 2-(4-methylphenyl)sulfonylcyclopent-2-en-1-one
• CAS: 100298-31-5
• 化学式: C₁₂H₁₂O₃S
• 分子量: 236.291
• InChiKey: KSDZUVSZYLBWME-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  16
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  59.6
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2-((4-methylphenyl)sulfonyl)cyclopent-2-en-1-one 在 copper(l) iodide 、 正丁基锂 、 titanium(III) chloride 、 甲基锂 、 银 、 sodium hydride 、 氯化铵 、 臭氧 、 间氯过氧苯甲酸 、 六甲基二硅氮烷 、 锌 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 38.25h， 生成 (8R,13S,14S)-3-methoxy-13-methyl-6,7,8,12,13,14,15,16-octahydro-cyclopenta[a]phenanthren-17-one
  参考文献：
  名称：

  Total synthesis of natural estrone and estradiol methyl ethers in extremely high enantiomeric purity via an asymmetric Michael addition to an unsaturated sulfoxide

  摘要：

  DOI：

  10.1021/ja00266a019
• 作为产物：
  描述：

  2-[(4-methylphenyl)sulfinyl]cyclopent-2-en-1-one 在 间氯过氧苯甲酸 作用下， 以 二氯甲烷 为溶剂， 反应 1.0h， 以87%的产率得到2-((4-methylphenyl)sulfonyl)cyclopent-2-en-1-one
  参考文献：
  名称：

  m-CPBA/KOH:  An Efficient Reagent for Nucleophilic Epoxidation of gem-Deactivated Olefins

  摘要：

  The m-chloroperoxybenzoate anion (generated from m-CPBA and bases such as K2CO3 or KOH) is a highly efficient nucleophilic epoxidating reagent for strongly deactivated olefins containing two electron-withdrawing groups at the same carbon, under mild conditions which affect neither other double bonds nor electrophilic oxidizable centers such as sulfoxides.

  DOI：

  10.1021/jo050131o

文献信息

• Synthesis of bicyclo[3.1.0]hexanones via 1,3-dipolar cycloaddition of diazoalkanes to homochiral α-sulfinyl-2-cyclopentenones
  作者：José Luis García Ruano、Marina Alonso、David Cruz、Alberto Fraile、M. Rosario Martín、M. Teresa Peromingo、Amelia Tito、Francisco Yuste

  DOI：10.1016/j.tet.2008.08.088

  日期：2008.11

  and controls the π-facial and endo/exo selectivities. The π-facial selectivity can be inverted in the presence of Yb(OTf)3, which makes possible the stereodivergent synthesis of both diastereoisomeric pyrazolines. Completely stereoselective denitrogenation of optically pure pyrazolines into cyclopropanes was achieved under substoichiometric Yb(OTf)3 catalysis.

  研究了重氮甲烷，重氮乙烷和（三甲基甲硅烷基）重氮甲烷与（S）-2-对甲苯亚磺酰基环戊-2-烯-1-酮的反应。亚磺酰基基团提高了反应性并控制了π界面和内/外选择性。可以在Yb（OTf）3存在的情况下反转π面选择性，这使得两种非对映异构吡唑啉的立体发散合成成为可能。在亚化学计量的Yb（OTf）3催化下实现了光学纯吡唑啉向立体丙烷的完全立体选择性脱氮。
• Towards the total synthesis of 9,11-secosterol: Linking A,B- and D-rings with Michael addition to sulfone-activated cyclopentenone
  作者：Marek Kõllo、Kristi Rõuk、Ivar Järving、Tõnis Pehk、Margus Lopp

  DOI：10.1016/j.tet.2023.133363

  日期：2023.3

  investigated using the following Michael acceptor - sulfone 2-[(4-methylphenyl)sulfonyl]cyclopent-2-en-1-one, where the addition product was isolated in good yield and as a mixture of two diastereomers. Also, the diastereomers were separable by crystallization, and, based on NMR spectroscopic data, the relative configuration of the formed stereocentres of the isolated diastereomer matched the 9,11-secosterol

  已使用以下迈克尔受体-砜 2-[(4-甲基苯基)磺酰基]环戊二烯-2-en-1-one 研究了迈克尔加成在构建 9,11-secosterols 碳骨架中的应用，其中加成产物以良好的收率分离，并且是两种非对映异构体的混合物。此外，非对映异构体可通过结晶分离，并且根据 NMR 光谱数据，分离的非对映异构体形成的立体中心的相对构型与自然界中发现的 9,11-仲甾醇相匹配。该研究可用于创建 9,11-二甾醇的全合成方案。
• Regio- and stereoselective synthesis of pyrrolo or azepine-fused cyclopenta[<i>d</i>]isoxazolines from 2-<i>p</i>-tolylsulfinylcyclopent-2-en-1-one
  作者：José L. García Ruano、José F. Soriano、Alberto Fraile、M. Rosario Martín、Alberto Núñez

  DOI：10.1080/17415993.2012.705286

  日期：2013.4.1

  Reactions of enantiopure 2-p-tolylsulfinylcyclopent-2-en-1-one with cyclic nitrones afforded pyrrolo or azepine-fused cyclopenta[d]isoxazolidines in high yields under mild conditions. Comparison of these results with those obtained with cyclopent-2-en-1-one as the dipolarophile shows that the sulfinyl group increases the reactivity of the enonic system and efficiently controls the pi-facial and endo/exo selectivities of the cycloadditions, which are also dependent on the easy cycloreversion of the resulting compounds. Results obtained in reactions with other dipoles (benzonitrile oxides and those resulting from allenoate and PPh3) are also reported.[GRAPHICS].
• Nucleophilic Epoxidation of α-Sulfonyl-α,β-Unsaturated Esters with <i>m</i>-CPBA
  作者：J. L. Garcća Ruano、C. Fajardo、A. Fraile、M. R. Martićn

  DOI：10.1080/10426500590913302

  日期：2005.3.2
• <i>m</i>-CPBA/KOH:  An Efficient Reagent for Nucleophilic Epoxidation of <i>g</i><i>em</i>-Deactivated Olefins
  作者：J. L. García Ruano、Cristina Fajardo、Alberto Fraile、M. Rosario Martín

  DOI：10.1021/jo050131o

  日期：2005.5.1

  The m-chloroperoxybenzoate anion (generated from m-CPBA and bases such as K2CO3 or KOH) is a highly efficient nucleophilic epoxidating reagent for strongly deactivated olefins containing two electron-withdrawing groups at the same carbon, under mild conditions which affect neither other double bonds nor electrophilic oxidizable centers such as sulfoxides.