<(phenylthio)methyl>cyclopentane | 100258-36-4

• 分子结构分类: 有机化合物 - 有机硫化合物 - 硫醚类
• 英文名称: <(phenylthio)methyl>cyclopentane
• 英文别名: cyclopentylmethyl phenyl sulfide；(phenylthiomethyl)cyclopentane；cyclopentylmethyl-phenyl sulfide；Cyclopentylmethyl-phenyl-sulfid；Benzene, [(cyclopentylmethyl)thio]-；cyclopentylmethylsulfanylbenzene
• CAS: 100258-36-4
• 化学式: C₁₂H₁₆S
• 分子量: 192.325
• InChiKey: CMPRNSUETKJLSX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.3
• 重原子数：
  13
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  25.3
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  <(phenylthio)methyl>cyclopentane 在 N-氯代丁二酰亚胺 作用下， 以 四氯化碳 为溶剂， 生成 (Chloro-cyclopentyl-methylsulfanyl)-benzene
  参考文献：
  名称：

  Ring expansion or spirocyclisation of (phenylthiomethylene)cycloalkanes with aluminium chloride viaβ-thio carbocations

  摘要：

  标题反应可以用δ-硫代碳基（噻吩离子）到δ-硫代碳基的瓦格纳-梅尔韦恩重排来解释；这种不寻常的反应性可能是由于氯化铝的超亲电活化作用。

  DOI：

  10.1039/c39950000993
• 作为产物：
  描述：

  Cyclohexyl phenyl sulfide 生成 <(phenylthio)methyl>cyclopentane
  参考文献：
  名称：

  SISKIN, MICHAEL;BRONS, GLEN;KATRITZKY, ALAN R.;MURAGAN, RAMIAH, ENERGY AND FUELS, 4,(1990) N, C. 482-488

  摘要：

  DOI：

文献信息

• Reactions of alkylmercurials with heteroatom-centered acceptor radicals
  作者：Glen A. Russell、Preecha. Ngoviwatchai、Hasan I. Tashtoush、Anna. Pla-Dalmau、Rajive K. Khanna

  DOI：10.1021/ja00219a030

  日期：1988.5

  En particulier, reactivite relative de chlorures d'alkylmercures vis-a-vis de PhS • , PhSe • et I • generes a partir du disulfure de phenyle, diseleniure de phenyle et du β-iodo styrene ou du (diphenyl-1,1 iodo-2) ethylene

  En 特别，反应性相对于 de PhS • , PhSe • et I • 与 de PhS • , PhSe • et I • 属 a partir du disulfure de phenyle, diseleniure de phenyle et du β-iodo 苯乙烯 ou du (diphenyl-1,1 iodo -2) 乙烯
• Nickel-Catalyzed C–S Reductive Cross-Coupling of Alkyl Halides with Arylthiosilanes toward Alkyl Aryl Thioethers
  作者：Yu-Zhong Yang、Yang Li、Gui-Fen Lv、De-Liang He、Jin-Heng Li

  DOI：10.1021/acs.orglett.2c01954

  日期：2022.7.22

  A nickel-catalyzed C–S reductive cross-coupling of alkyl halides with arylthiosilanes for producing alkyl aryl thioethers is developed. This reaction is initiated by umpolung transformations of arylthiosilanes followed by C–S reductive cross-coupling with alkyl halides to manage an electrophilic alkyl group onto the electrophilic sulfur atom and then construct a C(sp3)–S bond, and features exquisite

  开发了一种镍催化的烷基卤化物与芳基硫硅烷的 C-S 还原交叉偶联，用于生产烷基芳基硫醚。该反应由芳基硫硅烷的 umpolung 转变引发，然后与卤代烷发生 C-S 还原交叉偶联，将亲电烷基控制在亲电硫原子上，然后构建 C(sp 3 )-S 键，具有出色的化学选择性，对多种官能团具有优异的耐受性，并广泛应用于生物相关分子的后期修饰。
• Nickel‐catalyzed umpolung C S radical reductive cross coupling of S‐(trifluoromethyl)arylsulfonothioates with alkyl halides
  作者：Yu-Zhong Yang、Gui-Fen Lv、Ming Hu、Yang Li、Jin-Heng Li

  DOI：10.1016/j.cclet.2023.108590

  日期：2023.11

  A new cooperative nickel reductive catalysis and N,N-dimethylformamide-mediated strategy for umpolung CS radical reductive cross coupling of S-(trifluoromethyl)arylsulfonothioates with alkyl halides to produce alkyl aryl thioethers is described. This reaction features excellent selectivity, wide functionality tolerance, broad substrate scope, and facile late-stage modification of biologically relevant

  描述了一种新的协同镍还原催化和N,N-二甲基甲酰胺介导的策略，用于S- (三氟甲基)芳基硫代磺酸酯与烷基卤的 C S 自由基还原交叉偶联生产烷基芳基硫醚。该反应具有优异的选择性、广泛的功能耐受性、广泛的底物范围以及易于对生物相关分子进行后期修饰。机理研究认识到，通过用 Sn 热诱导 DMF还原，最初生成酰胺自由基阴离子，然后进行反极化还原和亲核磺酰基部分的单电子转移，形成巯基自由基并与 Ni 0 /Ni I /Ni III接合/Ni I催化循环。
• Intramolecular Carbozincation of Unactivated Alkenes Occurs through a Zinc Radical Transfer Mechanism
  作者：Theodore Cohen、Heather Gibney、Roman Ivanov、Edmund A.-H. Yeh、Ilan Marek、Dennis P. Curran

  DOI：10.1021/ja076554k

  日期：2007.12.1

  The cyclizations of a number of terminally unsaturated alkenyl zinc iodides to cyclopentylmethylzinc iodides, formerly believed to be nonradical in nature, have been revealed as radical chain cyclizations initiated by adventitious oxygen. Five cases are presented in which the published carbozincation cis/trans selectivities are essentially the same as those found for the cyclizations of the unsaturated alkyl iodide precursors of the, alkylzinc iodides by the iodine atom transfer method at approximately the same temperatures. In addition, it has been found that one of the organozinc cyclizations does not occur in a system in which oxygen has been rigorously excluded. The combined findings strongly suggest that these organozinc cyclizations occur by a zinc radical transfer mechanism rather than by a conventional carbometallation that is thought to occur with the analogous organolithium and organomagnesium cyclizations.
• Free-radical chain-substitution reactions of alkylmercury halides
  作者：Glen A. Russell、Hasan Tashtoush

  DOI：10.1021/ja00343a069

  日期：1983.3