1-benzenesulfonyl-2-methylcyclopentane

• 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-benzenesulfonyl-2-methylcyclopentane
• 英文别名: [(1R,2R)-2-methylcyclopentyl]sulfonylbenzene
• 化学式: C₁₂H₁₆O₂S
• 分子量: 224.324
• InChiKey: AVHFOYNUUPLEDH-ZYHUDNBSSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  15
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  42.5
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  1-benzenesulfonyl-2-methylcyclopentane 、 二溴甲烷 、 正丁基锂 生成 1-methyl-1-bromomethylene-cyclopentane
  参考文献：
  名称：

  CHARREAU, PHILIPPE;JULIA, MARC;VERPEAUX, JEAN-NOEL, J. ORGANOMET. CHEM., 379,(1989) N, C. 201-210

  摘要：

  DOI：
• 作为产物：
  描述：

  1-甲基环戊烯 在 偶氮二异丁腈 、 sodium n-propoxide 、 双氧水 、 溶剂黄146 作用下， 生成 1-benzenesulfonyl-2-methylcyclopentane
  参考文献：
  名称：

  The Stereochemistry of the Nucleophilic Addition of p-Toluenethiol to 1-p-Tolylsulfonylcyclopentene¹

  摘要：

  DOI：

  10.1021/jo01038a018

文献信息

• Radical rearrangements of α-iodoalkyl phenyl sulfones involving 1,5 hydrogen atom transfer reactions
  作者：Marek Masnyk

  DOI：10.1016/s0040-4039(96)02430-6

  日期：1997.2

  α-Iodoalkyl phenyl sulfones undergo radical rearrangement to 5-iodo-1-phenylsulfonyl derivatives when heated with benzoyl peroxide or when irradiated with a sunlamp in the presence of hexabutylditin. Products of these rearrangements, upon treatment with bases, can be easily and stereoselectively converted into trans phenylsulfonyl derivatives of cyclopentane.

  当与过氧化苯甲酰一起加热或在六丁基二锡的存在下用日光灯照射时，α-碘代烷基苯基砜会发生自由基重排，生成5-碘-1-苯基磺酰基衍生物。用碱处理后，这些重排的产物可以容易地和立体选择性地转化为环戊烷的反式苯磺酰基衍生物。
• The study of intramolecular free radical cyclizations of α-sulfonyl and α-sulfinyl radicals
  作者：Tsai Yeun-Min、Ke Bor-Wen、Lin Chao-Hsiung

  DOI：10.1016/s0040-4039(00)98025-0

  日期：1990.1

  α-Sulfonyl and α-sulfinyl radicals can be generated from the corresponding α-halosulfones and αhalosulfoxides. Our results indicate that these radicals cyclize very efficiently.

  α-磺酰基和α-亚磺酰基基团可以由相应的α-卤代砜和α卤代亚砜生成。我们的结果表明，这些自由基非常有效地环化。
• Applications of highly enantioenriched alcohols bearing a phenylthio group in the preparation of ring compounds. The two-pot synthesis of an enantiopure spiroacetal pheromone bearing three chiral centers
  作者：Theodore Cohen、Shaojing Tong

  DOI：10.1016/s0040-4020(97)00635-2

  日期：1997.7

  The new chiron (S)-6-phenylthio-2-hexanol (3) was prepared in high enantiomeric excess by baker's yeast reduction of the corresponding ketone. Enantioenriched alcohols 1, 2 and 3, prepared previously by a similar procedure, or their racemic counterparts, were transformed into ring closed compounds 5-methyl-2-(phenylthio)tetrahydrofuran (9), 6-methyl-2-(phenylthio)tetrahydropyran (10), 2-methyl-1-phenylsulfonyl cyclopropane (14), cyclobutane (15), cyclopentane (16), and a bee pheromone, (2S,6R,8S)-2,8-dimethyl-1,7-dioxaspiro[5.5]undecane (20). (C) 1997 Elsevier Science Ltd.
• Generation and intramolecular cyclization of α-sulfinyl and α-sulfonyl radicals
  作者：Bor-Wen Ke、Chao-Hsiung Lin、Yeun-Min Tsai

  DOI：10.1016/s0040-4020(97)00472-9

  日期：1997.6

  alpha-Phenylsulfinyl and alpha-Phenylsulfonyl radicals are generated by the reactions of alpha-chlorosulfoxides and alpha-chlorosulfones with tributyltin hydride, respectively. High reaction concentration (0.2 M) is required to ensure efficient generations of these radicals. The 5-exo-type intramolecular cyclizations of these radicals are studied. The cyclization is most successful when the olefin is terminally substituted with an ester group. The sulfinyl group only induces mild diastereoselectivity on the cyclization. (C) 1997 Elsevier Science Ltd.
• α-Sulfonyl radical initiated intramolecular tandem radical cyclization
  作者：Vichai Reutrakul、Chompoonut Poolsanong、Manat Pohmakotr

  DOI：10.1016/s0040-4039(01)93387-8

  日期：1989.1